Vitamin d3-like compound

A method for producing a compound of Formula (1) below, the method comprising:

• allowing a compound of Formula (7) below to react with a compound of Formula (8) below to form a compound of Formula (9) below;
• and
• removing groups represented by W from the compound of Formula (9) to form the compound of Formula (1),
• wherein m and n are independently 0 or 1, p is an integer of 0 to 4, s is an integer of 0 to 4, Y is an oxygen atom, a sulfur atom, or a divalent group represented by —NR6—, R1 is a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms, R2 is an alkyl group having 1 to 8 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 8 carbon atoms, or a halogen atom, R3 is a linear or branched, saturated or unsaturated, divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, optionally having a substituent, and optionally having a heteroatom-containing carbon chain, R4 is a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms, R5 is a hydrogen atom, a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms and optionally having a substituent, or a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms and optionally having a substituent, R6 is a hydrogen atom or a monovalent aliphatic hydrocarbon group, and R7 and R8 are simultaneously hydrogen atoms or combined to form a methylidene group,
• wherein m, n, p, s, Y, R1, R2, R3, R4, and R6 are as defined above, W is a protecting group, and Z1 is a halogen atom or a group represented by Formula (3) below,
• wherein * indicates a bond,
• wherein R5, R7, R8, and W are as defined above, and Z2 is a halogen atom or a group represented by Formula (3), provided that when Z1 in Formula (7) is a halogen atom, Z2 is a group represented by Formula (3) and that when Z1 in Formula (7) is a group represented by Formula (3), Z2 is a halogen atom,
• wherein m, n, p, s, W, Y, R1, R2, R3, R4, R5, R6, R7, and R8 are as defined above.

A method for producing a compound of Formula (13) below, the method comprising:

• allowing a compound of Formula (10) below to react with a compound of Formula (8) below to form a compound of Formula (11) below;
• obtaining a compound of Formula (12) below from the compound of Formula (11);
• and
• removing groups represented by W from the compound of Formula (12) to form the compound of Formula (13),
• wherein m is 0 or 1, p is an integer of 0 to 4, s is an integer of 0 to 4, Y is an oxygen atom, a sulfur atom, or a divalent group represented by —NR6—, R1 is a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms, R2 is an alkyl group having 1 to 8 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 8 carbon atoms, or a halogen atom, R4 is a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms, R5 is a hydrogen atom, a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms and optionally having a substituent, or a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms and optionally having a substituent, R6 is a hydrogen atom or a monovalent aliphatic hydrocarbon group, R7 and R8 are simultaneously hydrogen atoms or combined to form a methylidene group, and R9 is a linear or branched, saturated or unsaturated, divalent aliphatic hydrocarbon group having 1 to 19 carbon atoms, optionally having a substituent, and optionally having a heteroatom-containing carbon chain,
• wherein m, p, s, Y, R1, R2, R4, R6, R9, and R10 are as defined above, R10 is an alkyl group having 1 to 8 carbon atoms, and Z1 is a halogen atom or a group represented by Formula (3) below,
• wherein * indicates a bond,
• wherein R5, R7, and R8 are as defined above, W is a protecting group, and Z2 is a halogen atom or a group represented by Formula (3), provided that when Z1 in Formula (10) is a halogen atom, Z2 is a group represented by Formula (3) and that when Z1 in Formula (10) is a group represented by Formula (3), Z2 is a halogen atom,
• wherein m, p, s, W, Y, R1, R2, R4, R5, R6, R7, R8, R9, and R10 are as defined above,
• wherein m, p, s, W, Y, R1, R2, R4, R5, R6, R7, R8, and R9 are as defined above.

A method for producing a compound of Formula (16) below, the method comprising:

• allowing a compound of Formula (14) below to react with a compound of Formula (8) below to form a compound of Formula (15) below;
• and
• removing groups represented by W from the compound of Formula (15) to form the compound of Formula (16),
• wherein p is an integer of 0 to 4, s is an integer of 0 to 4, R1 is a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms, R2 is an alkyl group having 1 to 8 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 8 carbon atoms, or a halogen atom, R4 is a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms, R5 is a hydrogen atom, a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms and optionally having a substituent, or a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms and optionally having a substituent, and R7 and R8 are simultaneously hydrogen atoms or combined to form a methylidene group,
• wherein p, s, R1, R2, and R4 are as defined above, and Z1 is a halogen atom or a group represented by Formula (3) below,
• wherein * indicates a bond,
• wherein R5, R7, and R8 are as defined above, W is a protecting group, and Z2 is a halogen atom or a group represented by Formula (3), provided that when Z1 in Formula (14) is a halogen atom, Z2 is a group represented by Formula (3) and that when Z1 in Formula (14) is a group represented by Formula (3), Z2 is a halogen atom,
• wherein p, s, W, R1, R2, R4, R5, R7, and R8 are as defined above.

A method for producing a compound of Formula (19) below, the method comprising:

• allowing a compound of Formula (6) below to react with a compound of Formula (17) below to form a compound of Formula (18) below;
• and
• removing groups represented by W from the compound of Formula (18) to form the compound of Formula (19),
• wherein m and n are independently 0 or 1, p is an integer of 0 to 4, s is an integer of 0 to 4, Y is an oxygen atom, a sulfur atom, or a divalent group represented by —NR6—, R1 is a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms, R2 is an alkyl group having 1 to 8 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 8 carbon atoms, or a halogen atom, R3 is a linear or branched, saturated or unsaturated, divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, optionally having a substituent, and optionally having a heteroatom-containing carbon chain, R4 is a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms, R5 is a hydrogen atom, a hydroxyl group, an alkoxy group having 1 to 6 carbon atoms and optionally having a substituent, or a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms and optionally having a substituent, and R6 is a hydrogen atom or a monovalent aliphatic hydrocarbon group,
• wherein m, n, p, s, Y, R1, R2, R3, R4, and R6 are as defined above, and W is a protecting group,
• wherein R5 and W are as defined above, and R11 and R12 are independently a monovalent hydrocarbon group having 1 to 20 carbon atoms,
• wherein m, n, p, s, W, Y, R1, R2, R3, R4, R5, and R6 are as defined above.

A method for producing a compound of Formula (23) below, the method comprising:

• allowing a compound of Formula (7) below to react with a compound of Formula (20) below to form a compound of Formula (21) below;
• obtaining a compound of Formula (22) below from the compound of Formula (21);
• and
• removing a group represented by W from the compound of Formula (22) to form the compound of Formula (23),
• wherein m and n are independently 0 or 1, p is an integer of 0 to 4, s is an integer of 0 to 4, Y is an oxygen atom, a sulfur atom, or a divalent group represented by —NR6—, R1 is a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms, R2 is an alkyl group having 1 to 8 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 8 carbon atoms, or a halogen atom, R3 is a linear or branched, saturated or unsaturated, divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, optionally having a substituent, and optionally having a heteroatom-containing carbon chain, R4 is a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms, R6 is a hydrogen atom or a monovalent aliphatic hydrocarbon group, R7 and R8 are simultaneously hydrogen atoms or combined to form a methylidene group, and R13 is a linear or branched, saturated or unsaturated, divalent aliphatic hydrocarbon group having 1 to 4 carbon atoms, optionally having a substituent, and optionally having a heteroatom-containing carbon chain,
• wherein m, n, p, s, Y, R1, R2, R3, R4, and R6 are as defined above, W is a protecting group, and Z1 is a halogen atom or a group represented by Formula (3) below,
• wherein * indicates a bond,
• wherein R7, R8, and R13 are as defined above, and Z2 is a halogen atom or a group represented by Formula (3), provided that when Z1 in Formula (7) is a halogen atom, Z2 is a group represented by Formula (3) and that when Z1 in Formula (7) is a group represented by Formula (3), Z2 is a halogen atom,
• wherein m, n, p, s, Y, R1, R2, R3, R4, R6, R7, R8, and R13 are as defined above, and W is a protecting group,
• wherein m, n, p, s, Y, R1, R2, R3, R4, R6, R7, R8, R13, and W are as defined above.

A method for producing a compound of Formula (27) below, the method comprising:

• allowing a compound of Formula (6) below to react with a compound of Formula (24) below to form a compound of Formula (25) below;
• removing groups represented by W from the compound of Formula (25) to form a compound of Formula (26) below;
• and
• obtaining the compound of Formula (27) from the compound of Formula (26),
• wherein m and n are independently 0 or 1, p is an integer of 0 to 4, s is an integer of 0 to 4, Y is an oxygen atom, a sulfur atom, or a divalent group represented by —NR6—, R1 is a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms, R2 is an alkyl group having 1 to 8 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 8 carbon atoms, or a halogen atom, R3 is a linear or branched, saturated or unsaturated, divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, optionally having a substituent, and optionally having a heteroatom-containing carbon chain, R4 is a linear or branched, saturated or unsaturated, monovalent aliphatic hydrocarbon group having 1 to 6 carbon atoms, R6 is a hydrogen atom or a monovalent aliphatic hydrocarbon group, and R7 and R8 are simultaneously hydrogen atoms or combined to form a methylidene group,
• wherein m, n, p, s, Y, R1, R2, R3, R4, and R6 are as defined above, and W is a protecting group,
• wherein W is as defined above, and R14 and R15 are independently a monovalent hydrocarbon group having 1 to 20 carbon atoms,
• wherein m, n, p, s, Y, R1, R2, R3, R4, R6, R7, R8, and W are as defined above,
• wherein m, n, p, s, Y, R1, R2, R3, R4, R6, R7, and R8 are as defined above.