Glycolipid derivative

A method for preparing a compound having the formula (d),

• wherein
• R0 represents —OH, —NH2, —NHAc,
• X is a saturated or an unsaturated carbon chain of carbon number 11 to 25 which can contain a hydroxyl group,
• Z represents —CO—, —SO2—, and
• W is a saturated or an unsaturated carbon chain from 9 to 17 which can contain a hydroxyl group, comprising the steps of:
• reacting a compound of formula (a) in a Wittig reaction
• wherein
• R1 represents —O—R4, —O—Si(R4)3, —O—CO—R4;
• R5 represents —O—R4, —O—Si(R4)3, —O—CO—R4, —NAc2, —NHAc;
• R3 represents —PPh3+I−, —P(═O)—(O—R4)2 wherein
• R4 represents lower alkyl or phenyl group;
• b denotes an integer of 0-5, with a compound of formula (b),
• wherein
• R2 represents —O—R4, —O—Si(R4)3, —O—CO—R4,
• wherein R4 represents lower alkyl or phenyl group;
• in the presence of a base to produce a compound of the following formula (c),
• and deprotecting the compound of formula (c) to produce the compound of formula (d).

A method for preparing a compound having the formula (e),

• wherein
• X1 is a saturated or an unsaturated carbon chain of carbon number 11 to 25 which can contain a hydroxyl group;
• W2 is a saturated or an unsaturated carbon chain from 9 to 17 which can contain a hydroxyl group;
• R0 represents —OH, —NH2, —NHAc,
• Z represents —CO—, —SO2—, and
• b denotes an integer of 0-5, comprising the steps of:
• hydrogenating the compound of formula (g),
• wherein
• R1 represents —O—R4, —O—Si(R4)3, —O—CO—R4;
• R2 represents —O—R4, —O—Si(R4)3, —O—CO—R4;
• wherein
• R4 represents lower alkyl or phenyl group,
• R5 represents —O—R4, —O—Si(R4)3, —O—CO—R4, —NAc2, —NHAc;
• W is a saturated or an unsaturated carbon chain from 9 to 17 which can contain a hydroxyl group,
• b denotes an integer of 0-5,
• Boc represents t-butyloxy carbonyl group, with a palladium catalyst Pd/c or Pd(OH)2
• deprotecting the Boc group followed by amidation or sulfonylation to produce the compound of formula (e).

A method for preparing a compound having the formula (k),

• wherein
• R0 represents —OH, —NH2, —NHAc,
• X is a saturated or an unsaturated carbon chain of carbon number 11 to 25 which can contain a hydroxyl group,
• Z represents —CO—, —SO2—, and
• W is a saturated or an unsaturated carbon chain from 9 to 17 which can contain a hydroxyl group,
• comprising the step of glycosylating a compound of formula (h),
• wherein
• R1 represents —O—R4, —O—Si(R4)3, —O—CO—R4;
• R5 represents —O—R4, —O—Si(R4)3, —O—CO—R4, —NAc2, —NHAc;
• A represents —SH or —NH2, with a compound of formula (i),
• wherein
• R2 represents —O—R4, —O—Si(R4)3, —O—CO—R4;
• wherein
• R4 represents lower alkyl or phenyl group;
• B represents a leaving group selected from the group consisting of methanesulfonyloxy group and halogens;
• Boc represents t-butyloxycarbonyl group, to produce a compound of formula (j),
• wherein
• Q represents —S— or —NH—,
• deprotecting the Boc group followed by amidation or sulfonylation, and further deprotection, to produce the compound of formula (k).

A method for preparing a compound having the formula (m),

• wherein
• R0 represents —OH, —NH2, —NHAc,
• X is a saturated or an unsaturated carbon chain of carbon number 11 to 25 which can contain a hydroxyl group,
• Y represents —(CH2)a—CH═CH—(CH2)a′—, —(CH2)a—, —S(O)0-2CH2—, —NHCH2—, wherein a and a′ each denote an integer of 0-5 and a+a′ is 5 or under;
• Z represents —CO—, —SO2—,
• W is a saturated or an unsaturated carbon chain from 9 to 17 which can contain a hydroxyl group;
• R6 represents —CO2H, —CH2OCH2CO2H, —CH2OSO3H, comprising carrying out 2,2,6,6,-tetramethyl-1-piperidinyloxyradical oxidation (TEMPO oxidation), sulfonylation, or carboxymethylation with a compound of formula (l),
• to produce the compound of formula (m).

An immunostimulating agent containing the compound of general formula (I)

• wherein
• W is a saturated or an unsaturated carbon chain from 9 to 17 which can contain a hydroxyl group;
• X is a saturated or an unsaturated carbon chain of carbon number 11 to 25 which can contain a hydroxyl group;
• Y represents —(CH2)a—CH═CH—(CH2)a′—, —(CH2)a—, —S(O)0-2CH2—, —NHCH2—, wherein a and a′ each denote an integer of 0-5 and a+a′ is 5 or under;
• Z represents —CO—, —SO2—;
• R represents —CH2OH, —CO2H, —CH2OCH2CO2H, —CH2OSO3H;
• and
• R0 represents —OH, —NH2, —NHAc;
• and/or the pharmaceutically acceptable salt as an effective ingredient.