Process for production of ascarylose and related compounds
AssigneeAscribe Bioscience Inc.
InventorJames Eagan
Life of this patent
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Abstract
This application relates to efficient methods for the synthesis of ascarylose and its derivatives. A method for the production of ascarylose includes: providing, as a feedstock, a 1-O-substituted rhamnose; forming a mono-sulfonate ester at the 3-OH group of the 1-O-substituted rhamnose; and treating the mono-sulfonate ester with a hydride source to form a 1-O-substituted ascarylose. Forming the mono-sulfonate ester can advantageously be conducted on a 1-O-substituted rhamnose without hydroxyl protecting groups at either the 2-OH or 4-OH-positions.
Claims29
A method for the production of 1-O-substituted ascarylose, comprising:
- providing as a feedstock a 1-O-substituted rhamnose having the structure of Formula II, wherein Z is a non-hydrogen substituent;
- forming a mono-sulfonate ester at the 3-OH group of the feedstock;
- and
- treating the mono-sulfonate ester with a hydride source to form the 1-O-substituted ascarylose,
- wherein forming the mono-sulfonate ester is conducted on the 1-O-substituted rhamnose without hydroxyl protecting groups at either the 2-OH or 4-OH-positions.
A method for the production of 1-O-substituted ascarylose, comprising:
- providing, as a feedstock, the 3-sulfonate ester of a 1-O-substituted rhamnose derivative having the structure of Formula IV, wherein Z is a non-hydrogen substituent and Q is an optionally substituted aliphatic or aromatic moiety:
- and
- treating the mono-sulfonate ester with a strong base and a hydride source to form the 1-O-substituted ascarylose.
Dependencies are inferred from the claim text.