One-pot synthesis of alpha/beta-O-glycolipids

Patent metadata

Field	Value
Publication number	US-9586984-B2
Application number	US-201414148477-A
Country	US
Kind code	B2
Filing date	Jan 6, 2014
Priority date	Apr 9, 2007
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

The present invention provides a one-pot method of preparing an unprotected α-O-glycolipid. The first step involves contacting a protected α-iodo sugar with a catalyst and a lipid comprising a hydroxy group, under conditions sufficient to prepare a protected α-O-glycolipid. The second step involves deprotecting the protected α-O-glycolipid under conditions sufficient to prepare the unprotected α-O-glycolipid, wherein the contacting and deprotecting steps are performed in a single vessel. The present invention also provides a one-pot method of preparing an unprotected β-O-glycolipid following the steps for the preparation of the unprotected α-O-glycolipid.

First claim

What is claimed is:

1. A method of preparing an unprotected β-O-glycolipid comprising the steps of:
contacting a protected α-iodo sugar with a catalyst and a lipid comprising a hydroxy group, under conditions sufficient to prepare a protected β-O-glycolipid, wherein the protected α-iodo sugar is selected from the group consisting of:

wherein
each R 1 is independently selected from the group consisting of a trialkylsilyl and a protected saccharide selected from the group consisting of a monosaccharide, a disaccharide, a trisaccharide, an oligosaccharide and a polysaccharide, wherein the protected saccharide is protected with a trialkylsilyl,
the catalyst is selected from the group consisting of silver halide, mercury cyanide, magnesium oxide and silver carbonate, and
the lipid is a ceramide; and

deprotecting the protected β-O-glycolipid under conditions sufficient to prepare the unprotected β-O-glycolipid, wherein the contacting and deprotecting steps are performed in a single vessel.

2. The method of claim 1 , wherein the trialkylsilyl is selected from the group consisting of trimethylsilyl, triethylsilyl, triisopropylsilyl and tert-butyl-dimethylsilyl.

3. The method of claim 1 , wherein the catalyst is silver carbonate.

4. The method of claim 1 , wherein the method of preparing an unprotected β-O-glycolipid is performed using microwave irradiation.

Assignees

• Univ California

Inventors

• Gervay-Hague Jacquelyn
• Du Wenjun
• Kulkarni Suvarn S
• Schombs Matthew

Classifications

• C07H5/06

  Aminosugars · CPC title

• C07J17/005

  Glycosides · CPC title

• C07H15/06

  being a hydroxyalkyl group esterified by a fatty acid · CPC title

• C07H1/00 Primary

  Processes for the preparation of sugar derivatives · CPC title

• C07H15/04

  attached to an oxygen atom of the saccharide radical · CPC title