65370-84-5

Basic information

• Product Name: 1,3,4,6-tetra-O-acetyl-L-gulopyranose
• CAS NO: 65370-84-5
• Molecular Weight: 348.307
• Mol File: 65370-84-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,3,4,6-tetra-O-acetyl-L-gulopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-tetra-O-acetyl-L-gulopyranose(65370-84-5)
• EPA Substance Registry System: 1,3,4,6-tetra-O-acetyl-L-gulopyranose(65370-84-5)

Safety Data

• Hazardous Substances Data: 65370-84-5(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 192753-82-5 2-O-benzyl-3,4,5,6-di-O-isopropyliclenealdehydo-L-gulose 

Downstream Products

• 866529-11-5 1,3,4,6-tetra-O-acetyl-2-O-(2,5-difluorobenzoyl)-β-D-galactopyranose 
• 866529-15-9 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(3,4,6-tri-O-acetyl-2-O-(2,5-difluorobenzoyl)-β-D-galactopyranosyl)-1-thio-β-D-galactopyranozide 
• 866529-12-6 3,4,6-tri-O-acetyl-2-O-(2,5-difluorobenzoyl)-α-D-galactopyranosyl bromide 

Relevant articles and documents

Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars: L-Gulose, L-Idose, and the Disaccharide Subunit of Bleomycin A2

The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation - reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-α-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A2.