869639-08-7

Basic information

• Product Name: ethyl 6-O-benzoyl-3,4-di-O-benzyl-1-thio-β-D-glucopyranoside
• Synonyms: ethyl 6-O-benzoyl-3,4-di-O-benzyl-1-thio-β-D-glucopyranoside
• CAS NO: 869639-08-7
• Molecular Weight: 508.635
• Mol File: 869639-08-7.mol

Chemical Properties

• CAS DataBase Reference: ethyl 6-O-benzoyl-3,4-di-O-benzyl-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 6-O-benzoyl-3,4-di-O-benzyl-1-thio-β-D-glucopyranoside(869639-08-7)
• EPA Substance Registry System: ethyl 6-O-benzoyl-3,4-di-O-benzyl-1-thio-β-D-glucopyranoside(869639-08-7)

Safety Data

• Hazardous Substances Data: 869639-08-7(Hazardous Substances Data)

Upstream product

• 1223406-28-7 ethyl 3,4-di-O-benzyl-6-O-benzoyl-2-O-(2-nitro)phenylacetyl-1-thio-β-D-glucopyranoside 
• 146608-95-9 ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 869639-07-6 ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-methoxymethyl-1-thio-β-D-glucopyranoside 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 

Downstream Products

• 869639-06-5 methyl O-(6-O-benzoyl-3,4-di-O-benzyl-2-O-phenylcarbamoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 869639-01-0 ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-phenylcarbamoyl-1-thio-β-D-glucopyranoside 

Relevant articles and documents

(2-Nitrophenyl)acetyl: A new, selectively removable hydroxyl protecting group

Figure presented The utility of the (2-nitrophenyl)acetyl (NPAc) group for the protection of hydroxyl functions is reported. (2-Nitrophenyl)acetates are readily prepared starting from the commercially available, inexpensive (2-nitrophenyl)acetic acid, and these esters are stable under a series of common carbohydrate transformations. The NPAc group can be removed selectively using Zn and NH4Cl without affecting a series of common protecting groups. This new protecting group is orthogonal with the commonly used tert-butyldimethylsilyl, levulinoyl, 9-fluorenylmethoxycarbonyl, naphthylmethyl, and p-methoxybenzyl groups.

Convenient construction of a variety of glycosidic linkages using a universal glucosyl donor

This letter deals with the concept of constructing four types (cis-α, trans-α, cis-β, and trans-β) of glycosidic linkages using a universal glucosyl donor. The selectively protected universal glucosyl donor 8 was synthesized in 36% yield from d-glucose (eight steps). The donor 8 undergoes glycosidation with a primary carbohydrate alcohol 7 to give disaccharide 9 having a 1,2-cis-α-glycosidic linkage in 90% yield. The construction of the corresponding 1,2-trans-α-glycosidic linkage was performed in 68% yield (three steps) from 9. A similar glycosidation of the 2-O-(N- phenylcarbamoyl)-glucosyl donor 6 derived from 8 with 7 gave disaccharide 11 having a 1,2-trans-β-glycosidic linkage in 75% yield. The construction of the corresponding 1,2-cis-β-linkage was performed in 53% yield (three steps) from 11.