151123-94-3

Basic information

• Product Name: Ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-1-thio-α-D-glucopyranoside
• Synonyms: Ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-1-thio-α-D-glucopyranoside
• CAS NO: 151123-94-3
• Molecular Weight: 492.977
• Mol File: 151123-94-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-1-thio-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-1-thio-α-D-glucopyranoside(151123-94-3)
• EPA Substance Registry System: Ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-1-thio-α-D-glucopyranoside(151123-94-3)

Safety Data

• Hazardous Substances Data: 151123-94-3(Hazardous Substances Data)

Upstream product

• 604-69-3 β-D-glucose pentaacetate 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 7473-36-1 (2R,3R,4S,5S,6R)-2-Ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 151123-92-1 Ethyl 4,6-O-benzylidene-1-thio-α-D-glucopyranoside 
• 79-04-9 chloroacetyl chloride 
• 151123-93-2 Ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-glucopyranoside 

Downstream Products

• 151072-62-7 Methyl O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 151072-63-8 Methyl O-(2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 151072-58-1 Ethyl O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-glucopyranoside 
• 151072-60-5 Methyl O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 151072-59-2 O-(2-O-Benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl chloride 
• 151072-61-6 Methyl O-(2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 151072-57-0 Methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-glucopyranoside 
• 38992-99-3 methyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 473545-19-6 ethyl 2-O-benzoyl-4-O-benzyl-1-thio-α-D-glucopyranoside 
• 162316-88-3 Ethyl 2-O-benzoyl-4-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-α-D-glucopyranoside 
• 625388-43-4 ethyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-1-thio-α-D-glucopyranoside 
• 151072-56-9 2-O-Benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-glucopyranosyl chloride 

Relevant articles and documents

Synthesis of the laminara-oligosaccharide methyl β-glycosides of dp 3-8

Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside has been prepared in a good yield by anomerization of the corresponding β-thioglucoside with tin(IV) chloride and transformed, in three steps, into ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-α-D-glucopyranoside (18). Chloroacetylation of 18, followed by treatment of the product with chlorine gave crystalline 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-glucopyranosyl chloride (20). This was coupled with methanol in the presence of silver carbonate-silver perchlorate and the product was O-dechloroacetylated to afford methyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside (22). Silver triflate-promoted glucosylation of 18 with 20 gave a β-(1 → 3)-linked disaccharide derivative, reaction of which with chlorine yielded crystalline O-(2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-glucopyranosyl) -(1 → 3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl chloride (24). Likewise, condensation of 22 with 20 gave a β-(1 → 3)linked disaccharide glycoside, which was partially deprotected to give methyl O-(2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1 → 3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside (26). The methyl β-glycosides of a homologous series of (1 → 3)-linked β-D-gluco-oligosaccharides from the tri- to the octa-saccharide have been synthesized in a blockwise manner by using 22 and 26 as the glycosyl acceptors, 24 as the disaccharide donor, and silver triflate as the promoter. Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyrano- side has been prepared in a good yield by anomerization of the corresponding B-thioglucoside with tin(IV) chloride and transformed, in three steps.