74666-83-4

Basic information

• Product Name: ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranoside
• Synonyms: ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranoside
• CAS NO: 74666-83-4
• Molecular Weight: 584.777
• Mol File: 74666-83-4.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranoside(74666-83-4)
• EPA Substance Registry System: ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranoside(74666-83-4)

Safety Data

• Hazardous Substances Data: 74666-83-4(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 75-08-1 ethanethiol 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 3458-28-4 D-Mannose 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 85982-88-3 1-O-trimethylsilyl-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 98-88-4 benzoyl chloride 
• 4132-26-7 2,3,4,6-tetra-O-benzyl 1,5-anhydro-D-arabino-hex-1-enitol 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Downstream Products

• 108739-69-1 methyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 108739-68-0 methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 130847-17-5 2,3,4,6-Tetra-O-benzyl-β-D-Glcp-(1->2)-3-O-benzoyl-4,6-O-benzylidene-α-D-Manp-OMe 
• 130847-15-3 2,3,4,6-Tetra-O-benzyl-α-D-Glcp-(1->2)-3-O-benzoyl-4,6-O-benzylidene-α-D-Manp-OMe 
• 111277-92-0 methyl-2,4-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside 
• 111277-91-9 methyl-2,4-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-L-rhamnopyranoside 
• 127840-78-2 ethyl 2,3,4-tri-O-benzoyl-6-O-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 127840-77-1 ethyl 2,3,4-tri-O-benzoyl-6-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 127840-80-6 ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 117124-67-1 C₅₅H₅₆O₁₂ 
• 203740-95-8 methyl 2-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1→3)-4,6-O-benzylidene-α-D-glucopyranoside 
• 130144-05-7 methyl 2-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→3)-4,6-O-benzylidene-α-D-glucopyranoside 
• 108678-06-4 (3aS,4R,6R,7R,7aS)-6-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-7-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 108678-07-5 (3aS,4R,6R,7R,7aS)-6-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-7-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran 

Relevant articles and documents

Anomeric Thioglycosides Give Different Anomeric Product Distributions under NIS/TfOH Activation

The reaction of a series of anomeric thioglycosides with various glycosyl acceptors and N-iodosuccinimide/catalytic triflic acid was investigated with respect to reactivity and anomeric selectivity. In general, β-configured donors were found to give a more β-selective reaction outcome compared to their α-configured counterparts. The relative reactivity of various thioglycosides was measured through competition experiments, and the following order was established: phenyl, tolyl, methyl, ethyl, isopropyl, and 1-adamantyl.

Regio- and stereoselective glycosylation of 2-(o-dihydroxyborylbenzyl) thioglucoside and unprotected methyl glycosides

A highly regio- and stereoselective glycosylation of a boronic acid-containing thioglucoside and unprotected methyl glycosides is described. A boronic acid moiety was installed at the ortho-position of the 2-O-benzyl group of a thioglucosyl donor. This provides transient partial protection for the unprotected glycosyl acceptor upon condensation and concomitantly prearranged the acceptor with respect to the donor for the ensuing intramolecular glycosylation.

An Empirical Understanding of the Glycosylation Reaction

Reliable glycosylation reactions that allow for the stereo- and regioselective installation of glycosidic linkages are paramount to the chemical synthesis of glycan chains. The stereoselectivity of glycosylations is exceedingly difficult to control due to the reaction's high degree of sensitivity and its shifting, simultaneous mechanistic pathways that are controlled by variables of unknown degree of influence, dominance, or interdependency. An automated platform was devised to quickly, reproducibly, and systematically screen glycosylations and thereby address this fundamental problem. Thirteen variables were investigated in as isolated a manner as possible, to identify and quantify inherent preferences of electrophilic glycosylating agents (glycosyl donors) and nucleophiles (glycosyl acceptors). Ways to enhance, suppress, or even override these preferences using judicious environmental conditions were discovered. Glycosylations involving two specific partners can be tuned to produce either 11:1 selectivity of one stereoisomer or 9:1 of the other by merely changing the reaction conditions.