90358-03-5

Basic information

• Product Name: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl di-n-butyl phosphate
• Synonyms: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl di-n-butyl phosphate
• CAS NO: 90358-03-5
• Molecular Weight: 732.851
• Mol File: 90358-03-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl di-n-butyl phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl di-n-butyl phosphate(90358-03-5)
• EPA Substance Registry System: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl di-n-butyl phosphate(90358-03-5)

Safety Data

• Hazardous Substances Data: 90358-03-5(Hazardous Substances Data)

Upstream product

• 56245-60-4 ethyl 1-thio-β-D-galactopyranoside 
• 55722-49-1 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 125411-99-6 ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 107-66-4 dibutyl phosphate 
• 90358-01-3 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate 

Downstream Products

• 136984-92-4 1-O-isopropyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranose 
• 136984-89-9 1-O-isopropyl-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose 
• 1430237-43-6 C₉₃H₁₀₂Cl₃NO₁₈Si 

Relevant articles and documents

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.