186087-99-0

Basic information

• Product Name: diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate
• Synonyms: diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate
• CAS NO: 186087-99-0
• Molecular Weight: 772.832
• Mol File: 186087-99-0.mol

Chemical Properties

• CAS DataBase Reference: diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate(186087-99-0)
• EPA Substance Registry System: diphenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside phosphate(186087-99-0)

Safety Data

• Hazardous Substances Data: 186087-99-0(Hazardous Substances Data)

Upstream product

• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 3458-28-4 D-Mannose 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 

Downstream Products

• 186087-86-5 1-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)formic acid 
• 177696-56-9 1,5-anhydro-2,3,4,6-tetra-O-benzyl-α-D-manno-hexitol 
• 82659-59-4 3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene 
• 116113-70-3 isopropyl-O-2,3,4,6-tetra-O-benzyl-β-D-mannopyranose 
• 116113-69-0 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-isopropoxytetrahydro-2H-pyran 
• 117841-67-5 6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 117841-66-4 6-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 

Relevant articles and documents

Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea

We report highly β-selective bis-thioureas-catalyzed 1,2-cis-O-pyranosylations employing easily accessible acetonide-protected donors. A wide variety of alcohol nucleophiles, including complex natural products, glycosides, and amino acids were β-mannosylated and β-rhamnosylated successfully using an operationally simple protocol under mild and neutral conditions. Less nucleophilic acceptors such as phenols were also glycosylated efficiently in excellent yields and with high β-selectivities.

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.

Direct and stereoselective synthesis of β-D-mannosides using 4,6-O-benzylidene-protected mannosyl diethyl phosphite as a donor

A direct and practical method for the construction of β-mannosidic linkages is described. While β-selectivities in the TMSOTf-promoted glycosidation of 2,3,4,6-tetra-O-benzyl-d-mannosyl diethyl phosphite are found to be highly dependent on the reactivity