67525-69-3

Basic information

• Product Name: tert-butyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• CAS NO: 67525-69-3
• Molecular Weight: 596.764
• Mol File: 67525-69-3.mol
• Article Data: 31

Chemical Properties

• CAS DataBase Reference: tert-butyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside(67525-69-3)
• EPA Substance Registry System: tert-butyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside(67525-69-3)

Safety Data

• Hazardous Substances Data: 67525-69-3(Hazardous Substances Data)

Upstream product

• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 507-19-7 t-butyl bromide 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 75-65-0 tert-butyl alcohol 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 132201-75-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 56822-49-2 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 

Downstream Products

• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 

Relevant articles and documents

Zn- And Cu-catalyzed coupling of tertiary alkyl bromides and oxalates to forge challenging C?O, C?S, and C?N bonds

We describe here the facile construction of sterically hindered tertiary alkyl ethers and thioethers via the Zn(OTf)2catalyzed coupling of alcohols/phenols with unactivated tertiary alkyl bromides and the Cu(OTf)2-catalyzed thiolation of unactivated tertiary alkyl oxalates with thiols. The present protocol represents one of the most effective unactivated tertiary C(sp3)? heteroatom bond-forming conditions via readily accessible Lewis acid catalysis that is surprisingly less developed.

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.

The tertiary-butyl group: Selective protection of the anomeric centre and evaluation of its orthogonal cleavage

The tertiary-butyl group has not been examined extensively as a protecting group. In this work, we describe the synthesis of tert-butyl glycosides via the Fischer glycosylation protocol. Furthermore, its utility as a temporary anomeric protecting group was evaluated. A range of differentially protected monosaccharides was used to investigate the stability of the tert-butyl group upon the introduction of other protecting groups; and compatibility of its cleavage in the presence of the latter.