241471-10-3

Basic information

• Product Name: ethyl 2-O-benzyl-4,6-O-benzylidene-6-O-(3-bromomethylbenzyl)-1-thio-β-D-glucopyranoside
• Synonyms: ethyl 2-O-benzyl-4,6-O-benzylidene-6-O-(3-bromomethylbenzyl)-1-thio-β-D-glucopyranoside
• CAS NO: 241471-10-3
• Molecular Weight: 585.559
• Mol File: 241471-10-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: ethyl 2-O-benzyl-4,6-O-benzylidene-6-O-(3-bromomethylbenzyl)-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-O-benzyl-4,6-O-benzylidene-6-O-(3-bromomethylbenzyl)-1-thio-β-D-glucopyranoside(241471-10-3)
• EPA Substance Registry System: ethyl 2-O-benzyl-4,6-O-benzylidene-6-O-(3-bromomethylbenzyl)-1-thio-β-D-glucopyranoside(241471-10-3)

Safety Data

• Hazardous Substances Data: 241471-10-3(Hazardous Substances Data)

Upstream product

• 174172-99-7 ethyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside 
• 626-15-3 1,3-bis-(bromomethyl)benzene 

Downstream Products

• 744-05-8 methyl α-D-glucopyranosyl-(1->4)-α-D-glucopyranoside 
• 241471-12-5 methyl 6,3'-O-(1,3-xylylene)-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1'->4)-2,3-di-O-benzyl-α-D-glucopyranoside 
• 241471-11-4 ethyl 3-O-[3-(methyl 2,3-di-O-benzyl-α-D-glucopyranoside-6-yloxymethyl)-benzyl]-2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 

Relevant articles and documents

Efficient Intramolecular Glycosylation Supported by a Rigid Spacer

The m-xylylene moiety was employed as rigid spacer in intramolecular glycoside bond formation. Fifteen-membered macrocycle formation starting from 6-O-linked donor and 6- and 4-O-linked acceptor (5a,b, 6b) led exclusively to β(1-4)- and β(1-6)-linked compounds 7β and 8β, respectively, which gave cellobioside and gentiobioside derivatives. The glycosylation yields could be improved by 14-membered macrocycle formation. In the four cases studied, the donor was 6-O-linked to the spacer. For the acceptor linkage to the spacer and the accepting hydroxy group, relative D-/L-threo- and D-/L-erythro-arrangements were chosen. Standard glycosylation conditions led in three cases (13, 14, 23) only to β-linkage in high yield (16β, 17β, 25β). For the transformation of 24, having a D-erythro-arrangement in the acceptor moiety, the α-anomer 26α was preferentially obtained. Limitation of the conformational space of the donor and the acceptor as in 31, which is stereochemically identical with 24, led to the corresponding α-glycoside 32α in 87% yield. Synthesis of a pseudo mirror image of 23 [having 6-(D)/3-(D-threo)-arrangement], namely 35, having 3(L)/6-(L-threo)-arrangement of the donor and acceptor moieties, expectedly gave only α-glycoside 36α in very high yield. Thus, the efficiency and versatility of this conceptual approach to intramolecular glycoside bond formation is exhibited.