4356-80-3

Basic information

• Product Name: methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS NO: 4356-80-3
• Molecular Weight: 464.558
• Mol File: 4356-80-3.mol
• Article Data: 38

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside(4356-80-3)
• EPA Substance Registry System: methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside(4356-80-3)

Safety Data

• Hazardous Substances Data: 4356-80-3(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 6988-40-5 methyl 2,3-di-O-benzyl-β-D-glucopyranoside 
• 101312-02-1 methyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside 
• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 13035-24-0 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 29600-81-5 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside 
• 7177-79-9 (2R,4aR,6S,7R,8S,8aS)-7,8-Bis-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 100-39-0 benzyl bromide 
• 3396-99-4 methyl α-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 64552-06-3 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-(S)-benzylidene-α-D-galactopyranoside 
• 1206803-23-7 methyl 2,3,4-tri-O-benzyl-6-O-triethyl-silyl-α-D-galactopyranoside 
• 18311-26-7 methyl 6-O-triphenylmethyl-α-D-galactopyranoside 

Downstream Products

• 116096-63-0 methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 
• 116113-10-1 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 4356-79-0 methyl 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 128745-97-1 methyl 2,3,4-tri-O-acetyl-β-D-xylopyranosyl(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 170639-48-2 (1R,2S,3S,4R,5S)-2,3,4-Tris-benzyloxy-5-hydroxymethyl-cyclopentanol 
• 639504-92-0 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-β-D-glucopyranoside 
• 354797-81-2 methyl 6-O-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 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 
• 228106-20-5 Acetic acid 4-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethyl)-phenyl ester 
• 230620-32-3 (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl (N,N-diisopropyl) phosphoramidite 
• 244286-92-8 methyl 2,3,4-tri-O-benzyl-6-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 64363-77-5 methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside 
• 129796-72-1 methyl O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 

Relevant articles and documents

Addressing the biochemical foundations of a glucose-based "trojan horse"-strategy to boron neutron capture therapy: From chemical synthesis to in vitro assessment

Boron neutron capture therapy (BNCT) for cancer is on the rise worldwide due to recent developments of in-hospital neutron accelerators which are expected to revolutionize patient treatments. There is an urgent need for improved boron delivery agents, and herein we have focused on studying the biochemical foundations upon which a successful GLUT1-targeting strategy to BNCT could be based. By combining synthesis and molecular modeling with affinity and cytotoxicity studies, we unravel the mechanisms behind the considerable potential of appropriately designed glucoconjugates as boron delivery agents for BNCT. In addition to addressing the biochemical premises of the approach in detail, we report on a hit glucoconjugate which displays good cytocompatibility, aqueous solubility, high transporter affinity, and, crucially, an exceptional boron delivery capacity in the in vitro assessment thereby pointing toward the significant potential embedded in this approach.

Chiron approach to the total synthesis of Amaryllidaceae alkaloid (+)-lycoricidine

A highly stereoselective total synthesis of Amaryllidaceae alkaloid starting from α-D-galactopyranoside has been described. The salient features of this total synthesis are Ferrier carbocyclization reaction for the synthesis of ring A and Suzuki Miyaura c

Stable analogues of nojirimycin-synthesis and biological evaluation of nojiristegine and manno-nojiristegine

Two novel iminosugars called nojiristegines, being structural hybrids between nor-tropane alkaloid calystegine and nojirimycins, have been synthesised and found to be stable molecules despite the presence of a hemiaminal functionality. The synthesised iminosugars were evaluated against a panel of glycosidases and the best inhibition (IC50), found against α-glucosidases, was in the micromolar region. The compounds were also evaluated as potential antibiotics but no useful level of activity was observed.