155786-86-0

Basic information

• Product Name: methyl 2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• Synonyms: methyl 2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS NO: 155786-86-0
• Molecular Weight: 897.075
• Mol File: 155786-86-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl 2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside(155786-86-0)
• EPA Substance Registry System: methyl 2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside(155786-86-0)

Safety Data

• Hazardous Substances Data: 155786-86-0(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 7216-73-1 methyl β-D-cellobioside 
• 156038-69-6 methyl 4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 128573-02-4 (1R,2S,3S,4R)-1-amino-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-2,3,4-triol 
• 257936-68-8 methyl O-(6-deoxy-2,3-di-O-pivaloyl-4-O-trifluoromethylsulfonyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 155896-89-2 methyl 4‐O‐(2,3‐di‐O‐benzyl‐4,6‐O‐benzylidene‐β‐D‐glucopyranosyl)‐2,3,6‐tri‐O‐benzyl‐β‐D-glucopyranoside 

Downstream Products

• 423719-29-3 methyl 2,3,6-tri-O-benzyl-4-O-methyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 257936-60-0 methyl O-(2,3-di-O-benzoyl-4-O-chloroacetyl-6-deoxy-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 257936-76-8 methyl O-(4-O-chloroacetyl-6-deoxy-2,3-di-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant articles and documents

Crystal and molecular structure of methyl 4-O-methyl-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside

The cellulose model compound methyl 4-O-methyl-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (6) was synthesised in high overall yield from methyl β-D-cellobioside. The compound was crystallised from methanol to give colourless prisms, and the crystal structure was determined. The monoclinic space group is P21 with Z = 2 and unit cell parameters a = 6.6060 (13), b = 14.074 (3), c = 9.3180 (19) A, β = 108.95(3)°. The structure was solved by direct methods and refined to R = 0.0286 for 2528 reflections. Both glucopyranoses occur in the 4C1 chair conformation with endocyclic bond angles in the range of standard values. The relative orientation of both units described by the interglycosidic torsional angles [φ (O-5′-C-1′-O-4-C-4) -89.1°, φ (C-1′-O-4-C-4-C-5) -152.0°] is responsible for the very flat shape of the molecule and is similar to those found in other cellodextrins. Different rotamers at the exocyclic hydroxymethyl group for both units are present. The hydroxymethyl group of the terminal glucose moiety displays a gauche-trans orientation, whereas the side chain of the reducing unit occurs in a gauche-gauche conformation. The solid state 13C NMR spectrum of compound 6 exhibits all 14 carbon resonances. By using different cross polarisation times, the resonances of the two methyl groups and C-6 carbons can easily be distinguished. Distinct differences of the C-1 and C-4 chemical shifts in the solid and liquid states are found.

Syntheses of all the possible monomethyl ethers and several deoxyhalo analogues of methyl β-lactoside as ligands for the Ricinus communis lecitins

The synthesis of all possible monomethyl ethers of methyl β-lactoside (1) has been performed from 1 in a straightforward way, making use of the different reactivity of the hydroxyl groups in alkylation and stannylation reactions.In addition, the deoxyfluoro derivatives of 1 at positions, 6, 3',4',epi-4', and 6' have been prepared by reaction of the appropriate substrates with diethylaminosulfur trifluoride or tetrabutylammonium fluoride.Finally, the 6-deoxyiodo and 6'-bromodeoxy analogues of 1 have also been prepared.