Methyl2,3-di-O-methyl-6-O-(phenylmethyl)-a-D-glucopyranoside

Base Information

• Chemical Name: Methyl2,3-di-O-methyl-6-O-(phenylmethyl)-a-D-glucopyranoside
• CAS No.: 106220-89-7
• Molecular Formula: C16H24 O6
• Molecular Weight: 312.363
• Hs Code.: 2932999099
• Mol file: 106220-89-7.mol

Synonyms:Methyl2,3-di-O-methyl-6-O-(phenylmethyl)-a-D-glucopyranoside

Chemical Property of Methyl2,3-di-O-methyl-6-O-(phenylmethyl)-a-D-glucopyranoside

Chemical Property:

• PSA: 66.38000
• LogP: 0.96540

Purity/Quality:

98%, ^*data from raw suppliers

Methyl 6-O-benzyl-2,3-di-O-methyl-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl2,3-di-O-methyl-6-O-(phenylmethyl)-a-D-glucopyranoside

There total 8 articles about Methyl2,3-di-O-methyl-6-O-(phenylmethyl)-a-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside (3013-58-9,3051-89-6,4261-46-5,6748-99-8,13035-20-6,13502-46-0,22893-88-5,35311-32-1,53767-28-5,56586-53-9,56586-54-0,69744-11-2,94480-09-8,120200-48-8,120200-49-9,120200-50-2,120200-52-4) → methyl 6-O-benzyl-2,3-di-O-methyl-α-D-glucopyranoside (106220-89-7)

Guidance literature:

methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside; With sodium cyanoborohydride; In acetonitrile; for 0.0833333h; Molecular sieve;

With iodine; In acetonitrile; for 0.333333h; regiospecific reaction; Molecular sieve;

DOI:10.1016/j.carres.2010.10.013

Reference yield: 93.0%

methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside (3013-58-9,3051-89-6,4261-46-5,6748-99-8,13035-20-6,13502-46-0,22893-88-5,35311-32-1,53767-28-5,56586-53-9,56586-54-0,69744-11-2,94480-09-8,120200-48-8,120200-49-9,120200-50-2,120200-52-4) → methyl 6-O-benzyl-2,3-di-O-methyl-α-D-glucopyranoside (106220-89-7)

Guidance literature:

With aluminium trichloride; triethylamine-borone; In tetrahydrofuran; for 7h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90570-8

Reference yield: 78.0%

(3R,4S,5R,6S)-4,5,6-Trimethoxy-2-(2-phenyl-benzo[1,3]dithiol-2-yloxymethyl)-tetrahydro-pyran-3-ol (130132-26-2) → methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside (3013-58-9,3051-89-6,4261-46-5,6748-99-8,13035-20-6,13502-46-0,22893-88-5,35311-32-1,53767-28-5,56586-53-9,56586-54-0,69744-11-2,94480-09-8,120200-48-8,120200-49-9,120200-50-2,120200-52-4) + methyl 6-O-benzyl-2,3-di-O-methyl-α-D-glucopyranoside (106220-89-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In benzene; Heating;

DOI:10.1016/S0040-4039(00)89023-1

upstream raw materials:

methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside

(3R,4S,5R,6S)-4,5,6-Trimethoxy-2-(2-phenyl-benzo[1,3]dithiol-2-yloxymethyl)-tetrahydro-pyran-3-ol

methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside

methyl 4,6-O-benzylidene-α-D-glucopyranoside

Downstream raw materials:

((2R,3R,4R,5R,6S)-2-Benzyloxymethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

methyl 2,3-di-O-methyl-4-O-p-methoxybenzyl-α-D-glucopyranoside

Refernces

• 1、 Hajko, Janos,Szabovik, Gabriella,Kerekgyarto, Janos,Kajtar, Marton,Liptak, Andras. "Hydrogenolysis of the 4,6-o-ketals of glucopyranosides. Configuration-dependent high regio- and stereo-selectivity of the diastereoisomeric acetophenone derivatives". . p. 357 - 363. Retrieved 2007/10/03.
• 2、 Zeller, Samuel G.,D'Ambra, Anello J.,Rice, Michael J.,Gray, Gary R.. "SYNTHESIS AND MASS SPECTRA OF 4-O-ACETYL-1,5-ANHYDRO-2,3,6-TRI-O-ETHYL-D-GLUCITOL AND THE POSITIONAL ISOMER OF 4-O-ACETYL-1,5-ANHYDRO-DI-O-ETHYL-O-METHYL-D-GLUCITOL AND 4-O-ACETYL-1,5-ANHYDRO-O-ETHYL-DI-O-METHYL-D-GLUCITOL". . p. 53 - 62. Retrieved 2007/10/02.