Ethyl 2,3,6-tri-O-benzyl-1-thio-b-D-glucopyranoside

Base Information

• Chemical Name: Ethyl 2,3,6-tri-O-benzyl-1-thio-b-D-glucopyranoside
• CAS No.: 141263-02-7
• Molecular Formula: C29H34 O5 S
• Molecular Weight: 494.652
• Mol file: 141263-02-7.mol

Synonyms:Ethyl 2,3,6-tri-O-benzyl-1-thio-b-D-glucopyranoside;ETHYL 2,3,6-TRI-O-BENZYL-1-THIO-β-D-GLUCOPYRANOSIDE

Chemical Property of Ethyl 2,3,6-tri-O-benzyl-1-thio-b-D-glucopyranoside

Chemical Property:

• PSA: 82.45000
• LogP: 5.21290

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 2,3,6-tri-O-benzyl-b-D-thioglucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ethyl 2,3,6-tri-O-benzyl-1-thio-b-D-glucopyranoside

There total 10 articles about Ethyl 2,3,6-tri-O-benzyl-1-thio-b-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: 99.0%

ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside (1415590-57-6) → ethyl 2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (141263-02-7)

Guidance literature:

With copper diacetate; In methanol; dichloromethane; at 20 ℃; for 1.5h; Reagent/catalyst; Solvent; chemoselective reaction; Catalytic behavior; Inert atmosphere;

DOI:10.1039/d0ob00803f

Reference yield: 72.0%

ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (197853-41-1) → ethyl 2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (141263-02-7)

Guidance literature:

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; for 0.166667h; Ambient temperature;

Reference yield: 46.0%

benzyl bromide (100-39-0) + ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside (152964-70-0) → ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside (39483-51-7,119645-03-3,128850-50-0,126461-54-9) + ethyl 2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (141263-02-7)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; for 80h; Heating;

upstream raw materials:

benzyl bromide

ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside

Ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Downstream raw materials:

ethyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

ethyl 2,3,6-tri-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-glucopyranoside

Refernces

• 1、 Garegg, Per J.,Kvarnstroem, Ingemar,Niklasson, Annika,Niklasson, Gunilla,Svensson, Stefan C. T.. "PARTIAL SUBSTITUTION OF THIOGLYCOSIDES BY PHASE TRANSFER CATALYZED BENZOYLATION AND BENZYLATION". . p. 933 - 954. Retrieved 2007/10/02.