phenyl 4,6-di-O-benzyl-2,3-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 4,6-di-O-benzyl-2,3-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-1-thio-β-D-glucopyranoside
• CAS No.: 864966-91-6
• Molecular Formula: C₃₂H₃₈O₇S
• Molecular Weight: 566.716
• Mol file: 864966-91-6.mol

Synonyms:phenyl 4,6-di-O-benzyl-2,3-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 4,6-di-O-benzyl-2,3-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4,6-di-O-benzyl-2,3-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-1-thio-β-D-glucopyranoside

There total 4 articles about phenyl 4,6-di-O-benzyl-2,3-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-1-thio-β-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: 98.0%

phenyl 2,3-di-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside (864966-90-5) + benzyl bromide (100-39-0) → phenyl 4,6-di-O-benzyl-2,3-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-1-thio-β-D-glucopyranoside (864966-91-6)

Guidance literature:

phenyl 2,3-di-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; for 0.166667h; cooling;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

DOI:10.1021/jo0508999

Reference yield: 84.0%

phenyl 4,6-di-O-benzyl-1-thio-β-D-glucopyranoside (864966-92-7) + dimethylglyoxal (431-03-8) + trimethyl orthoformate (149-73-5) → phenyl 4,6-di-O-benzyl-2,3-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-1-thio-β-D-glucopyranoside (864966-91-6)

Guidance literature:

With boron trifluoride diethyl etherate; In methanol; at 20 ℃; for 42h; Inert atmosphere;

DOI:10.1002/ejoc.201700671

Reference yield:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) → phenyl 4,6-di-O-benzyl-2,3-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-1-thio-β-D-glucopyranoside (864966-91-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trimethyl orthoformate; camphorsulfonic acid / methanol / 18 h / Heating

2.1: sodium hydride / dimethylformamide / 0.17 h / cooling

2.2: 98 percent / dimethylformamide / 6 h / 20 °C

With camphor-10-sulfonic acid; sodium hydride; trimethyl orthoformate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo0508999

upstream raw materials:

phenyl 2,3-di-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside

benzyl bromide

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

2,2,3,3-tetramethoxybutane

Downstream raw materials:

phenyl 4,6-di-O-benzyl-1-thio-β-D-glucopyranoside

3β-cholestanyl 4,6-di-O-benzyl-2,3-O-carbonyl-β-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(4,6-di-O-benzyl-2,3-O-carbonyl-β-D-glucopyranosyl)-(1->4)-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-(4,6-di-O-benzyl-2,3-O-carbonyl-β-D-glucopyranosyl)-(1->6)-α-D-glucopyranoside