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

Base Information

• Chemical Name: phenyl 2,3-di-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside
• CAS No.: 864966-90-5
• Molecular Formula: C₁₈H₂₆O₇S
• Molecular Weight: 386.466
• Mol file: 864966-90-5.mol

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

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

There total 1 articles about phenyl 2,3-di-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: 39.0%

(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) + 2,2,3,3-tetramethoxybutane (176798-33-7) → phenyl 2,3-di-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside (864966-90-5) + phenyl 3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-thio-β-D-glucopyranoside (795305-86-1)

Guidance literature:

With (1S)-10-camphorsulfonic acid; trimethyl orthoformate; In methanol; at 65 ℃; for 18h;

DOI:10.1002/ejoc.201300681

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: 45.0%

phenyl 2,3-di-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside (864966-90-5) + benzyl bromide (100-39-0) → C25H32O7S (1280531-36-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 24.5h; Inert atmosphere; Reflux;

DOI:10.1021/ja201024a

upstream raw materials:

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

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

phenyl 4,6-di-O-benzyl-2,3-O-carbonyl-1-thio-β-D-glucopyranoside

methyl 4-O-(4,6-di-O-benzyl-2,3-O-carbonyl-β-D-glucopyranosyl)-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside