ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(3-bromobenzyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(3-bromobenzyl)-1-thio-β-D-glucopyranoside
• CAS No.: 522632-95-7
• Molecular Formula: C₂₉H₃₁BrO₅S
• Molecular Weight: 571.532
• Mol file: 522632-95-7.mol

Synonyms:ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(3-bromobenzyl)-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(3-bromobenzyl)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(3-bromobenzyl)-1-thio-β-D-glucopyranoside

There total 1 articles about ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(3-bromobenzyl)-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: 90.0%

meta-bromobenzyl bromide (823-78-9) + ethyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside (174172-99-7) → ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(3-bromobenzyl)-1-thio-β-D-glucopyranoside (522632-95-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

Reference yield:

Diisopropylsilyl dichloride (7751-38-4) + ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(3-bromobenzyl)-1-thio-β-D-glucopyranoside (522632-95-7) → ethyl 2-O-benzyl-4,5-O-benzylidene-3-O-[3-(chlorodiisopropylsilyl)benzyl]-1-thio-β-D-glucopyranoside (522632-96-8)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; hexane; at -100 - -50 ℃; for 1h;

DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

Reference yield:

ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-(3-bromobenzyl)-1-thio-β-D-glucopyranoside (522632-95-7) → methyl 6,3'-O-[3-(diisopropylsilyl)benzyl]-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside (522632-99-1)

Guidance literature:

Multi-step reaction with 4 steps

1: tBuLi / tetrahydrofuran; hexane / 1 h / -100 - -50 °C

2: 2.01 g / NaH / dimethylformamide / 20 h

3: 87 percent / DDQ / CH₂Cl₂; H₂O / 20 h / 20 °C

4: 45 percent / NIS; trifluoromethanesulfonic acid / 0.5 h / 20 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; tert.-butyl lithium; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200301)2003:1<128::AID-EJOC128>3.0.CO;2-S

upstream raw materials:

meta-bromobenzyl bromide

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

Downstream raw materials:

ethyl 2-O-benzyl-4,5-O-benzylidene-3-O-[3-(chlorodiisopropylsilyl)benzyl]-1-thio-β-D-glucopyranoside

methyl 6,3'-O-[3-(diisopropylsilyl)benzyl]-(2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside

methyl 6,3'-O-[3-(diisopropylsilyl)benzyl]-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside

ethyl 2-O-benzyl-4,6-O-benzylidene-3-O-{3-[methyl 2,3-di-O-benzyl-α-D-glucopyranosid-6-yloxy]diisopropylsilylbenzyl}-1-thio-β-D-glucopyranoside