ethyl 4-O-allyl-2-O-benzyl-6-O-triisopropylsilyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 4-O-allyl-2-O-benzyl-6-O-triisopropylsilyl-1-thio-β-D-glucopyranoside
• CAS No.: 356047-05-7
• Molecular Formula: C₂₇H₄₆O₅SSi
• Molecular Weight: 510.811
• Mol file: 356047-05-7.mol

Synonyms:ethyl 4-O-allyl-2-O-benzyl-6-O-triisopropylsilyl-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 4-O-allyl-2-O-benzyl-6-O-triisopropylsilyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4-O-allyl-2-O-benzyl-6-O-triisopropylsilyl-1-thio-β-D-glucopyranoside

There total 6 articles about ethyl 4-O-allyl-2-O-benzyl-6-O-triisopropylsilyl-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: 95.0%

ethyl 4-O-allyl-2-O-benzyl-3-O-(4-methoxybenzyl)-6-O-triisopropylsilyl-1-thio-β-D-glucopyranoside (356047-03-5) → ethyl 4-O-allyl-2-O-benzyl-6-O-triisopropylsilyl-1-thio-β-D-glucopyranoside (356047-05-7)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 5h;

DOI:10.1002/1099-0690(200106)2001:11<2055::AID-EJOC2055>3.0.CO;2-N

Reference yield:

triisopropylsilyl chloride (13154-24-0) → ethyl 4-O-allyl-2-O-benzyl-6-O-triisopropylsilyl-1-thio-β-D-glucopyranoside (356047-05-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / imidazole / dimethylformamide / 4 h / 20 °C

2: 90 percent / NaH / dimethylformamide / 3 h / 20 °C

3: 95 percent / DDQ; H₂O / CH₂Cl₂ / 5 h

With 1H-imidazole; water; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200106)2001:11<2055::AID-EJOC2055>3.0.CO;2-N

Reference yield:

ethyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside (174172-99-7) → ethyl 4-O-allyl-2-O-benzyl-6-O-triisopropylsilyl-1-thio-β-D-glucopyranoside (356047-05-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / NaH / dimethylformamide / 2 h / 20 °C

2: 77 percent / CSA / CH₂Cl₂; methanol / 20 h / 20 °C

3: 93 percent / imidazole / dimethylformamide / 4 h / 20 °C

4: 90 percent / NaH / dimethylformamide / 3 h / 20 °C

5: 95 percent / DDQ; H₂O / CH₂Cl₂ / 5 h

With 1H-imidazole; camphor-10-sulfonic acid; water; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200106)2001:11<2055::AID-EJOC2055>3.0.CO;2-N

upstream raw materials:

ethyl 4-O-allyl-2-O-benzyl-3-O-(4-methoxybenzyl)-6-O-triisopropylsilyl-1-thio-β-D-glucopyranoside

triisopropylsilyl chloride

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

ethyl 2-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside