ethyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-1-thio-β-glucopyranoside

Base Information

• Chemical Name: ethyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-1-thio-β-glucopyranoside
• CAS No.: 215439-81-9
• Molecular Formula: C₃₂H₃₇NO₆SSi
• Molecular Weight: 591.8
• Mol file: 215439-81-9.mol

Synonyms:ethyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-1-thio-β-glucopyranoside

Chemical Property of ethyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-1-thio-β-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-1-thio-β-glucopyranoside

There total 5 articles about ethyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-1-thio-β-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:

C16H19NO6S + tert-butylchlorodiphenylsilane (58479-61-1) → ethyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-1-thio-β-glucopyranoside (215439-81-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1002/asia.201801486

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide (70831-94-6) → ethyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-1-thio-β-glucopyranoside (215439-81-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: thiourea / acetonitrile / 0.75 h / 80 °C

1.2: 0.5 h / 20 °C

2.1: sodium hydroxide; methanol / dichloromethane / 2 h / pH < 10

3.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

With 1H-imidazole; methanol; thiourea; sodium hydroxide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/asia.201801486

Reference yield:

C22H25NO9S → ethyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-1-thio-β-glucopyranoside (215439-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; methanol / dichloromethane / 2 h / pH < 10

2: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

With 1H-imidazole; methanol; sodium hydroxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/asia.201801486

upstream raw materials:

ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

tert-butylchlorodiphenylsilane

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

Downstream raw materials:

ethyl 6-O-(tert-butyldiohenylsilyl)-2-deoxy-3,4-di-O-(p-methylbenzoyl)-2-phthalimido-1-thio-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-{3-[2-deoxy-3,4-di-O-(p-methylbenzoyl)-2-phthalimido-β-D-glucopyranosyloxy]propyl}-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-{3-[6-O-(tert-butyldiphenylsilyl)-2-deoxy-3,4-di-O-(p-methylbenzoyl)-2-phthalimido-β-D-glucopyranosyloxy]propyl}-β-D-glucopyranoside