3,4-di-O-benzoyl-2-deoxy-1-O-(2-hydroxyethyl)-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside

Base Information

• Chemical Name: 3,4-di-O-benzoyl-2-deoxy-1-O-(2-hydroxyethyl)-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside
• CAS No.: 1447811-17-7
• Molecular Formula: C₃₃H₄₄F₃NO₉Si
• Molecular Weight: 683.794
• Mol file: 1447811-17-7.mol

Synonyms:3,4-di-O-benzoyl-2-deoxy-1-O-(2-hydroxyethyl)-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside

Chemical Property of 3,4-di-O-benzoyl-2-deoxy-1-O-(2-hydroxyethyl)-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-benzoyl-2-deoxy-1-O-(2-hydroxyethyl)-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside

There total 6 articles about 3,4-di-O-benzoyl-2-deoxy-1-O-(2-hydroxyethyl)-2-trifluoroacetylamino-6-O-triisopropylsilyl-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: 89.0%

1-O-(2-benzyloxyethyl)-2-deoxy-3,4-di-O-benzoyl-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside (1447811-16-6) → 3,4-di-O-benzoyl-2-deoxy-1-O-(2-hydroxyethyl)-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside (1447811-17-7)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; hydrogen; In tetrahydrofuran; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.1016/j.bmcl.2013.05.036

Reference yield:

phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside (371123-22-7) → 3,4-di-O-benzoyl-2-deoxy-1-O-(2-hydroxyethyl)-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside (1447811-17-7)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 22 h / 20 °C / Inert atmosphere

2: pyridine / 0 - 20 °C / Inert atmosphere

3: pyridine / 20 h / 20 °C / Inert atmosphere

4: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 20 °C / Molecular sieve; Inert atmosphere

5: 20% palladium hydroxide-activated charcoal; hydrogen / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 20% palladium hydroxide-activated charcoal; hydrogen; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2013.05.036

Reference yield:

triisopropylsilyl chloride (13154-24-0) → 3,4-di-O-benzoyl-2-deoxy-1-O-(2-hydroxyethyl)-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside (1447811-17-7)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 22 h / 20 °C / Inert atmosphere

2: pyridine / 0 - 20 °C / Inert atmosphere

3: pyridine / 20 h / 20 °C / Inert atmosphere

4: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 20 °C / Molecular sieve; Inert atmosphere

5: 20% palladium hydroxide-activated charcoal; hydrogen / tetrahydrofuran / 72 h / 20 °C / Inert atmosphere

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 20% palladium hydroxide-activated charcoal; hydrogen; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2013.05.036

upstream raw materials:

phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside

triisopropylsilyl chloride

phenyl 2-amino-2-deoxy-1-thio-6-O-(triisopropylsilyl)-β-D-glucopyranoside

phenyl 2-deoxy-1-thio-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside

Downstream raw materials:

3,4-di-O-benzoyl-2-deoxy-1-O-[2-(4,4'-dimethoxytrityloxy)ethyl]-2-trifluoroacetylamino-β-D-glucopyranoside

C₄₉H₄₆F₃NO₁₄

3,4-di-O-benzoyl-2-deoxy-1-O-[2-(4,4'-dimethoxytrityloxy)ethyl]-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside