2-(trimethylsilyl)ethyl 4-O-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-arabino-hexopyranosyl]-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 4-O-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-arabino-hexopyranosyl]-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 175844-69-6
• Molecular Formula: C₆₆H₆₇NO₁₅Si
• Molecular Weight: 1142.34
• Mol file: 175844-69-6.mol

Synonyms:2-(trimethylsilyl)ethyl 4-O-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-arabino-hexopyranosyl]-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 4-O-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-arabino-hexopyranosyl]-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 4-O-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-arabino-hexopyranosyl]-2,3,6-tri-O-benzyl-β-D-glucopyranoside

There total 1 articles about 2-(trimethylsilyl)ethyl 4-O-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-arabino-hexopyranosyl]-2,3,6-tri-O-benzyl-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: 86.0%

2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (117253-05-1) + 3,4,6-tri-O-benzoyl-2-(benzoyloximino)-2-deoxy-α-D-arabino-hexopyranosyl bromide (82469-72-5) → 2-(trimethylsilyl)ethyl 4-O-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-arabino-hexopyranosyl]-2,3,6-tri-O-benzyl-β-D-glucopyranoside (175844-69-6)

Guidance literature:

With 4 A molecular sieve; silver aluminosilicate; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1248/cpb.44.437

Reference yield:

2-(trimethylsilyl)ethyl 4-O-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-arabino-hexopyranosyl]-2,3,6-tri-O-benzyl-β-D-glucopyranoside (175844-69-6) → 4-O-(2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-β-D-glucopyranoside fluoride (142330-02-7)

Guidance literature:

Multi-step reaction with 4 steps

1: BH₃*THF / tetrahydrofuran / 1.) -10 deg C, 0.5 h, 2.) RT, 2 h

2: tetrahydrofuran / 1 h / Ambient temperature

3: 77 percent / CF₃COOH / CH₂Cl₂ / 2 h / 0 °C

4: diethylaminosulfur trifluoride / CH₂Cl₂ / 3 h / Ambient temperature

With borane-THF; diethylamino-sulfur trifluoride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.44.437

Reference yield:

2-(trimethylsilyl)ethyl 4-O-[3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-arabino-hexopyranosyl]-2,3,6-tri-O-benzyl-β-D-glucopyranoside (175844-69-6) → 4-O-(2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-D-glucopyranoside

Guidance literature:

Multi-step reaction with 3 steps

1: BH₃*THF / tetrahydrofuran / 1.) -10 deg C, 0.5 h, 2.) RT, 2 h

2: tetrahydrofuran / 1 h / Ambient temperature

3: 77 percent / CF₃COOH / CH₂Cl₂ / 2 h / 0 °C

With borane-THF; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.44.437

upstream raw materials:

2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

3,4,6-tri-O-benzoyl-2-(benzoyloximino)-2-deoxy-α-D-arabino-hexopyranosyl bromide

Downstream raw materials:

4-O-(2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-β-D-glucopyranoside fluoride

2-(trimethylsilyl)ethyl 4-O-(2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-β-D-glucopyranoside