2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-benzoyl-7-O-(triethylsilyl)cephalomannine

Base Information

• Chemical Name: 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-benzoyl-7-O-(triethylsilyl)cephalomannine
• CAS No.: 1127890-30-5
• Molecular Formula: C₅₇H₈₀N₄O₁₄Si₂
• Molecular Weight: 1101.45
• Mol file: 1127890-30-5.mol

Synonyms:2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-benzoyl-7-O-(triethylsilyl)cephalomannine

Chemical Property of 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-benzoyl-7-O-(triethylsilyl)cephalomannine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-benzoyl-7-O-(triethylsilyl)cephalomannine

There total 5 articles about 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-benzoyl-7-O-(triethylsilyl)cephalomannine 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: 82.9%

3-azidobenzoic acid (1843-35-2) + 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-7-O-(triethylsilyl)cephalomannine (1127890-28-1) → 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoyl-7-O-(triethylsilyl)cephalomannine (1127890-30-5)

Guidance literature:

With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In toluene; at 65 ℃; for 13h; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.06.034

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoyl-7-O-(triethylsilyl)cephalomannine (1127890-30-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere

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

3: N-benzyl-trimethylammonium hydroxide / methanol; dichloromethane / -65 - -10 °C / Inert atmosphere

4: 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide / toluene / 13 h / 65 °C / Inert atmosphere

With 1H-imidazole; N-benzyl-trimethylammonium hydroxide; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2011.06.034

Reference yield:

C51H67NO14Si (944454-50-6) → 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoyl-7-O-(triethylsilyl)cephalomannine (1127890-30-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

2: N-benzyl-trimethylammonium hydroxide / methanol; dichloromethane / -65 - -10 °C / Inert atmosphere

3: 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide / toluene / 13 h / 65 °C / Inert atmosphere

With 1H-imidazole; N-benzyl-trimethylammonium hydroxide; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2011.06.034

upstream raw materials:

C₅₁H₆₇NO₁₄Si

2'-O-(t-butyldimethylsilyl)-7-O-(triethylsilyl)cephalomannine

3-azidobenzoic acid

2'-O-(t-butyldimethylsilyl)-2-debenzoyl-7-O-(triethylsilyl)cephalomannine

Downstream raw materials:

2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-benzoyl-10-deacetylcephalomannine

2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-10-O-trimethylsilyl-10-deacetylcephalomannine

C₅₆H₇₆N₄O₁₄Si₂

C₅₉H₈₃N₅O₁₆Si₂