2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-benzoylcephalomannine

Base Information

• Chemical Name: 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-benzoylcephalomannine
• CAS No.: 1329497-56-4
• Molecular Formula: C₅₁H₆₆N₄O₁₄Si
• Molecular Weight: 987.189
• Mol file: 1329497-56-4.mol

Synonyms:2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-benzoylcephalomannine

Chemical Property of 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-benzoylcephalomannine

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-benzoylcephalomannine

There total 6 articles about 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-benzoylcephalomannine 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: 92.9%

2-debenzoyl-2-m-N3-benzoylcephalomannine (959963-38-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoylcephalomannine (1329497-56-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 40 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.06.034

Reference yield:

2'-O-(t-butyldimethylsilyl)-7-O-(triethylsilyl)cephalomannine (1127890-27-0) → 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoylcephalomannine (1329497-56-4)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide / toluene / 13 h / 65 °C / Inert atmosphere

3: pyridine; hydrogen fluoride / water; acetonitrile / 20 °C

4: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere

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

DOI:10.1016/j.bmcl.2011.06.034

Reference yield:

2'-O-(t-butyldimethylsilyl)-2-debenzoyl-7-O-(triethylsilyl)cephalomannine (1127890-28-1) → 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoylcephalomannine (1329497-56-4)

Guidance literature:

Multi-step reaction with 3 steps

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

2: pyridine; hydrogen fluoride / water; acetonitrile / 20 °C

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

With pyridine; 1H-imidazole; hydrogen fluoride; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/j.bmcl.2011.06.034

upstream raw materials:

C₅₁H₆₇NO₁₄Si

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

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

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