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

Base Information

• Chemical Name: 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-10-O-trimethylsilyl-10-deacetylcephalomannine
• CAS No.: 1346571-55-8
• Molecular Formula: C₅₂H₇₂N₄O₁₃Si₂
• Molecular Weight: 1017.33

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

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

Chemical Property:

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

There total 9 articles about 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-10-O-trimethylsilyl-10-deacetylcephalomannine 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:

2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoyl-10-deacetylcephalomannine (1329497-59-7) + N,O-Bis(trimethylsilyl)trifluoroacetamide (25561-30-2) → 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-10-O-trimethylsilyl-10-deacetylcephalomannine (1346571-55-8)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.06.034

Reference yield:

C51H67NO14Si (944454-50-6) → 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-10-O-trimethylsilyl-10-deacetylcephalomannine (1346571-55-8)

Guidance literature:

Multi-step reaction with 7 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

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

5: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere

6: hydrazine hydrate / ethanol; water / 10 h / -20 - 0 °C

7: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -20 °C / Inert atmosphere

With pyridine; 1H-imidazole; hydrogen fluoride; N-benzyl-trimethylammonium hydroxide; 4-pyrrolidin-1-ylpyridine; hydrazine hydrate; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; 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-N3-10-O-trimethylsilyl-10-deacetylcephalomannine (1346571-55-8)

Guidance literature:

Multi-step reaction with 5 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

4: hydrazine hydrate / ethanol; water / 10 h / -20 - 0 °C

5: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -20 °C / Inert atmosphere

With pyridine; 1H-imidazole; hydrogen fluoride; 4-pyrrolidin-1-ylpyridine; hydrazine hydrate; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/j.bmcl.2011.06.034

upstream raw materials:

C₅₁H₆₇NO₁₄Si

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

N,O-Bis(trimethylsilyl)trifluoroacetamide

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

Downstream raw materials:

C₅₉H₈₃N₅O₁₆Si₂

C₄₇H₅₄N₄O₁₄

C₅₀H₆₁N₅O₁₆

C₄₆H₅₄N₄O₁₅

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