2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-10-Boc-7-methylaminocarbonyl-10-deacetylcephalomannine

Base Information

• Chemical Name: 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-10-Boc-7-methylaminocarbonyl-10-deacetylcephalomannine
• CAS No.: 1329497-66-6
• Molecular Formula: C₅₆H₇₅N₅O₁₆Si
• Molecular Weight: 1102.32

Synonyms:2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-10-Boc-7-methylaminocarbonyl-10-deacetylcephalomannine

Chemical Property of 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-10-Boc-7-methylaminocarbonyl-10-deacetylcephalomannine

Chemical Property:

Purity/Quality:

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Technology Process of 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-10-Boc-7-methylaminocarbonyl-10-deacetylcephalomannine

There total 11 articles about 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-10-Boc-7-methylaminocarbonyl-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-N3-10-Boc-7-imidazolylcarbonyl-10-deacetylcephalomannine (1329497-65-5) + methylamine (74-89-5) → 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-10-Boc-7-methylaminocarbonyl-10-deacetylcephalomannine (1329497-66-6)

Guidance literature:

In isopropyl alcohol; at 40 ℃; for 3.5h;

DOI:10.1016/j.bmcl.2011.06.034

Reference yield:

C51H67NO14Si (944454-50-6) → 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-10-Boc-7-methylaminocarbonyl-10-deacetylcephalomannine (1329497-66-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

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

3.1: 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide / toluene / 13 h / 65 °C / Inert atmosphere

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

5.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere

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

7.1: cerium(III) chloride / tetrahydrofuran / 0.17 h / Inert atmosphere

7.2: 18 h / 30 °C / Inert atmosphere

8.1: dmap / toluene / 2 h / 60 °C / Inert atmosphere

9.1: isopropyl alcohol / 3.5 h / 40 °C

With pyridine; 1H-imidazole; dmap; cerium(III) chloride; hydrogen fluoride; N-benzyl-trimethylammonium hydroxide; 4-pyrrolidin-1-ylpyridine; hydrazine hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1016/j.bmcl.2011.06.034

Reference yield:

2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoyl-10-deacetylcephalomannine (1329497-59-7) → 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-10-Boc-7-methylaminocarbonyl-10-deacetylcephalomannine (1329497-66-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: cerium(III) chloride / tetrahydrofuran / 0.17 h / Inert atmosphere

1.2: 18 h / 30 °C / Inert atmosphere

2.1: dmap / toluene / 2 h / 60 °C / Inert atmosphere

3.1: isopropyl alcohol / 3.5 h / 40 °C

With dmap; cerium(III) chloride; In tetrahydrofuran; isopropyl alcohol; toluene;

DOI:10.1016/j.bmcl.2011.06.034

upstream raw materials:

C₅₁H₆₇NO₁₄Si

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

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

2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N₃-10-Boc-7-imidazolylcarbonyl-10-deacetylcephalomannine

Downstream raw materials:

C₄₅H₅₃N₅O₁₄

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