Butyl-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester

Base Information

• Chemical Name: Butyl-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester
• CAS No.: 190264-75-6
• Molecular Formula: C₁₄H₂₁NO₃
• Molecular Weight: 251.326
• Mol file: 190264-75-6.mol

Synonyms:Butyl-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester

Chemical Property of Butyl-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Butyl-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester

There total 2 articles about Butyl-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester 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: 78.0%

N-butylamine (109-73-9,85404-21-3) + (3S,5R)-1-ethynyl-3-hydroxy-2-methyl-5-[(vinyloxy)carbonyloxy]-1-cyclohexene (190264-64-3) → Butyl-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester (190264-75-6)

Guidance literature:

In tetrahydrofuran; at 60 ℃; for 24h;

DOI:10.1021/jo970133b

Reference yield:

(3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene (113375-51-2) → Butyl-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester (190264-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / toluene / 4 h / 30 °C / Candida antarctica lipase SP 435L presence, other biologically active materials: Chromobacterium viscosum lipase, Pseudomonas cepacia lipase

2: 78 percent / tetrahydrofuran / 24 h / 60 °C

In tetrahydrofuran; toluene;

DOI:10.1021/jo970133b

Reference yield: 97.0%

tert-butyldimethylsilyl chloride (18162-48-6) + Butyl-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester (190264-75-6) → (3S,5R)-5-[N-(butylcarbamoyl)oxy]-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene (796039-25-3)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2004.07.042

upstream raw materials:

N-butylamine

(3S,5R)-1-ethynyl-3-hydroxy-2-methyl-5-[(vinyloxy)carbonyloxy]-1-cyclohexene

(3S,5R)-1-ethynyl-3,5-dihydroxy-2-methylcyclohex-1-ene

Downstream raw materials:

(3S,5R)-5-[N-(butylcarbamoyl)oxy]-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

3-O-(N-butylcarbamoyl)-6,7-dehydro-1α,25-dihydroxyvitamin D3