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

Base Information

• Chemical Name: (3S,5R)-5-[N-(butylcarbamoyl)oxy]-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene
• CAS No.: 796039-25-3
• Molecular Formula: C₂₀H₃₅NO₃Si
• Molecular Weight: 365.588
• Mol file: 796039-25-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

Reference yield:

25-trimethylsilyloxy-de-A,B-cholest-8-en-8-yl trifluoromethanesulfonate (222317-53-5) + (3S,5R)-5-[N-(butylcarbamoyl)oxy]-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene (796039-25-3) → Butyl-carbamic acid (1R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-3-[(1R,3aR,7aR)-1-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-ylethynyl]-4-methyl-cyclohex-3-enyl ester

Guidance literature:

With copper(l) iodide; diethylamine; bis(triphenylphosphine) palladium (Il) acetate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2004.07.042

Reference yield:

(3S,5R)-5-[N-(butylcarbamoyl)oxy]-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene (796039-25-3) → Butyl-carbamic acid (1R,5S)-5-hydroxy-3-{(Z)-2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]-vinyl}-4-methyl-cyclohex-3-enyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: CuI; Et₂NH / Pd(PPh₃)2(OAc)2 / dimethylformamide / 1 h / 20 °C

2: TBAF / tetrahydrofuran / 12 h / 20 °C

3: H₂; quinoline / Lindlar catalyst / methanol; hexane / 1 h / 20 °C

With quinoline; copper(l) iodide; tetrabutyl ammonium fluoride; hydrogen; diethylamine; Lindlar's catalyst; bis(triphenylphosphine) palladium (Il) acetate; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2004.07.042

upstream raw materials:

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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