cis-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopenten-1-ol

Base Information

• Chemical Name: cis-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopenten-1-ol
• CAS No.: 125974-13-2
• Molecular Formula: C₂₀H₃₄O₂Si
• Molecular Weight: 334.574
• Mol file: 125974-13-2.mol

Synonyms:cis-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopenten-1-ol

Chemical Property of cis-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopenten-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopenten-1-ol

There total 1 articles about cis-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopenten-1-ol 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:

6-oxabicyclo[3.1.0]hex-2-ene (7129-41-1) + (3S)-3-(tert-butyldimethyl-siloxy)-3-cyclohexylprop-1-yne (91098-88-3) → cis-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopenten-1-ol (125974-13-2)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1) hexane, 0 deg C, 15 min, 2) rt;

DOI:10.1021/jo00296a076

Reference yield: 88.0%

cis-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopenten-1-ol (125974-13-2) + benzoic acid (65-85-0,8013-63-6) → trans-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopentenyl Benzoate (125974-14-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jo00296a076

Reference yield:

cis-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopenten-1-ol (125974-13-2) → trans-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopenten-1-ol (125974-15-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature

2: 92 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

With lithium aluminium tetrahydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo00296a076

upstream raw materials:

6-oxabicyclo[3.1.0]hex-2-ene

(3S)-3-(tert-butyldimethyl-siloxy)-3-cyclohexylprop-1-yne

Downstream raw materials:

trans-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopentenyl Benzoate

trans-4-(3-((tert-Butyldimethylsilyl)oxy)-3-cyclohexyl-1-propynyl)-2-cyclopenten-1-ol