(-)-(2S,3S)-2,3-Epoxy-3-cyclohexyl-1-propanol

Base Information

• Chemical Name: (-)-(2S,3S)-2,3-Epoxy-3-cyclohexyl-1-propanol
• CAS No.: 115362-12-4
• Molecular Formula: C9H16O2
• Molecular Weight: 156.225
• Mol file: 115362-12-4.mol

Synonyms:Oxiranemethanol,3-cyclohexyl-, (2S-trans)- (9CI);(-)-(2S,3S)-2,3-Epoxy-3-cyclohexyl-1-propanol;

Chemical Property of (-)-(2S,3S)-2,3-Epoxy-3-cyclohexyl-1-propanol

Chemical Property:

• Vapor Pressure: 0.00257mmHg at 25°C
• Refractive Index: 1.51
• Boiling Point: 254.8 °C at 760 mmHg
• Flash Point: 107.4 °C
• PSA: 32.76000
• Density: 1.092 g/cm³
• LogP: 1.32640

Purity/Quality:

98% ^*data from raw suppliers

(-)-(2S,3S)-2,3-EPOXY-3-CYCLOHEXYL-1-PROPANOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-(2S,3S)-2,3-Epoxy-3-cyclohexyl-1-propanol

There total 10 articles about (-)-(2S,3S)-2,3-Epoxy-3-cyclohexyl-1-propanol 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: 90.0%

cis S-tert-Butyl 3-cyclohexyloxirane-2-carbothioate (142528-81-2,142528-82-3) → cis 2-Hydroxymethyl-3-cyclohexyloxirane (85531-72-2,86990-94-5,99883-81-5,111902-61-5,115362-12-4,127851-94-9,142562-98-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 8h; Ambient temperature; or LiAlH₄/ether, -78 deg C, 1 h;

Reference yield: 55.0%

C15H25NO2S (1438398-81-2) → (-)-(2S,3S)-2,3-epoxy-3-cyclohexyl-1-propanol (115362-12-4)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; for 0.5h; Inert atmosphere;

DOI:10.1002/chem.201201332

Reference yield: 24.0%

C18H31NO3S → (2S,3R)-3-cyclohexyloxiranemethanol + (-)-(2S,3S)-2,3-epoxy-3-cyclohexyl-1-propanol (115362-12-4)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 0 - 25 ℃; Inert atmosphere;

DOI:10.1021/jo1025964

upstream raw materials:

(E)-3-cyclohexyl-2-propen-1-ol

(E)-3-cyclohexyl-acrylic acid ethyl ester

cyclohexanecarbaldehyde

3-cyclohexylacrylic acid methyl ester

Downstream raw materials:

(1S,2R)-1-cyclohexyl-2-methyl-1,3-propane diol

(1S,2R)-1-Cyclohexyl-2-vinyl-propane-1,3-diol

(R)-3-Cyclohexyl-propane-1,2-diol

(R)-1-Cyclohexyl-propane-1,3-diol

Refernces

• 1、 Sarabia, Francisco,Vivar-García, Carlos,García-Castro, Miguel,García-Ruiz, Cristina,Martín-Gálvez, Francisca,Sánchez-Ruiz, Antonio,Chammaa, Samy. "A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: Applications in asymmetric synthesis". supporting information. p. 15190 - 15201. Retrieved 2013/01/15.
• 2、 Nishizawa, Rena,Nishiyama, Toshihiko,Hisaichi, Katsuya,Minamoto, Chiaki,Matsunaga, Naoki,Takaoka, Yoshikazu,Nakai, Hisao,Jenkinson, Stephen,Kazmierski, Wieslaw M.,Tada, Hideaki,Sagawa, Kenji,Shibayama, Shiro,Fukushima, Daikichi,Maeda, Kenji,Mitsuya, Hiroaki. "Spirodiketopiperazine-based CCR5 antagonist: Discovery of an antiretroviral drug candidate". . p. 1141 - 1145. Retrieved 2011/04/16.