(1S)-TRANS-1,2-CYCLOPENTANEDIOL

Base Information

• Chemical Name: (1S)-TRANS-1,2-CYCLOPENTANEDIOL
• CAS No.: 63261-45-0
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.133
• Mol file: 63261-45-0.mol

Synonyms:(S,S)-cyclopentane-1,2-diol

Chemical Property of (1S)-TRANS-1,2-CYCLOPENTANEDIOL

Chemical Property:

• Vapor Pressure: 0.0304mmHg at 25°C
• Melting Point: 46-50?°C
• Refractive Index: 1.4840 (estimate)
• Boiling Point: 136?°C/21.5?mmHg(lit.)
• Flash Point: 113?°C
• Density: 1.0042 (rough estimate)
• Storage Temp.: 2-8°C

Purity/Quality:

99.3% ^*data from raw suppliers

(1S)-TRANS-1,2-CYCLOPENTANEDIOL 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S)-TRANS-1,2-CYCLOPENTANEDIOL

There total 31 articles about (1S)-TRANS-1,2-CYCLOPENTANEDIOL 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%

(1S,2S)-(+)-1,2-bis(phenylmethoxy)cyclopentane (113350-83-7) → (S,S)-cyclopentane-1,2-diol (63261-45-0,86703-52-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 5h; under 4560 Torr;

DOI:10.1021/jo00243a048

Reference yield: 85.0%

Cyclopentene oxide (285-67-6) → (S,S)-cyclopentane-1,2-diol (63261-45-0,86703-52-8)

Guidance literature:

With water; In acetonitrile; at 23 ℃; for 24h; enantioselective reaction;

DOI:10.1016/j.tet.2014.03.043

Reference yield: 47.0%

trans-cyclopentane-1,2-diol (5057-99-8,86703-52-8) → (1R,2R)-cyclopentane-1,2-diol (930-46-1,86703-52-8) + (S,S)-cyclopentane-1,2-diol (63261-45-0,86703-52-8) + (2S)-2-hydroxycyclopentan-1-one (147333-12-8,473-84-7)

Guidance literature:

With oxygen; potassium carbonate; In water; at 60 ℃; for 168h; under 760.051 Torr; enantioselective reaction;

DOI:10.1021/jacs.6b12113

upstream raw materials:

trans-cyclopentane-1,2-diol

(2S)-2-hydroxycyclopentan-1-one

(+/-)-trans-1,2-diacetoxycyclopentane

(1S,2S)-(+)-1,2-bis(phenylmethoxy)cyclopentane

Downstream raw materials:

(1S,2R)-2-(phenylselanyl)cyclopentanol

(1R,2R)-1,2-bis(phenylselanyl)cyclopentane

(1S,2S)-(+)-trans-2-methoxycyclopentanol

(1S,2S)-2-(benzyloxy)cyclopentan-1-ol

Refernces

• 1、 Sun, Zhoutong,Wu, Lian,Bocola, Marco,Chan, H. C. Stephen,Lonsdale, Richard,Kong, Xu-Dong,Yuan, Shuguang,Zhou, Jiahai,Reetz, Manfred T.. "Structural and Computational Insight into the Catalytic Mechanism of Limonene Epoxide Hydrolase Mutants in Stereoselective Transformations". . p. 310 - 318. Retrieved 2018/01/17.
• 2、 Fujii, Kazuki,Mitsudo, Koichi,Mandai, Hiroki,Suga, Seiji. "Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts". supporting information. p. 2778 - 2788. Retrieved 2017/08/23.