(1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol

Base Information

• Chemical Name: (1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol
• CAS No.: 60410-16-4
• Molecular Formula: C7H10O3
• Molecular Weight: 142.155
• Hs Code.: 29162000
• European Community (EC) Number: 611-973-1,875-433-9
• DSSTox Substance ID: DTXSID00436209
• Nikkaji Number: J679.175A
• Wikidata: Q72434326
• Mol file: 60410-16-4.mol

Synonyms:60410-16-4;(1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol;(1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate;(1R,4S)-4-hydroxycyclopent-2-enyl acetate;(1S,4R)-4-Acetoxy-2-cyclopenten-1-ol;[(1R,4S)-4-hydroxycyclopent-2-en-1-yl] acetate;(1R,3S)-(+)-4-CYCLOPENTENE-1,3-DIOL 1-ACETATE;(1R,3S)-(+)-cis-4-Cyclopentene-1,3-diol 1-acetate;rel-(1R,4S)-4-Hydroxycyclopent-2-en-1-yl acetate;60410-18-6;(1R,4S)-4-hydroxy-2-cyclopenten-1-yl acetate;cis-(1R,4S)-4-Hydroxycyclopent-2-en-1-yl acetate;MFCD00078933;CIS-4-HYDROXYCYCLOPENT-2-ENYL ACETATE;(1R,3S)-4-Cyclopentene-1,3-diol 1-acetate;SCHEMBL254392;DTXSID00436209;IJDYOKVVRXZCFD-RQJHMYQMSA-N;5beta-Acetoxycyclopentene-3beta-ol;AMY34342;EX-A4107;(-)-cis-4-acetoxy-cyclopent-2-enol;AKOS025146560;(1S,4R)-4-acetoxycyclopent-2-en-1-ol;AS-37858;A8432;CS-0053603;(1S,4R)-cis 4-Acetoxy-2-cyclopenten-1-ol;4(s)-hydroxy-1 (r)-acetoxy-cyclopent-2-ene;4-Cyclopentene-1,3-diol,1-acetate,(1S,3R)-;EN300-7416334;(+)-(1R-cis)-4-Cyclopentene-1,3-diol monoacetate;(1R,3S)-(+)-1-Acetoxy-3-hydroxy-4-cyclopentene;(1R,3S)-4-CYCLOPENTENE-1,3-DIOL1-ACETATE;rac-(1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate;Acetic acid (1R,4S)-4-hydroxycyclopent-2-enyl ester;(1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol, >=99%

Chemical Property of (1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol

Chemical Property:

• Appearance/Colour: white to light yellow solid
• Vapor Pressure: 0.051mmHg at 25°C
• Melting Point: 49-52 °C
• Refractive Index: 1.5
• Boiling Point: 207.984 °C at 760 mmHg
• PKA: 14.11±0.40(Predicted)
• Flash Point: 83.718 °C
• PSA: 46.53000
• Density: 1.171 g/cm³
• LogP: 0.23890
• Storage Temp.: Store at +2°C to +8°C.
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 142.062994177
• Heavy Atom Count: 10
• Complexity: 162

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC(C=C1)O
• Isomeric SMILES: CC(=O)O[C@@H]1C[C@@H](C=C1)O
• Uses: (1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol can be used as:A building block for the synthesis of biologically significant carbocyclic nucleosides and prostaglandins.A starting material in the synthesis of azasugar analogs.

Technology Process of (1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol

There total 38 articles about (1S,4R)-cis-4-Acetoxy-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: 96.0%

cis-1,4-diacetoxy-2-cyclopentene (54664-61-8) → (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4)

Guidance literature:

With Novosyme sp 435 lipase; In various solvent(s); at 20 ℃; for 18h; pH=8;

DOI:10.1055/s-2007-967937

Reference yield: 95.0%

cis-1,4-diacetoxy-2-cyclopentene (54664-61-8) → (1S,4R)-4-hydroxy-2-cyclopentenyl acetate (60176-77-4) + (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4)

Guidance literature:

With methanol; lipase B from Candida antarctica; In tert-butyl methyl ether; at 5 ℃; for 16h; enantioselective reaction; Enzymatic reaction;

DOI:10.1016/j.tet.2018.09.052

Reference yield: 91.0%

(-)-acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester (61305-31-5) → (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; ethyl acetate;

upstream raw materials:

acetic anhydride

vinyl acetate

cis-4-cyclopentene-1,3-diol

2,2,2-trichloroethyl acetate

Downstream raw materials:

(+)-(2R,S)-methyl 2-<(1R,4S)-4-hydroxy-2-cyclopenten-1-yl>-2-(phenylsulfonyl)acetate

(1S,3S)-1-hydroxy-3-(methyl-carboxymethyl)-4-cyclopentene

(1R,4S)-(-)-4-triisopropylsilyloxy-2-cyclopenten-1-ol acetate

(1S)-cis-4-Benzyloxymethylcyclopent-2-en-1-ol

Refernces

• 1、 Reetz, Manfred T.,Becker, Michael H.,Klein, Heinz-Werner,Stoeckigt, Detlef. "A method for high-throughput screening of enantioselective catalysts". . p. 1758 - 1761. Retrieved 1999.
• 2、 Siddiqi,Oertel,Chen,Schneller. "Enantiospecific synthesis of the fluoro and epimeric derivatives of 5'-Noraristeromycin". . p. 708 - 709. Retrieved 1993.
• 3、 Deardorff, Donald R.,Matthews, A. J.,McMeekin, D. Scott,Craney, Chris L.. "A HIGHLY ENANTIOSELECTIVE HYDROLYSIS OF CIS-3,5-DIACETOXYCYCLOPENT-1-ENE. AN ENZYMATIC PREPARATION OF 3(R)-ACETOXY-5(S)-HYDROXYCYCLOPENT-1-ENE.". . p. 1255 - 1256. Retrieved 1986.
• 4、 Delayre, Bastien,Fung, Cédric,Wang, Qian,Zhu, Jieping. "Enantioselective Total Synthesis of (+)-Nordasycarpidone, (+)-Dasycarpidone, and (+)-Uleine". . . Retrieved 2021/07/12.
• 5、 Delayre, Bastien,Piemontesi, Cyril,Wang, Qian,Zhu, Jieping. "TiCl3-Mediated Synthesis of 2,3,3-Trisubstituted Indolenines: Total Synthesis of (+)-1,2-Dehydroaspidospermidine, (+)-Condyfoline, and (?)-Tubifoline". supporting information. p. 13990 - 13997. Retrieved 2020/06/10.