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

Base Information

• Chemical Name: (1R,4S)-cis-4-Acetoxy-2-cyclopenten-1-ol
• CAS No.: 60176-77-4
• Molecular Formula: C7H10O3
• Molecular Weight: 142.155
• Hs Code.: 2915390090
• European Community (EC) Number: 875-433-9
• DSSTox Substance ID: DTXSID10431801
• Nikkaji Number: J774.684I
• Wikidata: Q76414614
• Mol file: 60176-77-4.mol

Synonyms:60176-77-4;(1R,4S)-cis-4-Acetoxy-2-cyclopenten-1-ol;[(1S,4R)-4-hydroxycyclopent-2-en-1-yl] acetate;cis-4-Hydroxycyclopent-2-en-1-yl acetate;(1S,4R)-cis-4-Hydroxy-2-cyclopentenyl acetate;(1R,4S)-4-acetoxy-2-cyclopenten-1-ol;4-Cyclopentene-1,3-diol, monoacetate, cis-;CIS-4-HYDROXYCYCLOPENT-2-ENYL ACETATE;60410-18-6;(1R,3S)-(+)-cis-4-Cyclopentene-1,3-diol 1-acetate;SCHEMBL307800;DTXSID10431801;IJDYOKVVRXZCFD-NKWVEPMBSA-N;MFCD00210003;AKOS006238828;4beta-Acetoxy-2-cyclopentene-1beta-ol;cis-3-acetoxy-5-hydroxycyclopent-1-ene;cis-4-Hydroxycyclopent-2-en-1-ylacetate;AS-37859;(1R,4S)-4-hydroxycyclopent-2-enylacetate;(1S,4R)-4-hydroxy-2-cyclopentenol acetate;(1S,4R)-4-hydroxy-2-cyclopentenyl acetate;(1S,4R)-4-hydroxycyclopent-2-enyl acetate;[cis-4-Hydroxycyclopent-2-en-1-yl] acetate;CS-0183432;A858137;J-500360;(1S,4R)-4-HYDROXYCYCLOPENT-2-EN-1-YL ACETATE;acetic acid (1S,4R)-4-hydroxy-cyclopent-2-enyl ester;(1R,4S)-cis-4-Acetoxy-2-cyclopenten-1-ol, >=98.0% (sum of enantiomers, GC)

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

Chemical Property:

• Melting Point: 49-51 °C
• Boiling Point: 207.984 °C at 760 mmHg
• 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:

99%, ^*data from raw suppliers

(1R,3S)-(+)-cis-4-Cyclopentene-1,3-diol 1-acetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

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: (1R,4S)-cis-4-Acetoxy-2-cyclopenten-1-ol can be used as a reactant in the total synthesis of Bartlett′s brefeldin intermediate, spinosyn A analogs, (+)-7-deaza-5′-noraristeromycin, (±) strychnine and the Wieland-Gumlich aldehyde.

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

There total 39 articles about (1R,4S)-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: 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: 87.0%

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

Guidance literature:

With sodium hydroxide; phosphate buffer; immobilized porcine liver esterase (PLE, E_. C_. 3.1.1.1) on Eupergit C; at 32 ℃; for 14h; pH= 7;

DOI:10.1016/S0040-4039(00)61896-8

Reference yield: 78.0%

vinyl acetate (108-05-4,9003-20-7) + cis-4-cyclopentene-1,3-diol (29783-26-4) → cis-1,4-diacetoxy-2-cyclopentene (54664-61-8) + (1S,4R)-4-hydroxy-2-cyclopentenyl acetate (60176-77-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 4h; Ambient temperature; lipase from Mucor sp.;

upstream raw materials:

vinyl acetate

cis-4-cyclopentene-1,3-diol

Isopropenyl acetate

2,2,2-trichloroethyl acetate

Downstream raw materials:

(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,4S)-4-acetoxy-cyclopent-2-enyl ester

(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

(1S,4R)-N-[9-(4-hydroxy-2-cyclopenten-1-yl)-9H-purin-6-yl]benzamide

Refernces

• 1、 Shizuka, Manami,Snapper, Marc L.. "Selective synthesis of ent-15-epi-F2t-isoprostane and a deuterated derivative". . p. 2397 - 2403. Retrieved 2007.
• 2、 Kalkote, Uttam R.,Ghorpade, Sandeep R.,Joshi, Rohini R.,Ravindranathan,Bastawade, Kulbhushan B.,Gokhale, Digambar V.. "A practical and scalable process for 4-(R)-hydroxycyclopent-2-en-1-(S)- acetate by desymmetrization of meso-cyclopent-2-en-1,4-diacetate catalyzed by Trichosporon beigelii (NCIM 3326), a cheap biocatalyst". . p. 2965 - 2970. Retrieved 2000.
• 3、 Kimbrough, Jennifer R.,Jana, Somnath,Kim, Kwangho,Allweil, Alexander,Oates, John A.,Milne, Ginger L.,Sulikowski, Gary A.. "Synthesis of tetranor-PGE1: A urinary metabolite of prostaglandins E1 and E2". supporting information. . Retrieved 2020/04/21.
• 4、 Putta, Shekhar,Reddy, Annem Mallikarjun,Sheelu, Gurrala,Reddy, B.V. Subba,Kumaraguru, Thenkrishnan. "Preparation of (1R,4S)-4-hydroxycyclopent-2-en-1-yl acetate via Novozym-435 catalyzed desymmetrization of cis-3,5-Diacetoxy-1-cyclopentene". . p. 6673 - 6679. Retrieved 2018/10/15.