(1S,5S)-5-(hydroxymethyl)cyclopent-2-enol

Base Information

• Chemical Name: (1S,5S)-5-(hydroxymethyl)cyclopent-2-enol
• CAS No.: 151765-20-7
• Molecular Formula: C6H10O2
• Molecular Weight: 114.144
• DSSTox Substance ID: DTXSID90447086
• Wikidata: Q82265871
• Mol file: 151765-20-7.mol

Synonyms:(1S,5S)-5-(hydroxymethyl)cyclopent-2-enol;151765-20-7;(1S,5S)-5-(hydroxymethyl)cyclopent-2-en-1-ol;76909-91-6;(1S,2S)-2-Hydroxy-3-cyclopentene-1-methanol;cis-5-(Hydroxymethyl)cyclopent-2-enol;SCHEMBL191431;DTXSID90447086;WBEXVFLBMXJLAO-WDSKDSINSA-N;CS-M0199;D77369

Chemical Property of (1S,5S)-5-(hydroxymethyl)cyclopent-2-enol

Chemical Property:

• PSA: 40.46000
• LogP: -0.08430
• Solubility.: Ethyl Acetate, Methanol
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 114.068079557
• Heavy Atom Count: 8
• Complexity: 98.7

Purity/Quality:

97% ^*data from raw suppliers

(1S,2S)-2-Hydroxy-3-cyclopentene-1-methanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CC(C1CO)O
• Isomeric SMILES: C1C=C[C@@H]([C@@H]1CO)O
• Uses: (1S,2S)-2-Hydroxy-3-cyclopentene-1-Methanol can be used in the enantioselective synthesis of a variety of inhibitors and antiviral agents.

Technology Process of (1S,5S)-5-(hydroxymethyl)cyclopent-2-enol

There total 5 articles about (1S,5S)-5-(hydroxymethyl)cyclopent-2-enol 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: 66.3%

[3(1R,2S),4R]-4-benzyl-3-(2-hydroxycylopent-3-enecarbonyl)oxazolidin-2-one (1005006-70-1) → (1S,5S)-5-hydroxymethyl-2-cyclopenten-1-ol (151765-20-7)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 1.75h;

DOI:10.1016/j.tet.2007.10.054

Reference yield: 60.0%

(1S,5R)-5-(Hydroxy-methoxy-methyl)-cyclopent-2-enol → (1S,5S)-5-hydroxymethyl-2-cyclopenten-1-ol (151765-20-7)

Guidance literature:

With sodium tetrahydroborate; at 0 ℃; for 0.5h;

DOI:10.1016/0040-4039(95)01060-U

Reference yield:

(1R,2S)-2-Hydroxy-cyclopent-3-enecarbaldehyde → (1S,5S)-5-hydroxymethyl-2-cyclopenten-1-ol (151765-20-7)

Guidance literature:

With sodium tetrahydroborate; In ethanol;

DOI:10.1039/a708261d

upstream raw materials:

[3(1R,2S),4R]-4-benzyl-3-(2-hydroxycylopent-3-enecarbonyl)oxazolidin-2-one

Downstream raw materials:

(1S,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopent-2-en-1-ol

(1S,5S)-5-({[tert-Butyl(diphenyl)silyl]oxy}methyl)cyclopent-2-en-1-ol

O-[(4aS,6S,7S,7aR)-6-({[(1S)-2,3-dihydro-1H-inden-1-ylamino]-pyrimidin-4-yl}-methyl)-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-yl]-O-phenyl thiocarbonate

(4aS,6S,7S,7aR)-6-({6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-pyrimidin-4-yl}-methyl)-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-7-ol

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