(1S,2R)-2-(Benzyloxymethyl)-1-hydroxy-3-cyclopentene

Base Information

• Chemical Name: (1S,2R)-2-(Benzyloxymethyl)-1-hydroxy-3-cyclopentene
• CAS No.: 110567-21-0
• Molecular Formula: C13H16O2
• Molecular Weight: 204.269
• Hs Code.: 2909499000
• DSSTox Substance ID: DTXSID70450876
• Nikkaji Number: J883.900J
• Wikidata: Q72502259
• Mol file: 110567-21-0.mol

Synonyms:110567-21-0;(1S,2R)-2-(BENZYLOXYMETHYL)-1-HYDROXY-3-CYCLOPENTENE;(1S,2R)-2-[(benzyloxy)methyl]cyclopent-3-en-1-ol;(1S,2R)-2-(phenylmethoxymethyl)cyclopent-3-en-1-ol;MFCD09263486;3-Cyclopenten-1-ol, 2-[(phenylmethoxy)methyl]-, (1S,2R)-;(1S, 2R)-2-(BENZYLOXYMETHYL)-1-HYDROXY-3-CYCLOPENTENE;(1S,2R)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol;(1S,2R)-2-(benzyloxymethyl)cyclopent-3-en-1-ol;SCHEMBL2512920;DTXSID70450876;WACMQXMZXZTKIV-OLZOCXBDSA-N;AMY30765;AKOS015917784;CS-W005682;GS-4072;A855329;J-500407;(1S,2R)-2-[(Benzyloxy)methyl]-3-cyclopenten-1-ol;(1S)-2beta-(Benzyloxymethyl)-3-cyclopentene-1alpha-ol

Chemical Property of (1S,2R)-2-(Benzyloxymethyl)-1-hydroxy-3-cyclopentene

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.565
• Boiling Point: 318.906 °C at 760 mmHg
• PKA: 14.65±0.40(Predicted)
• Flash Point: 135.492 °C
• PSA: 29.46000
• Density: 1.112 g/cm³
• LogP: 2.14020
• Solubility.: Chloroform, DCM, Ethyl Acetate
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 204.115029749
• Heavy Atom Count: 15
• Complexity: 207

Purity/Quality:

98%min ^*data from raw suppliers

(1S,2R)-2-((Benzyloxy)methyl)cyclopent-3-enol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CC(C1O)COCC2=CC=CC=C2
• Isomeric SMILES: C1C=C[C@@H]([C@H]1O)COCC2=CC=CC=C2
• Uses: (1S,2R)-2-((Benzyloxy)methyl)cyclopent-3-enol is an intermediate in the synthesis of Entecavir (E558900), an oral antiviral drug used in the treatment of hepatitis B infection.

Technology Process of (1S,2R)-2-(Benzyloxymethyl)-1-hydroxy-3-cyclopentene

There total 17 articles about (1S,2R)-2-(Benzyloxymethyl)-1-hydroxy-3-cyclopentene 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: 82.0%

(3R,4S)-3-benzyloxymethylhepta-1,6-dien-4-ol → (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene (110567-21-0)

Guidance literature:

With modified Grubb's catalyst; SBA-15; In cyclohexane; at 25 ℃; for 3h;

Reference yield: 73.0%

Benzyloxymethyl chloride (3587-60-8) + sodium cyclopentadienylide (4984-82-1) → (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene (110567-21-0)

Guidance literature:

Benzyloxymethyl chloride; sodium cyclopentadienylide; In tetrahydrofuran; N,N-dimethyl-formamide; at -40 ℃; for 0.25h;

With L-diisopinocampheylborane; In tetrahydrofuran; at -10 ℃; for 48h;

With sodium hydroxide; dihydrogen peroxide; at 20 ℃; for 12h; Further stages.;

DOI:10.1021/ja0258778

Reference yield: 25.0%

Benzyloxymethyl chloride (3587-60-8) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene (110567-21-0)

Guidance literature:

cyclopenta-1,3-diene; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

Benzyloxymethyl chloride; In tetrahydrofuran; at -60 ℃; for 2h; Further stages;

DOI:10.1080/15257770.2012.737970

upstream raw materials:

5-(benzyloxymethyl)cyclopentadiene

Benzyloxymethyl chloride

sodium cyclopentadienylide

(1R,4S,5S)-5-((benzyloxy)methyl)-4-((4-methoxybenzyl)oxy)cyclopent-2-enol

Downstream raw materials:

Toluene-4-sulfonic acid (1S,2R)-2-benzyloxymethyl-cyclopent-3-enyl ester

(R)-4-hydroxy-2-benzyloxymethylcyclopent-2-en-1-one

(1R,4S)-3-[(benzyloxy)methyl]-4-{[tert-butyl(dimethyl)silyl]-oxy}cyclopent-2-en-1-ol

((1S,2S,3S,5R)-2-Benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-3-yloxy)-tert-butyl-dimethyl-silane

Refernces

• 1、 -. "PCSK9 INHIBITORS AND METHODS OF USE THEREOF". Page/Page column 145-146. . Retrieved 2020/07/31.
• 2、 -. "Preparation method of optical pure cyclopentene alcohol serving as medical intermediate". Paragraph 0041; 0042. . Retrieved 2017/10/09.