(1s-trans)-2-[(phenylmethoxy)methyl]-3-cyclopenten-1-ol

Base Information

• Chemical Name: (1s-trans)-2-[(phenylmethoxy)methyl]-3-cyclopenten-1-ol
• CAS No.: 188399-48-6
• Molecular Formula: C13H16O2
• Molecular Weight: 204.269
• Mol file: 188399-48-6.mol

Synonyms:3-Cyclopenten-1-ol,2-[(phenylmethoxy)methyl]-, (1R-trans)- (9CI);(1R,2S)-2-[(Phenylmethoxy)methyl]-3-cyclopenten-1-ol;

Chemical Property of (1s-trans)-2-[(phenylmethoxy)methyl]-3-cyclopenten-1-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.565
• Boiling Point: 318.9 °C at 760 mmHg
• PKA: 14.65±0.40(Predicted)
• Flash Point: 135.5 °C
• PSA: 29.46000
• Density: 1.112 g/cm³
• LogP: 2.14020
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (1s-trans)-2-[(phenylmethoxy)methyl]-3-cyclopenten-1-ol is a reactant used in the preparation of carbocyclic deoxyguanosine analog with potent and selective anti-hepatitis B virus.

Technology Process of (1s-trans)-2-[(phenylmethoxy)methyl]-3-cyclopenten-1-ol

There total 5 articles about (1s-trans)-2-[(phenylmethoxy)methyl]-3-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: 40.0%

Benzyloxymethyl chloride (3587-60-8) + sodium cyclopentadienide → (1R,2S)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol (188399-48-6)

Guidance literature:

Benzyloxymethyl chloride; sodium cyclopentadienide; In N,N-dimethyl-formamide; at -40 - 20 ℃; for 0.5h;

With (-)-α-pinene; dimethylsulfide borane complex; In tetrahydrofuran; at -78 - 4 ℃; for 24.5h;

With dihydrogen peroxide; sodium hydroxide; In water; for 4h;

Reference yield:

5-(benzyloxymethyl)cyclopentadiene (39939-07-6) → (1R,2S)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol (188399-48-6) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

5-(benzyloxymethyl)cyclopentadiene; With diisopinocampheylborane; In tetrahydrofuran; at -20 - -18 ℃;

With dihydrogen peroxide; sodium hydroxide;

DOI:10.1021/op010209c

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (1R,2S)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol (188399-48-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / -78 - -65 °C

2: 1.) diisopinylcampheylborane (prepared from (-)-α-pinene, 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C

With sodium hydroxide; (-)-diisopinocampheylborane; dihydrogen peroxide; In tetrahydrofuran;

DOI:10.1016/S0960-894X(96)00594-X

upstream raw materials:

5-(benzyloxymethyl)cyclopentadiene

Benzyloxymethyl chloride

sodium cyclopentadienylide

Downstream raw materials:

C₂₀H₂₂O₂

(1R,2S)-2-(benzyloxymethyl)cyclopent-3-enyl sulfamate