(1R,2R)-2-((Benzyloxy)Methyl)cyclopent-3-enol

Base Information

• Chemical Name: (1R,2R)-2-((Benzyloxy)Methyl)cyclopent-3-enol
• CAS No.: 325480-40-8
• Molecular Formula: C₁₃H₁₆O₂
• Molecular Weight: 204.269
• Mol file: 325480-40-8.mol

Synonyms:(1R,2R)-2-benzyloxymethyl-3-cyclopenten-1-ol

Chemical Property of (1R,2R)-2-((Benzyloxy)Methyl)cyclopent-3-enol

Chemical Property:

• Boiling Point: 318.9±22.0 °C(Predicted)
• PKA: 14.65±0.40(Predicted)
• Density: 1.112±0.06 g/cm3(Predicted)

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (1R,2R)-2-((Benzyloxy)methyl)cyclopent-3-enol is an reactant used in the preparation of carbocyclic deoxyguanosine analog with potent and selective anti-hepatitis B virus.

Technology Process of (1R,2R)-2-((Benzyloxy)Methyl)cyclopent-3-enol

There total 6 articles about (1R,2R)-2-((Benzyloxy)Methyl)cyclopent-3-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: 89.0%

(1R,2R)-2-(benzyloxymethyl)cyclopent-3-en-1-yl 4-nitrobenzoate → (1R,2R)-2-benzyloxymethyl-3-cyclopenten-1-ol (325480-40-8)

Guidance literature:

(1R,2R)-2-(benzyloxymethyl)cyclopent-3-en-1-yl 4-nitrobenzoate; With potassium carbonate; In methanol; at 20 ℃; for 24h; Inert atmosphere;

With hydrogenchloride; In methanol; water; at 0 ℃; pH=1 - 2; Inert atmosphere;

DOI:10.1002/chem.201202374

Reference yield:

(1R,2R)-2-benzyloxymethyl-3-cyclopenten-1-yl benzoate (325480-41-9) → (1R,2R)-2-benzyloxymethyl-3-cyclopenten-1-ol (325480-40-8)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃;

DOI:10.1055/s-2006-926411

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (1R,2R)-2-benzyloxymethyl-3-cyclopenten-1-ol (325480-40-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH

2.1: diisopropylcamphenylborane

2.2: H₂O₂

3.1: 85 percent / Ph₃P; diethylazodicarboxylate / 0 - 20 °C

4.1: 3.32 mg / NaOH / methanol / 20 °C

With sodium hydroxide; diisopropylcamphenylborane; sodium hydride; triphenylphosphine; diethylazodicarboxylate; In methanol; 3.1: Mitsunobu reaction;

DOI:10.1021/jo001427r

upstream raw materials:

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

(1R,2R)-2-benzyloxymethyl-3-cyclopenten-1-yl benzoate

Benzyloxymethyl chloride

5-(benzyloxymethyl)cyclopentadiene

Downstream raw materials:

(3R,4S)-1-(benzyloxy)-3-((benzyloxy)methyl)-4-(hydroxy)piperidine

(3R,4S)-1-(allyloxy)-3-((benzyloxy)methyl)-4-(hydroxy)piperidine

(1R,2R)-1-(2-naphthylmethyl)oxy-2-benzyloxymethylcyclopent-3-ene

(1R,2R,3R,4R)-3-benzyloxymethyl-cyclopentane-1,2,4-triol

Refernces

• 1、 Ludek, Olaf R.,Kraemer, Tobias,Balzarini, Jan,Meier, Chris. "Divergent synthesis and biological evaluation of carbocyclic α-, iso- and 3′-epi-nucleosides and their lipophilic nucleotide prodrugs". . p. 1313 - 1324. Retrieved 2007/10/03.