(-)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-dihydroxyl-4-hydroxymethylcyclopentane

Base Information

• Chemical Name: (-)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-dihydroxyl-4-hydroxymethylcyclopentane
• CAS No.: 341553-94-4
• Molecular Formula: C₁₃H₁₈O₄
• Molecular Weight: 238.284
• Mol file: 341553-94-4.mol

Synonyms:(-)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-dihydroxyl-4-hydroxymethylcyclopentane

Chemical Property of (-)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-dihydroxyl-4-hydroxymethylcyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-dihydroxyl-4-hydroxymethylcyclopentane

There total 3 articles about (-)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-dihydroxyl-4-hydroxymethylcyclopentane 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: 97.0%

(3aR,4R,6S,6aS)-4-Benzyloxy-6-tert-butoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole (341553-93-3) → (-)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-dihydroxyl-4-hydroxymethylcyclopentane (341553-94-4)

Guidance literature:

With trifluoroacetic acid; In water; at 60 ℃;

DOI:10.1021/ol015783n

Reference yield:

benzyl bromide (100-39-0) → (-)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-dihydroxyl-4-hydroxymethylcyclopentane (341553-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / NaH / tetrahydrofuran / 0 °C

2: 97 percent / TFA / H₂O / 60 °C

With sodium hydride; trifluoroacetic acid; In tetrahydrofuran; water;

DOI:10.1021/ol015783n

Reference yield:

(1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol (192118-38-0) → (-)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-dihydroxyl-4-hydroxymethylcyclopentane (341553-94-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / NaH / tetrahydrofuran / 0 °C

2: 97 percent / TFA / H₂O / 60 °C

With sodium hydride; trifluoroacetic acid; In tetrahydrofuran; water;

DOI:10.1021/ol015783n

upstream raw materials:

(3aR,4R,6S,6aS)-4-Benzyloxy-6-tert-butoxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

benzyl bromide

(1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol

Downstream raw materials:

Benzoic acid (1R,2S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl ester

(2R,3aR,9aS)-2-Benzyloxy-5,5,7,7-tetraisopropyl-hexahydro-4,6,8-trioxa-5,7-disila-cyclopentacyclooctene

Benzoic acid (1R,2S,4R)-2-hydroxymethyl-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl ester

(+)-(2R,4R)-1-difluoro-2-O-benzyloxy-4-(O-trityloxymethyl)cyclopentane