2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane

Base Information

• Chemical Name: 2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane
• CAS No.: 100021-14-5
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.268
• Mol file: 100021-14-5.mol

Synonyms:2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane

Chemical Property of 2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane

There total 2 articles about 2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane 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: 62.0%

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol (100021-11-2) → 2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane (100021-14-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1021/jo00358a023

Reference yield:

5-(benzyloxymethyl)cyclopentadiene (39939-07-6) → 2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane (100021-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: O₂, thiourea, sodium acetate, Rose bengal / methanol / 9 h / -5 °C / Irradiation

2: 62 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 48 h / Ambient temperature

With oxygen; sodium acetate; rose bengal; thiourea; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1021/jo00358a023

Reference yield: 100.0%

2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane (100021-14-5) → (+/-)-(1α,2α,3β,4α,5β)-3-azido-5-<(phenylmethoxy)methyl>-1,2,4-cyclopentanetriol (100021-15-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 110 ℃; for 12h;

DOI:10.1021/jo00358a023

upstream raw materials:

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

5-(benzyloxymethyl)cyclopentadiene

Downstream raw materials:

(+/-)-(1α,2α,3β,4α,5β)-3-azido-5-<(phenylmethoxy)methyl>-1,2,4-cyclopentanetriol

(+/-)-(1α,2α,3β,4α,5β)-3-adenin-9-yl-5-<(phenylmethoxy)methyl>-1,2,4-cyclopentanetriol

2',3'-isopropylidine (+/-) aristeromycin

(-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane

Refernces