(+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene

Base Information

• Chemical Name: (+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene
• CAS No.: 100021-18-9
• Molecular Formula: C₁₆H₂₀O₃
• Molecular Weight: 260.333
• Mol file: 100021-18-9.mol

Synonyms:(+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene

Chemical Property of (+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene

There total 6 articles about (+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-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: 60.0%

(+/-)-(1β,2α,3α,4β,5α)-2,3-(dimethylmethylenedioxy)-5-<(1-imidazolylthiocarbonyl)oxy>-4-<(phenylmethoxy)methyl>-1-cyclopentyl azide (100021-17-8) → (+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene (100021-18-9)

Guidance literature:

With polymethylhydrogen siloxane; 2,2'-azobis(isobutyronitrile); di(n-butyl)tin oxide; In toluene; for 2h; Heating;

DOI:10.1021/jo00358a023

Reference yield:

5-(benzyloxymethyl)cyclopentadiene (39939-07-6) → (+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene (100021-18-9)

Guidance literature:

Multi-step reaction with 6 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

3: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C

4: 92 percent / 75percent aq. HClO₄ / acetone / 1 h / Ambient temperature

5: 95 percent / dimethylformamide / 5 h / Ambient temperature

6: 60 percent / 2,2'-azobis(2-methylpropionitrile), polymethylhydrogen siloxane, dibutyltin oxide / toluene / 2 h / Heating

With sodium azide; perchloric acid; polymethylhydrogen siloxane; 2,2'-azobis(isobutyronitrile); oxygen; sodium acetate; rose bengal; di(n-butyl)tin oxide; thiourea; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jo00358a023

Reference yield:

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol (100021-11-2) → (+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene (100021-18-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 48 h / Ambient temperature

2: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C

3: 92 percent / 75percent aq. HClO₄ / acetone / 1 h / Ambient temperature

4: 95 percent / dimethylformamide / 5 h / Ambient temperature

5: 60 percent / 2,2'-azobis(2-methylpropionitrile), polymethylhydrogen siloxane, dibutyltin oxide / toluene / 2 h / Heating

With sodium azide; perchloric acid; polymethylhydrogen siloxane; 2,2'-azobis(isobutyronitrile); di(n-butyl)tin oxide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jo00358a023

upstream raw materials:

(+/-)-(1β,2α,3α,4β,5α)-2,3-(dimethylmethylenedioxy)-5-<(1-imidazolylthiocarbonyl)oxy>-4-<(phenylmethoxy)methyl>-1-cyclopentyl azide

5-(benzyloxymethyl)cyclopentadiene

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

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