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100021-18-9

100021-18-9

Identification

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

  • CAS Number: 100021-18-9

  • EINECS:

  • Molecular Weight:260.333

  • Molecular Formula: C16H20O3

  • HS Code:

  • Mol File:100021-18-9.mol

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

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Relevant articles and documentsAll total 1 Articles be found

A Novel and Stereospecific Synthesis of (+/-)- and (-)-Aristeromycin

Madhavan, G. V. Bindu,Martin, John C.

, p. 1287 - 1293 (2007/10/02)

A new, efficient synthetic route to (+/-)- and (-)-aristeromycin (1) has been developed which has as its key feature the cycloaddition of singlet oxygen to 5--1,3-cyclopentadiene (8) followed by in situ reduction to give ene diol 10.This reaction has been optimized and scaled-up to give 197 g (60percent) of partially purified 10.The key intermediate azide 15 was prepared from the partially purified 10 in 56percent yield by a three-step sequence of epoxidation to give 13, reaction with NaN3, and acetonation.Azide 15 was converted by standard chemistry via adenine intermediate 22 to (+/-)-aristeromycin (1) in 31percent overall yield.Intermediate 22 was also prepared in 25percent yield by a novel and shorter sequence which involved the reaction of epoxide 13 with the sodium salt of adenine and then acetonation.Alternatively, azide 15 was resolved by conversion to its naproxen ester 26, and the (-)-isomer of 15 was converted to the known amino triol 31, thus constituting a formal synthesis of (-)-aristeromycin.

Process route upstream and downstream products

Process route

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

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

(+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene
100021-18-9

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

Conditions
Conditions Yield
With polymethylhydrogen siloxane; 2,2'-azobis(isobutyronitrile); di(n-butyl)tin oxide; In toluene; for 2h; Heating;
60%
5-(benzyloxymethyl)cyclopentadiene
39939-07-6

5-(benzyloxymethyl)cyclopentadiene

(+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene
100021-18-9

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

Conditions
Conditions Yield
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;
(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol
100021-11-2

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

(+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene
100021-18-9

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

Conditions
Conditions Yield
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;
2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane
100021-14-5

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

(+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene
100021-18-9

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

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C
2: 92 percent / 75percent aq. HClO4 / acetone / 1 h / Ambient temperature
3: 95 percent / dimethylformamide / 5 h / Ambient temperature
4: 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; In N,N-dimethyl-formamide; acetone; toluene;
(+/-)-(1α,2α,3β,4α,5β)-3-azido-5-<(phenylmethoxy)methyl>-1,2,4-cyclopentanetriol
100021-15-6

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

(+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene
100021-18-9

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

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 92 percent / 75percent aq. HClO4 / acetone / 1 h / Ambient temperature
2: 95 percent / dimethylformamide / 5 h / Ambient temperature
3: 60 percent / 2,2'-azobis(2-methylpropionitrile), polymethylhydrogen siloxane, dibutyltin oxide / toluene / 2 h / Heating
With perchloric acid; polymethylhydrogen siloxane; 2,2'-azobis(isobutyronitrile); di(n-butyl)tin oxide; In N,N-dimethyl-formamide; acetone; toluene;
(+/-)-(1α,2β,3α,4α,5β)-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100021-16-7

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

(+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene
100021-18-9

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

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 95 percent / dimethylformamide / 5 h / Ambient temperature
2: 60 percent / 2,2'-azobis(2-methylpropionitrile), polymethylhydrogen siloxane, dibutyltin oxide / toluene / 2 h / Heating
With polymethylhydrogen siloxane; 2,2'-azobis(isobutyronitrile); di(n-butyl)tin oxide; In N,N-dimethyl-formamide; toluene;
(+/-)-(1β,2α,3α,4β,5α)-2,3-(dimethylmethylenedioxy)-5-<(1-imidazolylthiocarbonyl)oxy>-4-<(phenylmethoxy)methyl>-1-cyclopentyl azide
100021-17-8

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

(+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene
100021-18-9

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

Conditions
Conditions Yield
With polymethylhydrogen siloxane; 2,2'-azobis(isobutyronitrile); di(n-butyl)tin oxide; In toluene; for 2h; Heating;
60%
5-(benzyloxymethyl)cyclopentadiene
39939-07-6

5-(benzyloxymethyl)cyclopentadiene

(+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene
100021-18-9

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

Conditions
Conditions Yield
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;
(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol
100021-11-2

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

(+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene
100021-18-9

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

Conditions
Conditions Yield
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;
2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane
100021-14-5

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

(+/-)-(1β,2α,3α)-2,3-(dimethylmethylenedioxy)-1-<(phenylmethoxy)methyl>-4-cyclopentene
100021-18-9

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

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 100 percent / sodium azide / dimethylformamide / 12 h / 110 °C
2: 92 percent / 75percent aq. HClO4 / acetone / 1 h / Ambient temperature
3: 95 percent / dimethylformamide / 5 h / Ambient temperature
4: 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; In N,N-dimethyl-formamide; acetone; toluene;

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