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Cas Database

100101-50-6

100101-50-6

Identification

  • Product Name:<1S-(1α,2β,3α,4α,5β)>-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol

  • CAS Number: 100101-50-6

  • EINECS:

  • Molecular Weight:319.36

  • Molecular Formula: C16H21N3O4

  • HS Code:

  • Mol File:100101-50-6.mol

Synonyms:<1S-(1α,2β,3α,4α,5β)>-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol

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Relevant articles and documentsAll total 5 Articles be found

Chiral syntheses of 6′-β-fluoroaristeromycin, 6′-β-fluoro-5′-noraristeromycin and aristeromycin

Yin, Xue-Qiang,Schneller, Stewart W.

, p. 7535 - 7538 (2007/10/03)

Carbocyclic nucleosides substituted at the C-6′ position are receiving increasing attention. Chiral synthetic accessibility to the biologically promising 6′-β-fluoroaristeromycin is lacking. Its preparation and that of the 5′-nor analogue are described. A

Enzyme-catalysed Hydrolysis of 3,5-cis-Diacetoxy-4-trans-benzyloxymethylcyclopentene and the Synthesis of Aristeromycin Precursors

LeGrand, Darren M.,Roberts, Stanley M.

, p. 1751 - 1752 (2007/10/02)

The optically active mono-ester 2 was obtained by enzyme-catalysed hydrolysis of the diester 1 and converted into the azide 8 and the amine 13, synthetic precursors of (+)- and (-)-aristeromycin.

Enzyme-Catalysed Hydrolyses of Some Meso-Diesters

Cotterill, Ian C.,Cox, Philip B.,Drake, Alex F.,Grand, Darren M. Le,Hutchinson, Edward J.,et al.

, p. 3071 - 3076 (2007/10/02)

The diester 7 is hydrolysed, using porcine pancreatic lipase as catalyst, to give the monoester 8.The latter compound has been converted into the known azido alcohol 9 and into the purine derivative 10.Pig liver esterase (ple) catalysed hydrolysis of the diester 11 gave the acid 13 not the enantiomer 12 as previously reported.The structure of 13 was determined by its conversion into the compound ent-10.The diesters 17 and 18 are converted into the mono-esters 20 and 21 respectively using ple: hydrolysis of the diester 16 yields a mono-acid of high optical purity.The structure of this mono-acid is believed to be that shown in formula 19.

Purinyl or pyrimidinyl substituted hydroxycyclopentane compounds useful as antivirals

-

, (2008/06/13)

Novel 4-substituted-5-hydroxymethyl-1,2-cyclopentanediols or 1-cyclopentanol substituted at the 3-position by various heterocyclic groups are useful as antiviral agents.

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

<1S-(1β,2α,3α,4β,5α)>-2,3-(dimethylmethylenedioxy)-5-<(S)-(2-(6-methoxy-2-naphthyl)propionyl)oxy>-4-<(phenylmethoxy)methyl>-1-cyclopentyl azide
100021-25-8

<1S-(1β,2α,3α,4β,5α)>-2,3-(dimethylmethylenedioxy)-5-<(S)-(2-(6-methoxy-2-naphthyl)propionyl)oxy>-4-<(phenylmethoxy)methyl>-1-cyclopentyl azide

<1S-(1α,2β,3α,4α,5β)>-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100101-50-6

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

Conditions
Conditions Yield
With sodium hydroxide; In tetrahydrofuran; for 4h; Heating;
91%
(3aS,4R,5S,6S,6aR)-4-Azido-6-benzyloxymethyl-5-(2-methoxy-ethoxymethoxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

(3aS,4R,5S,6S,6aR)-4-Azido-6-benzyloxymethyl-5-(2-methoxy-ethoxymethoxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

<1S-(1α,2β,3α,4α,5β)>-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100101-50-6

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

Conditions
Conditions Yield
With dimethylboron bromide; In diethyl ether; dichloromethane; at -78 ℃; for 2h;
75%
5-(benzyloxymethyl)cyclopentadiene
39939-07-6

5-(benzyloxymethyl)cyclopentadiene

<1S-(1α,2β,3α,4α,5β)>-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100101-50-6

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

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: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
6: 91 percent / NaOH / tetrahydrofuran / 4 h / Heating
With pyridine; dmap; sodium hydroxide; sodium azide; perchloric acid; oxygen; sodium acetate; rose bengal; thiourea; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
(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

<1S-(1α,2β,3α,4α,5β)>-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100101-50-6

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

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: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
5: 91 percent / NaOH / tetrahydrofuran / 4 h / Heating
With pyridine; dmap; sodium hydroxide; sodium azide; perchloric acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane
100021-14-5

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

<1S-(1α,2β,3α,4α,5β)>-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100101-50-6

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

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: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
4: 91 percent / NaOH / tetrahydrofuran / 4 h / Heating
With pyridine; dmap; sodium hydroxide; sodium azide; perchloric acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
(+/-)-(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

<1S-(1α,2β,3α,4α,5β)>-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100101-50-6

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

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 92 percent / 75percent aq. HClO4 / acetone / 1 h / Ambient temperature
2: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
3: 91 percent / NaOH / tetrahydrofuran / 4 h / Heating
With pyridine; dmap; sodium hydroxide; perchloric acid; In tetrahydrofuran; dichloromethane; acetone;
(+/-)-(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

<1S-(1α,2β,3α,4α,5β)>-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100101-50-6

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

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
2: 91 percent / NaOH / tetrahydrofuran / 4 h / Heating
With pyridine; dmap; sodium hydroxide; In tetrahydrofuran; dichloromethane;
(2R,3R,4R)-4-Benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane-2,3-diol

(2R,3R,4R)-4-Benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane-2,3-diol

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

(3aS,4S,5R,6R,6aR)-5-Azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

(3aS,4S,5R,6R,6aR)-5-Azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

<1S-(1α,2β,3α,4α,5β)>-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100101-50-6

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

Conditions
Conditions Yield
(2R,3R,4R)-4-Benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane-2,3-diol; With sodium azide; In water; N,N-dimethyl-formamide;
2,2-dimethoxy-propane; With toluene-4-sulfonic acid; In acetone;
(1R,2S,3S,4S,5R)-3-Azido-5-benzyloxymethyl-4-(2-methoxy-ethoxymethoxy)-cyclopentane-1,2-diol
143994-99-4

(1R,2S,3S,4S,5R)-3-Azido-5-benzyloxymethyl-4-(2-methoxy-ethoxymethoxy)-cyclopentane-1,2-diol

<1S-(1α,2β,3α,4α,5β)>-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100101-50-6

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

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 92 percent / p-TsOH / 2 h
2: 75 percent / Me2BBr / CH2Cl2; diethyl ether / 2 h / -78 °C
With dimethylboron bromide; toluene-4-sulfonic acid; In diethyl ether; dichloromethane;
(1α,2β,3α)-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol diacetate
134756-61-9

(1α,2β,3α)-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol diacetate

<1S-(1α,2β,3α,4α,5β)>-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol
100101-50-6

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

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 96 percent / 168 h / Ambient temperature; porcine pancreatic lipase, phosphate buffer, pH 7
2: 1.) m-chloroperoxybenzoic acid, 2.) i-Pr2NEt / 1.) CH2Cl2, 0 deg C to r.t., 24 h, 2.) CH2Cl2, r.t., 48 h
With N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid;

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