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Cas Database

100021-25-8

100021-25-8

Identification

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

  • CAS Number: 100021-25-8

  • EINECS:

  • Molecular Weight:531.609

  • Molecular Formula:C30H33N3O6

  • HS Code:

  • Mol File:100021-25-8.mol

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

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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

    5-(benzyloxymethyl)cyclopentadiene
    39939-07-6

    5-(benzyloxymethyl)cyclopentadiene

    <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

    Conditions
    ConditionsYield
    Multi-step reaction with 5 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
    With pyridine; dmap; sodium azide; perchloric acid; oxygen; sodium acetate; rose bengal; thiourea; 3-chloro-benzenecarboperoxoic acid;Inmethanol; 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-(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

    Conditions
    ConditionsYield
    Multi-step reaction with 4 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
    With pyridine; dmap; sodium azide; perchloric acid; 3-chloro-benzenecarboperoxoic acid;Indichloromethane; N,N-dimethyl-formamide; acetone;
    (2S)-2-(6-methoxy(2-naphthyl))propanoic acid
    22204-53-1

    (2S)-2-(6-methoxy(2-naphthyl))propanoic acid

    <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

    Conditions
    ConditionsYield
    Multi-step reaction with 2 steps
    1: oxalyl chloride / benzene; dimethylformamide / 1 h / Ambient temperature
    2: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
    With pyridine; dmap; oxalyl dichloride;Indichloromethane; N,N-dimethyl-formamide; benzene;
    2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane
    100021-14-5

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

    <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

    Conditions
    ConditionsYield
    Multi-step reaction with 3 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
    With pyridine; dmap; sodium azide; perchloric acid;Indichloromethane; 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-(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

    Conditions
    ConditionsYield
    Multi-step reaction with 2 steps
    1: 92 percent / 75percent aq. HClO4 / acetone / 1 h / Ambient temperature
    2: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
    With pyridine; dmap; perchloric acid;Indichloromethane; acetone;
    (S)-naproxenoyl chloride
    51091-84-0

    (S)-naproxenoyl chloride

    (+/-)-(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-(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

    (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester
    100101-49-3

    (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,4S,5R,6R,6aS)-4-azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl ester

    Conditions
    ConditionsYield
    With pyridine; dmap;Indichloromethane;for 2h; Yield given. Yields of byproduct given; Ambient temperature;
    5-(benzyloxymethyl)cyclopentadiene
    39939-07-6

    5-(benzyloxymethyl)cyclopentadiene

    <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

    Conditions
    ConditionsYield
    Multi-step reaction with 5 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
    With pyridine; dmap; sodium azide; perchloric acid; oxygen; sodium acetate; rose bengal; thiourea; 3-chloro-benzenecarboperoxoic acid;Inmethanol; 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-(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

    Conditions
    ConditionsYield
    Multi-step reaction with 4 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
    With pyridine; dmap; sodium azide; perchloric acid; 3-chloro-benzenecarboperoxoic acid;Indichloromethane; N,N-dimethyl-formamide; acetone;
    (2S)-2-(6-methoxy(2-naphthyl))propanoic acid
    22204-53-1

    (2S)-2-(6-methoxy(2-naphthyl))propanoic acid

    <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

    Conditions
    ConditionsYield
    Multi-step reaction with 2 steps
    1: oxalyl chloride / benzene; dimethylformamide / 1 h / Ambient temperature
    2: pyridine, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
    With pyridine; dmap; oxalyl dichloride;Indichloromethane; N,N-dimethyl-formamide; benzene;
    2β-benzyloxymethyl-1α,3α-dihydroxy-4α,5α-epoxycyclopentane
    100021-14-5

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

    <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

    Conditions
    ConditionsYield
    Multi-step reaction with 3 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
    With pyridine; dmap; sodium azide; perchloric acid;Indichloromethane; N,N-dimethyl-formamide; acetone;

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