(-)-(1R,2R,4S)-2-<(Benzyloxy)methyl>-4-<(2-methoxyethoxy)methoxy>-1-cyclopentanecarboxylic acid

Base Information

Chemical Name:(-)-(1R,2R,4S)-2-<(Benzyloxy)methyl>-4-<(2-methoxyethoxy)methoxy>-1-cyclopentanecarboxylic acid
CAS No.:149706-73-0
Molecular Formula:C₁₈H₂₆O₆
Molecular Weight:338.401
Hs Code.:

Synonyms:(-)-(1R,2R,4S)-2-<(Benzyloxy)methyl>-4-<(2-methoxyethoxy)methoxy>-1-cyclopentanecarboxylic acid

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Chemical Property of (-)-(1R,2R,4S)-2-<(Benzyloxy)methyl>-4-<(2-methoxyethoxy)methoxy>-1-cyclopentanecarboxylic acid

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Technology Process of (-)-(1R,2R,4S)-2-<(Benzyloxy)methyl>-4-<(2-methoxyethoxy)methoxy>-1-cyclopentanecarboxylic acid

There total 14 articles about (-)-(1R,2R,4S)-2-<(Benzyloxy)methyl>-4-<(2-methoxyethoxy)methoxy>-1-cyclopentanecarboxylic acid 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: 100.0%

: 149706-72-9
(-)-(1R,2R,4S)-2-<(Benzyloxy)methyl>-4-<(2-methoxyethoxy)methoxy>-1-cyclopentanecarboxaldehyde

: 149706-73-0
(-)-(1R,2R,4S)-2-<(Benzyloxy)methyl>-4-<(2-methoxyethoxy)methoxy>-1-cyclopentanecarboxylic acid

Guidance literature:: With sodium chlorite; disodium hydrogenphosphate; dihydrogen peroxide; In acetonitrile; for 2h; Ambient temperature;
DOI:10.1021/jo00069a013

Reference yield:

: 100-52-7
benzaldehyde

: 149706-73-0
(-)-(1R,2R,4S)-2-<(Benzyloxy)methyl>-4-<(2-methoxyethoxy)methoxy>-1-cyclopentanecarboxylic acid

Guidance literature:: Multi-step reaction with 14 steps

1: 98 percent / pyridinium p-toluenesulfonate / benzene / 2 h / Heating

2: 99 percent / DIBAL / toluene / 2 h / 0 °C

3: 100 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

4: OsO₄, Me₃N(O) / CCl₄; CH₂Cl₂ / 6 h / Ambient temperature

5: aq. NaIO₄ / tetrahydrofuran / 2 h

6: 30percent aq. H₂O₂, NaH₂PO₄, NaClO₂ / acetonitrile / 12 h / Ambient temperature

7: 91 percent / AcONa, Ac₂O / 1 h / Heating

8: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.) 0 deg C, 0.5 h, 2.) r.t., 1.5 h

9: 75 percent / Me₄NHB(OAc)3, AcOH / acetone; acetonitrile / 72 h / Ambient temperature

10: 78 percent / Et₃N, DMAP / tetrahydrofuran / 3 h / Ambient temperature

11: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / Ambient temperature

12: 100 percent / CH₃ONa / benzene; methanol / 1.) 0 deg C, 1 h, 2.) r.t., 5 h

13: 90 percent / (COCl)2, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

14: 100 percent / 30percent aq. H₂O₂, Na₂HPO₄, NaClO₂ / acetonitrile / 2 h / Ambient temperature

With 1H-imidazole; dmap; sodium chlorite; sodium periodate; disodium hydrogenphosphate; sodium dihydrogenphosphate; osmium(VIII) oxide; oxalyl dichloride; trimethylamine-N-oxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; sodium acetate; pyridinium p-toluenesulfonate; acetic anhydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/jo00069a013

Reference yield:

: 149818-36-0
(-)-(1R,2R)-1-(Hydroxymethyl)-2-<(benzyloxy)methyl>cyclohex-4-ene

: 149706-73-0
(-)-(1R,2R,4S)-2-<(Benzyloxy)methyl>-4-<(2-methoxyethoxy)methoxy>-1-cyclopentanecarboxylic acid

Guidance literature:: Multi-step reaction with 12 steps

1: 100 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: OsO₄, Me₃N(O) / CCl₄; CH₂Cl₂ / 6 h / Ambient temperature

3: aq. NaIO₄ / tetrahydrofuran / 2 h

4: 30percent aq. H₂O₂, NaH₂PO₄, NaClO₂ / acetonitrile / 12 h / Ambient temperature

5: 91 percent / AcONa, Ac₂O / 1 h / Heating

6: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.) 0 deg C, 0.5 h, 2.) r.t., 1.5 h

7: 75 percent / Me₄NHB(OAc)3, AcOH / acetone; acetonitrile / 72 h / Ambient temperature

8: 78 percent / Et₃N, DMAP / tetrahydrofuran / 3 h / Ambient temperature

9: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / Ambient temperature

10: 100 percent / CH₃ONa / benzene; methanol / 1.) 0 deg C, 1 h, 2.) r.t., 5 h

11: 90 percent / (COCl)2, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

12: 100 percent / 30percent aq. H₂O₂, Na₂HPO₄, NaClO₂ / acetonitrile / 2 h / Ambient temperature

With 1H-imidazole; dmap; sodium chlorite; sodium periodate; disodium hydrogenphosphate; sodium dihydrogenphosphate; osmium(VIII) oxide; oxalyl dichloride; trimethylamine-N-oxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; sodium acetate; acetic anhydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;
DOI:10.1021/jo00069a013