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

Base Information

Chemical Name:(-)-(1R,2R,4S)-2-<(Benzyloxy)methyl>-4-<(2-methoxyethoxy)methoxy>-1-cyclopentanecarboxaldehyde
CAS No.:149706-72-9
Molecular Formula:C₁₈H₂₆O₅
Molecular Weight:322.401
Hs Code.:

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

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

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

There total 13 articles about (-)-(1R,2R,4S)-2-<(Benzyloxy)methyl>-4-<(2-methoxyethoxy)methoxy>-1-cyclopentanecarboxaldehyde 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: 90.0%

: 149706-71-8
(+)-(1R,3R,4R)-1-<(2-Methoxyethoxy)methoxy>-3-(hydroxymethyl)-4-<(benzyloxy)methyl>cyclopentane

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

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jo00069a013

Reference yield:

: 100-52-7
benzaldehyde

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

Guidance literature:: Multi-step reaction with 13 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

With 1H-imidazole; dmap; sodium chlorite; sodium periodate; 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

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

Guidance literature:: Multi-step reaction with 11 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

With 1H-imidazole; dmap; sodium chlorite; sodium periodate; 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