(-)-(4S,1'R,2'R,4'S)-2,2-Dimethyl-4-<2'-<(benzyloxy)methyl>-4'-<(2-methoxyethoxy)methoxy>-1'-cyclopentyl>-1,3-dioxolane

Base Information

Chemical Name:(-)-(4S,1'R,2'R,4'S)-2,2-Dimethyl-4-<2'-<(benzyloxy)methyl>-4'-<(2-methoxyethoxy)methoxy>-1'-cyclopentyl>-1,3-dioxolane
CAS No.:149706-79-6
Molecular Formula:C₂₂H₃₄O₆
Molecular Weight:394.508
Hs Code.:

Synonyms:(-)-(4S,1'R,2'R,4'S)-2,2-Dimethyl-4-<2'-<(benzyloxy)methyl>-4'-<(2-methoxyethoxy)methoxy>-1'-cyclopentyl>-1,3-dioxolane

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Chemical Property of (-)-(4S,1'R,2'R,4'S)-2,2-Dimethyl-4-<2'-<(benzyloxy)methyl>-4'-<(2-methoxyethoxy)methoxy>-1'-cyclopentyl>-1,3-dioxolane

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Technology Process of (-)-(4S,1'R,2'R,4'S)-2,2-Dimethyl-4-<2'-<(benzyloxy)methyl>-4'-<(2-methoxyethoxy)methoxy>-1'-cyclopentyl>-1,3-dioxolane

There total 19 articles about (-)-(4S,1'R,2'R,4'S)-2,2-Dimethyl-4-<2'-<(benzyloxy)methyl>-4'-<(2-methoxyethoxy)methoxy>-1'-cyclopentyl>-1,3-dioxolane 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: 95.0%

: 149706-78-5
(+)-(2S,1'R,2'R,4'S)-1-<2'-<(Benzyloxy)methyl>-4'-<(2-methoxyethoxy)methoxy>-1'-cyclopentyl>-2-hydroxyethanol

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

: 149706-79-6
(-)-(4S,1'R,2'R,4'S)-2,2-Dimethyl-4-<2'-<(benzyloxy)methyl>-4'-<(2-methoxyethoxy)methoxy>-1'-cyclopentyl>-1,3-dioxolane

Guidance literature:: With toluene-4-sulfonic acid; In acetone; for 1.5h;
DOI:10.1021/jo00069a013

Reference yield:

: 100-52-7
benzaldehyde

: 149706-79-6
(-)-(4S,1'R,2'R,4'S)-2,2-Dimethyl-4-<2'-<(benzyloxy)methyl>-4'-<(2-methoxyethoxy)methoxy>-1'-cyclopentyl>-1,3-dioxolane

Guidance literature:: Multi-step reaction with 20 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

15: 94 percent / diethyl ether

16: 99 percent / 1.) LDA / hexane; tetrahydrofuran / 1.) -40 deg C, 30 min, 2.) -78 deg C, 1 h

17: 100 percent / DIBAL / toluene; tetrahydrofuran / 1 h / -78 °C

18: 91 percent / AcONa / 5 h / Heating

19: 87 percent / LiBH₄ / tetrahydrofuran / 12 h / Ambient temperature

20: 95 percent / TsOH / acetone / 1.5 h

With 1H-imidazole; dmap; sodium chlorite; sodium periodate; disodium hydrogenphosphate; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium borohydride; oxalyl dichloride; trimethylamine-N-oxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; sodium acetate; pyridinium p-toluenesulfonate; acetic anhydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; 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

: 149706-79-6
(-)-(4S,1'R,2'R,4'S)-2,2-Dimethyl-4-<2'-<(benzyloxy)methyl>-4'-<(2-methoxyethoxy)methoxy>-1'-cyclopentyl>-1,3-dioxolane

Guidance literature:: Multi-step reaction with 18 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

13: 94 percent / diethyl ether

14: 99 percent / 1.) LDA / hexane; tetrahydrofuran / 1.) -40 deg C, 30 min, 2.) -78 deg C, 1 h

15: 100 percent / DIBAL / toluene; tetrahydrofuran / 1 h / -78 °C

16: 91 percent / AcONa / 5 h / Heating

17: 87 percent / LiBH₄ / tetrahydrofuran / 12 h / Ambient temperature

18: 95 percent / TsOH / acetone / 1.5 h

With 1H-imidazole; dmap; sodium chlorite; sodium periodate; disodium hydrogenphosphate; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium borohydride; oxalyl dichloride; trimethylamine-N-oxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; sodium acetate; acetic anhydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/jo00069a013