(4R,5S)-3-{(E)-3-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-acryloyl}-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

Chemical Name:(4R,5S)-3-{(E)-3-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-acryloyl}-4-methyl-5-phenyl-oxazolidin-2-one
CAS No.:168777-85-3
Molecular Formula:C₂₆H₃₉NO₅Si
Molecular Weight:473.685
Hs Code.:

Synonyms:(4R,5S)-3-{(E)-3-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-acryloyl}-4-methyl-5-phenyl-oxazolidin-2-one

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Chemical Property of (4R,5S)-3-{(E)-3-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-acryloyl}-4-methyl-5-phenyl-oxazolidin-2-one

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Technology Process of (4R,5S)-3-{(E)-3-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-acryloyl}-4-methyl-5-phenyl-oxazolidin-2-one

There total 12 articles about (4R,5S)-3-{(E)-3-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-acryloyl}-4-methyl-5-phenyl-oxazolidin-2-one 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%

: 128209-97-2
(1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde

: 147725-15-3
diethyl 2-<(4R,5S)-4-methyl-2-oxo-5-phenyl-3-oxazolidinyl>-2-oxoethanephosphonate

: 168777-85-3
(4R,5S)-3-{(E)-3-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-acryloyl}-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; 1.) 25 deg C, 15 min, 2.) 25 deg C, 6 h;

Reference yield:

: 148933-66-8
((1S,2R,6R)-2-Benzyloxy-6-methoxy-cyclohexyloxy)-tert-butyl-dimethyl-silane

: 168777-85-3
(4R,5S)-3-{(E)-3-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-acryloyl}-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: 98 percent / H₂ / 10percent Pd/C / ethanol / 24 h / 25 °C

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) r.t., 2 h

3: LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) 25 deg C, 2 h

4: Pd(OAc)2 / acetonitrile / 24 h / 50 °C

5: 95 percent / LiBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 1 h / -78 °C

6: 2.) LiEt₃BH / 1.) xylene, reflux, 48 h, 2.) THF, r.t., 2 h

7: 100 percent / H₂ / 10percent Pd/C / ethanol / 16 h / 25 °C

8: 1.) o-O₂NC₆H₄SeCN, n-Bu₃P, 2.) 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 3 h, 2.) THF, 25 deg C, 6 h

9: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) 25 deg C, overnight

10: 95 percent / LiCl, (i-Pr)2NEt / acetonitrile / 1.) 25 deg C, 15 min, 2.) 25 deg C, 6 h

With palladium diacetate; lithium borohydride; ortho-nitrophenyl selenocyanate; cerium(III) chloride; oxalyl dichloride; dimethylsulfide; tributylphosphine; hydrogen; dihydrogen peroxide; lithium triethylborohydride; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; acetonitrile;

Reference yield:

: (1S,2R,6S)-2-(benzyloxy)-7-oxabicyclo[4.1.0]heptane

: 168777-85-3
(4R,5S)-3-{(E)-3-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-acryloyl}-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 12 steps

1: 90 percent / CSA / 2 h / 25 °C

2: 91 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

3: 98 percent / H₂ / 10percent Pd/C / ethanol / 24 h / 25 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) r.t., 2 h

5: LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) 25 deg C, 2 h

6: Pd(OAc)2 / acetonitrile / 24 h / 50 °C

7: 95 percent / LiBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 1 h / -78 °C

8: 2.) LiEt₃BH / 1.) xylene, reflux, 48 h, 2.) THF, r.t., 2 h

9: 100 percent / H₂ / 10percent Pd/C / ethanol / 16 h / 25 °C

10: 1.) o-O₂NC₆H₄SeCN, n-Bu₃P, 2.) 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 3 h, 2.) THF, 25 deg C, 6 h

11: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) 25 deg C, overnight

12: 95 percent / LiCl, (i-Pr)2NEt / acetonitrile / 1.) 25 deg C, 15 min, 2.) 25 deg C, 6 h

With 2,6-dimethylpyridine; palladium diacetate; lithium borohydride; ortho-nitrophenyl selenocyanate; cerium(III) chloride; oxalyl dichloride; dimethylsulfide; tributylphosphine; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; lithium triethylborohydride; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetonitrile;