(S)-3-{(R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-2-oxo-ethyl]-oxiranyl}-butyric acid benzyl ester

Base Information

• Chemical Name: (S)-3-{(R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-2-oxo-ethyl]-oxiranyl}-butyric acid benzyl ester
• CAS No.: 205369-36-4
• Molecular Formula: C₂₂H₃₄O₅Si
• Molecular Weight: 406.594
• Mol file: 205369-36-4.mol

Synonyms:(S)-3-{(R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-2-oxo-ethyl]-oxiranyl}-butyric acid benzyl ester

Chemical Property of (S)-3-{(R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-2-oxo-ethyl]-oxiranyl}-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-{(R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-2-oxo-ethyl]-oxiranyl}-butyric acid benzyl ester

There total 11 articles about (S)-3-{(R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-2-oxo-ethyl]-oxiranyl}-butyric acid benzyl ester 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:

tert-Butyl-{(S)-1-[(R)-2-((E)-(S)-5-methoxy-1,5-dimethyl-hex-3-enyl)-oxiranyl]-1-methyl-allyloxy}-dimethyl-silane (205369-35-3) + benzyl alcohol (100-51-6,185532-71-2) → (S)-3-{(R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-2-oxo-ethyl]-oxiranyl}-butyric acid benzyl ester (205369-36-4)

Guidance literature:

With sodium hydrogencarbonate; ozone; triethylamine; trifluoroacetic anhydride; In dichloromethane; at -78 ℃;

DOI:10.1039/a800011e

Reference yield:

(S)-Citronellal (5949-05-3) → (S)-3-{(R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-2-oxo-ethyl]-oxiranyl}-butyric acid benzyl ester (205369-36-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 94 percent / LDA, MeI, NaHCO₃

2: 93 percent / NaBH₄, CeCl₃*7H₂O

3: NaHCO₃ / tetrahydrofuran

4: aq. H₂O₂, NaHCO₃ / tetrahydrofuran

5: t-BuOOH, Ti(O-i-Pr)4, (+)-DIPT / CH₂Cl₂

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂

7: 72 percent / tetrahydrofuran / -78 °C

8: 100 percent / Dess-Martin periodinane

9: 60 percent / diethyl ether / -78 °C

10: 76 percent / 2,6-lutidine / CH₂Cl₂ / -35 °C

11: O₃, (CF₃CO)2O, NaHCO₃, Et₃N / CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; L-(+)-diisopropyl tartrate; dihydrogen peroxide; sodium hydrogencarbonate; Dess-Martin periodane; ozone; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; lithium diisopropyl amide; methyl iodide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1039/a800011e

Reference yield:

(3S)-α-methylene-3,7-dimethyl-6-octen-1-al (141608-97-1) → (S)-3-{(R)-2-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-2-oxo-ethyl]-oxiranyl}-butyric acid benzyl ester (205369-36-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / NaBH₄, CeCl₃*7H₂O

2: NaHCO₃ / tetrahydrofuran

3: aq. H₂O₂, NaHCO₃ / tetrahydrofuran

4: t-BuOOH, Ti(O-i-Pr)4, (+)-DIPT / CH₂Cl₂

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂

6: 72 percent / tetrahydrofuran / -78 °C

7: 100 percent / Dess-Martin periodinane

8: 60 percent / diethyl ether / -78 °C

9: 76 percent / 2,6-lutidine / CH₂Cl₂ / -35 °C

10: O₃, (CF₃CO)2O, NaHCO₃, Et₃N / CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; L-(+)-diisopropyl tartrate; dihydrogen peroxide; sodium hydrogencarbonate; Dess-Martin periodane; ozone; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1039/a800011e

upstream raw materials:

tert-Butyl-{(S)-1-[(R)-2-((E)-(S)-5-methoxy-1,5-dimethyl-hex-3-enyl)-oxiranyl]-1-methyl-allyloxy}-dimethyl-silane

benzyl alcohol

(S)-Citronellal

(3S)-α-methylene-3,7-dimethyl-6-octen-1-al

Downstream raw materials:

(S)-3-[(R)-2-((R)-1-Hydroxy-1-methoxycarbonyl-ethyl)-oxiranyl]-butyric acid benzyl ester