(S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-hept-5-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-hept-5-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
• CAS No.: 444687-22-3
• Molecular Formula: C₂₆H₄₃NO₅Si
• Molecular Weight: 477.717
• Mol file: 444687-22-3.mol

Synonyms:(S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-hept-5-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property of (S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-hept-5-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-hept-5-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

There total 1 articles about (S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-hept-5-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic 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: 94.0%

(Z)-6-chlorohex-2-en-1-ol tert-butyldimethylsilyl ether (98894-85-0) + (4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde (117833-92-8) → (S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-hept-5-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (444687-22-3)

Guidance literature:

(Z)-6-chlorohex-2-en-1-ol tert-butyldimethylsilyl ether; With magnesium; ethylene dibromide; In tetrahydrofuran; for 3h; Heating;

(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde; In tetrahydrofuran; at -78 - 20 ℃; for 3h; Further stages.;

DOI:10.1021/ol0261480

Reference yield: 85.0%

(S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-hept-5-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (444687-22-3) → (S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-5-enoyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (444687-55-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 6.5h;

DOI:10.1021/ol0261480

Reference yield:

(S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-hept-5-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (444687-22-3) → C50H89N3O12Si3

Guidance literature:

Multi-step reaction with 15 steps

1.1: 85 percent / oxalyl chloride; DMSO; NEt₃ / CH₂Cl₂ / 6.5 h / -78 - 20 °C

2.1: 94 percent / Zn(BH₄)2; CeCl₃*7H₂O / diethyl ether; methanol / 4 h / 0 °C

3.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4.1: 8.27 g / 2,6-lutidine / CH₂Cl₂ / 1 h / -15 °C

5.1: 96 percent / Pd₂(dba)3*CHCl₃; (S,S)-1,2-di[2'-(diphenylphosphino)benzamido]cyclohexane / tetrahydrofuran; diethyl ether / 12 h / 20 °C

6.1: ozone / CH₂Cl₂ / -78 °C

6.2: triphenylphosphine / CH₂Cl₂ / 4 h / cooling

7.1: 5.47 g / sodium hypochlorite; NaH₂PO₄*H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

8.1: 83 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 18 h / 20 °C

9.1: 98 percent / camphorsulfonic acid / methanol; tetrahydrofuran / 12 h / 50 °C

10.1: 90 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

11.1: 100 percent / hydrogen / Pd/C / ethyl acetate; methanol / 12 h

12.1: 81 percent / diisopropylcarbodiimide; 1-hydroxybenzotriazole / CH₂Cl₂; dimethylformamide / 24 h / 20 °C

13.1: hydrogen / Pd/C / ethyl acetate; methanol / 12 h

14.1: 0.162 g / diisopropylcarbodiimide; 1-hydroxybenzotriazole / CH₂Cl₂; dimethylformamide / 48 h / 20 °C

15.1: lithium hydroxide / H₂O; tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; lithium hydroxide; sodium hypochlorite; sodium dihydrogenphosphate; cerium(III) chloride; zinc(II) tetrahydroborate; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; benzotriazol-1-ol; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1.1: Swern oxidation / 2.1: Luche reduction;

DOI:10.1021/ol0261480

upstream raw materials:

(Z)-6-chlorohex-2-en-1-ol tert-butyldimethylsilyl ether

(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde

Downstream raw materials:

(S)-4-[(Z)-7-(tert-Butyl-dimethyl-silanyloxy)-hept-5-enoyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

(S)-2,2-Dimethyl-4-((2R,6S)-6-vinyl-tetrahydro-pyran-2-yl)-oxazolidine-3-carboxylic acid benzyl ester

(2S,6R)-6-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-tetrahydro-pyran-2-carboxylic acid ethyl ester

(S)-4-((2R,6S)-6-Carboxy-tetrahydro-pyran-2-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester