(S)-4-((Z)-(R)-7-Acetoxy-1-hydroxy-hept-5-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Base Information

Chemical Name:(S)-4-((Z)-(R)-7-Acetoxy-1-hydroxy-hept-5-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
CAS No.:444687-27-8
Molecular Formula:C₂₂H₃₁NO₆
Molecular Weight:405.491
Hs Code.:

Synonyms:(S)-4-((Z)-(R)-7-Acetoxy-1-hydroxy-hept-5-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Chemical Property of (S)-4-((Z)-(R)-7-Acetoxy-1-hydroxy-hept-5-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

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Technology Process of (S)-4-((Z)-(R)-7-Acetoxy-1-hydroxy-hept-5-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

There total 6 articles about (S)-4-((Z)-(R)-7-Acetoxy-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:

: 75-36-5
acetyl chloride

: 444687-57-4
(S)-4-((Z)-(R)-1,7-Dihydroxy-hept-5-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

: 444687-27-8
(S)-4-((Z)-(R)-7-Acetoxy-1-hydroxy-hept-5-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -15 ℃; for 1h;
DOI:10.1021/ol0261480

Reference yield:

: 117833-92-8
(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde

: 444687-27-8
(S)-4-((Z)-(R)-7-Acetoxy-1-hydroxy-hept-5-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: magnesium; Br(CH₂)2Br / tetrahydrofuran / 3 h / Heating

1.2: 94 percent / tetrahydrofuran / 3 h / -78 - 20 °C

2.1: 85 percent / oxalyl chloride; DMSO; NEt₃ / CH₂Cl₂ / 6.5 h / -78 - 20 °C

3.1: 94 percent / Zn(BH₄)2; CeCl₃*7H₂O / diethyl ether; methanol / 4 h / 0 °C

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

5.1: 8.27 g / 2,6-lutidine / CH₂Cl₂ / 1 h / -15 °C

With 2,6-dimethylpyridine; cerium(III) chloride; zinc(II) tetrahydroborate; oxalyl dichloride; tetrabutyl ammonium fluoride; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.2: Grignard addition / 2.1: Swern oxidation / 3.1: Luche reduction;
DOI:10.1021/ol0261480

Reference yield:

: 98894-85-0
(Z)-6-chlorohex-2-en-1-ol tert-butyldimethylsilyl ether

: 444687-27-8
(S)-4-((Z)-(R)-7-Acetoxy-1-hydroxy-hept-5-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: magnesium; Br(CH₂)2Br / tetrahydrofuran / 3 h / Heating

1.2: 94 percent / tetrahydrofuran / 3 h / -78 - 20 °C

2.1: 85 percent / oxalyl chloride; DMSO; NEt₃ / CH₂Cl₂ / 6.5 h / -78 - 20 °C

3.1: 94 percent / Zn(BH₄)2; CeCl₃*7H₂O / diethyl ether; methanol / 4 h / 0 °C

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

5.1: 8.27 g / 2,6-lutidine / CH₂Cl₂ / 1 h / -15 °C

With 2,6-dimethylpyridine; cerium(III) chloride; zinc(II) tetrahydroborate; oxalyl dichloride; tetrabutyl ammonium fluoride; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.2: Grignard addition / 2.1: Swern oxidation / 3.1: Luche reduction;
DOI:10.1021/ol0261480