(S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester

Base Information

Chemical Name:(S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester
CAS No.:449729-42-4
Molecular Formula:C₂₂H₃₁NO₆S
Molecular Weight:437.557
Hs Code.:

Synonyms:(S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester

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Chemical Property of (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester

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Technology Process of (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester

There total 11 articles about (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl 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: 73.0%

: 77-78-1
dimethyl sulfate

: 449729-39-9
(S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid

: 449729-42-4
(S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 25 ℃;
DOI:10.1016/S0040-4039(02)00537-3

Reference yield:

: 77-78-1
dimethyl sulfate

: (2R,4R)-4-(6-Carboxy-2-oxo-1-trimethylsilanyloxy-hexyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester

: 449729-42-4
(S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester

Guidance literature:: (2R,4R)-4-(6-Carboxy-2-oxo-1-trimethylsilanyloxy-hexyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester; In dibutyl ether; toluene;

dimethyl sulfate; With potassium carbonate; In N,N-dimethyl-formamide; at 10 - 25 ℃; Further stages.;
DOI:10.1021/jo025794+

Reference yield:

: 196930-46-8
(4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid

: 449729-42-4
(S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / SOCl₂ / 17 h / 25 °C

2.1: 100 percent / CaCl₂; NaBH₄ / ethanol / 2 h / -10 - 10 °C

3.1: 88 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 0.5 h / 10 °C

4.1: 95 percent / dimethylsulfoxide; sulfur trioxide pyridine complex; triethylamine / toluene / 2 h / 10 °C

5.1: 100 percent / n-Bu₃P / CH₂Cl₂ / 0.5 h / -10 °C

6.1: Mg / dibutyl ether; toluene / 1.5 h / 40 - 70 °C

6.2: dibutyl ether; toluene / 0.75 h / -30 - -25 °C

6.3: dibutyl ether; toluene / 0.5 h / -30 °C

7.1: 10percent aqueous citric acid / dibutyl ether; toluene

7.2: 37.9 g / K₂CO₃ / dimethylformamide / 10 - 25 °C

With sodium tetrahydroborate; thionyl chloride; tributylphosphine; sulfur trioxide pyridine complex; sodium carbonate; magnesium; dimethyl sulfoxide; triethylamine; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane; dibutyl ether; water; toluene;
DOI:10.1021/jo025794+