(4S,5R)-4-Benzyl-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4S,5R)-4-Benzyl-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 203806-82-0
• Molecular Formula: C₂₁H₃₁NO₄
• Molecular Weight: 361.481
• Mol file: 203806-82-0.mol

Synonyms:

Chemical Property of (4S,5R)-4-Benzyl-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4-Benzyl-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 11 articles about (4S,5R)-4-Benzyl-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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:

phenylmagnesium bromide (100-58-3) → (4S,5R)-4-Benzyl-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (203806-82-0)

Guidance literature:

Multi-step reaction with 10 steps

1: -70 - -40 °C

2: DMAP / Ambient temperature

3: 74 percent / H₂ / ethyl acetate / 40 °C / 5171.5 Torr

4: 1.) CAN

5: 95 percent / Et₃N, DMAP / 20 h / Ambient temperature

6: HF / acetonitrile; pyridine

7: pyridinium-p-toluenesulfonate / toluene / Heating

8: DIBALH / toluene / 2 h / Ambient temperature

9: (COCl)2, Et₃N / dimethylsulfoxide / 1 h / -65 °C

10: BF₃*Et₂O / CH₂Cl₂

With dmap; oxalyl dichloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; In pyridine; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile;

DOI:10.1016/S0040-4039(97)10677-3

Reference yield:

(3R,4S)-4-Benzyl-1-(4-methoxy-phenyl)-3-triisopropylsilanyloxy-azetidin-2-one (203806-59-1) → (4S,5R)-4-Benzyl-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (203806-82-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) CAN

2: 95 percent / Et₃N, DMAP / 20 h / Ambient temperature

3: HF / acetonitrile; pyridine

4: pyridinium-p-toluenesulfonate / toluene / Heating

5: DIBALH / toluene / 2 h / Ambient temperature

6: (COCl)2, Et₃N / dimethylsulfoxide / 1 h / -65 °C

7: BF₃*Et₂O / CH₂Cl₂

With dmap; oxalyl dichloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; hydrogen fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; In pyridine; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile;

DOI:10.1016/S0040-4039(97)10677-3

Reference yield:

(3R,4S)-4-(Hydroxy-phenyl-methyl)-1-(4-methoxy-phenyl)-3-triisopropylsilanyloxy-azetidin-2-one → (4S,5R)-4-Benzyl-5-((S)-1-hydroxy-but-3-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (203806-82-0)

Guidance literature:

Multi-step reaction with 9 steps

1: DMAP / Ambient temperature

2: 74 percent / H₂ / ethyl acetate / 40 °C / 5171.5 Torr

3: 1.) CAN

4: 95 percent / Et₃N, DMAP / 20 h / Ambient temperature

5: HF / acetonitrile; pyridine

6: pyridinium-p-toluenesulfonate / toluene / Heating

7: DIBALH / toluene / 2 h / Ambient temperature

8: (COCl)2, Et₃N / dimethylsulfoxide / 1 h / -65 °C

9: BF₃*Et₂O / CH₂Cl₂

With dmap; oxalyl dichloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; In pyridine; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile;

DOI:10.1016/S0040-4039(97)10677-3

upstream raw materials:

allyltributylstanane

(4S,5S)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-benzyl-5-formyl-1,3-oxazolidine

(2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

(4S,5R)-4-Benzyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester