(2R,3R)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate

Base Information

• Chemical Name: (2R,3R)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate
• CAS No.: 104241-27-2
• Molecular Formula: C₂₃H₃₉NO₆Si
• Molecular Weight: 453.651

Synonyms:(2R,3R)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate

Chemical Property of (2R,3R)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate

There total 5 articles about (2R,3R)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate 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: 65.0%

(2R,3S)-2-(tert-butoxycarbonyl)amino-3,4-epoxybutyl acetate (97322-35-5) → (2R,3R)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate (104241-27-2)

Guidance literature:

In tetrahydrofuran; 1) -78 deg C, 2 h, 2) 0 deg C, 3 h;

DOI:10.1021/ja00279a064

Reference yield:

4-bromo-phenol (106-41-2) → (2R,3R)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate (104241-27-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / imidazole / dimethylformamide / 1) 0 deg C, 1 h, 2) RT, 30 min

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)87959-X

Reference yield:

tert-butyl [(1S)-1-(hydroxymethyl)prop-2-en-1-yl]carbamate (91103-37-6) → (2R,3R)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate (104241-27-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 17 h / Ambient temperature

2: 82 percent / NEt₃ / tetrahydrofuran / 1 h / 0 °C

With triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(01)87959-X

upstream raw materials:

(2R,3S)-2-(tert-butoxycarbonyl)amino-3,4-epoxybutyl acetate

4-bromo-phenol

tert-butyl [(1S)-1-(hydroxymethyl)prop-2-en-1-yl]carbamate

tert-butyldimethylsilyl chloride

Downstream raw materials:

N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline amide

N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

(2S,3R)-2-(tert-butoxycarbonyl)amino-3-(tetrahydropyranyl)oxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyric acid 2-pyridyl thiolester

(2R,3R)-2-(tert-butoxycarbonyl)amino-3-(tetrahydropyranyl)oxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutanol

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