(2S,3R)-2-Azido-4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-butyric acid ethyl ester

Base Information

• Chemical Name: (2S,3R)-2-Azido-4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-butyric acid ethyl ester
• CAS No.: 217175-19-4
• Molecular Formula: C₂₂H₂₉N₃O₄Si
• Molecular Weight: 427.575

Synonyms:(2S,3R)-2-Azido-4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-butyric acid ethyl ester

Chemical Property of (2S,3R)-2-Azido-4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-butyric acid ethyl ester

Chemical Property:

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Technology Process of (2S,3R)-2-Azido-4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-butyric acid ethyl ester

There total 2 articles about (2S,3R)-2-Azido-4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-butyric acid ethyl 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: 82.0%

(2S,3R)-ethyl 2-azido-3,4-dihydroxybutanoate (101924-56-5) + tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3R)-2-Azido-4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-butyric acid ethyl ester (217175-19-4)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran;

DOI:10.1021/jo9817117

Reference yield:

diethyl (2S,3R)-2-azido-3-hydroxysuccinate (101924-53-2) → (2S,3R)-2-Azido-4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-butyric acid ethyl ester (217175-19-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / BH₃*Me₂S; NaBH₄ / tetrahydrofuran

2: 82 percent / imidazole / tetrahydrofuran

With 1H-imidazole; sodium tetrahydroborate; dimethylsulfide borane complex; In tetrahydrofuran; 1: Reduction / 2: silylation;

DOI:10.1021/jo9817117

Reference yield:

(2S,3R)-2-Azido-4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-butyric acid ethyl ester (217175-19-4) → (2S,3R)-2-Amino-4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-butyric acid ethyl ester

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1021/jo9817117

upstream raw materials:

(2S,3R)-ethyl 2-azido-3,4-dihydroxybutanoate

tert-butylchlorodiphenylsilane

diethyl (2S,3R)-2-azido-3-hydroxysuccinate

Downstream raw materials:

(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(S)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(S)-1-methoxycarbonylmethyl-3-(toluene-4-sulfonylamino)-propyl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(3R,4S)-3-(2-methyl-allyl)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

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