(2R,3S)-2-[(S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionylamino]-3-hydroxy-butyric acid methyl ester

Base Information

• Chemical Name: (2R,3S)-2-[(S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionylamino]-3-hydroxy-butyric acid methyl ester
• CAS No.: 168553-66-0
• Molecular Formula: C₂₁H₃₆N₂O₇SSi
• Molecular Weight: 488.678
• Mol file: 168553-66-0.mol

Synonyms:(2R,3S)-2-[(S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionylamino]-3-hydroxy-butyric acid methyl ester

Chemical Property of (2R,3S)-2-[(S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionylamino]-3-hydroxy-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-[(S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionylamino]-3-hydroxy-butyric acid methyl ester

There total 6 articles about (2R,3S)-2-[(S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionylamino]-3-hydroxy-butyric 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: 82.0%

(2R,3S)-2-amino-3-hydroxy-butyric acid methyl ester hydrochloride (60538-15-0) + (S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionic acid (168553-64-8) → (2R,3S)-2-[(S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionylamino]-3-hydroxy-butyric acid methyl ester (168553-66-0)

Guidance literature:

With dmap; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; for 12h;

DOI:10.1016/0040-4039(95)00621-I

Reference yield:

2-trimethylsilanyl-ethanesulfonyl chloride (106018-85-3) → (2R,3S)-2-[(S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionylamino]-3-hydroxy-butyric acid methyl ester (168553-66-0)

Guidance literature:

Multi-step reaction with 5 steps

1: NEt₃

2: NaH / dioxane

3: TsOH / methanol

4: 1) Py-SO₃, Et₃N, 2) NaClO₂, NaH₂PO₄ / 1) DMSO, CH₂Cl₂, 2) THF, H₂O

5: DMAP, bromotripyrrolidinophosphonium hexafluorophosphate

With dmap; sodium chlorite; sodium dihydrogenphosphate; sulfur trioxide pyridine complex; sodium hydride; toluene-4-sulfonic acid; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In 1,4-dioxane; methanol;

DOI:10.1055/s-1997-681

Reference yield:

(S)-2-methyl-1-(2-trimethylsilanyl-ethanesulfonyl)-2trityloxymethyl-aziridine (168553-71-7) → (2R,3S)-2-[(S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionylamino]-3-hydroxy-butyric acid methyl ester (168553-66-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / dioxane

2: TsOH / methanol

3: 1) Py-SO₃, Et₃N, 2) NaClO₂, NaH₂PO₄ / 1) DMSO, CH₂Cl₂, 2) THF, H₂O

4: DMAP, bromotripyrrolidinophosphonium hexafluorophosphate

With dmap; sodium chlorite; sodium dihydrogenphosphate; sulfur trioxide pyridine complex; sodium hydride; toluene-4-sulfonic acid; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In 1,4-dioxane; methanol;

DOI:10.1055/s-1997-681

upstream raw materials:

(2R,3S)-2-amino-3-hydroxy-butyric acid methyl ester hydrochloride

(S)-3-Benzyloxy-2-methyl-2-(2-trimethylsilanyl-ethanesulfonylamino)-propionic acid

D-threonine methyl ester

2-trimethylsilanyl-ethanesulfonyl chloride

Downstream raw materials:

2-((S)-1-Amino-2-benzyloxy-1-methyl-ethyl)-5-methyl-oxazole-4-carboxylic acid methylamide

2-[(S)-1-((S)-2-Amino-3-benzyloxy-2-methyl-propionylamino)-2-benzyloxy-1-methyl-ethyl]-5-methyl-oxazole-4-carboxylic acid methylamide

2-<(1S)-2-(Benzyloxy)-1-<<(2S)-3-(benzyloxy)-2-methyl-2-<<<2-(trimethylsilyl)ethyl>sulfonyl>amino>propionyl>amino>-1-methylethyl>-5-methyloxazole-4-carboxylic acid methylamide

(4'S)-5,4'-Dimethyl-2'-phenethyl-4',5'-dihydro-2,4'-bioxazoyl-4-carboxylic acid methylamide