methyl (2R,3S)-N-(p-toluenesulfonyl)-2-amino-3-hydroxy-4-azidobutyrate

Base Information

• Chemical Name: methyl (2R,3S)-N-(p-toluenesulfonyl)-2-amino-3-hydroxy-4-azidobutyrate
• CAS No.: 934490-10-5
• Molecular Formula: C₁₂H₁₆N₄O₅S
• Molecular Weight: 328.349
• Mol file: 934490-10-5.mol

Synonyms:methyl (2R,3S)-N-(p-toluenesulfonyl)-2-amino-3-hydroxy-4-azidobutyrate

Chemical Property of methyl (2R,3S)-N-(p-toluenesulfonyl)-2-amino-3-hydroxy-4-azidobutyrate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3S)-N-(p-toluenesulfonyl)-2-amino-3-hydroxy-4-azidobutyrate

There total 3 articles about methyl (2R,3S)-N-(p-toluenesulfonyl)-2-amino-3-hydroxy-4-azidobutyrate 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: 63.0%

methyl (2R,3R)-3-hydroxy-2-(4-methylphenylsulfonamido)-4-tosyloxybutanoate (934490-09-2) → methyl (2R,3S)-N-(p-toluenesulfonyl)-2-amino-3-hydroxy-4-azidobutyrate (934490-10-5)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 60 ℃; for 4h;

DOI:10.1002/adsc.200505252

Reference yield:

methyl (2R,3R)-N-(p-toluenesulfonyl)-2-amino-3,4-dihydroxybutyrate (934490-08-1) → methyl (2R,3S)-N-(p-toluenesulfonyl)-2-amino-3-hydroxy-4-azidobutyrate (934490-10-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / Bu₂SnO; Et₃N / CH₂Cl₂

2: 63 percent / NaN₃ / dimethylsulfoxide / 4 h / 60 °C

With sodium azide; di(n-butyl)tin oxide; triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1002/adsc.200505252

Reference yield:

dimethyl (2R,3R)-N-(p-toluenesulfonyl)-3-amino-2-hydroxysuccinate (176435-38-4) → methyl (2R,3S)-N-(p-toluenesulfonyl)-2-amino-3-hydroxy-4-azidobutyrate (934490-10-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BH₃*SMe₂ / tetrahydrofuran / 0.67 h

1.2: 80 percent / NaBH₄ / tetrahydrofuran

2.1: 70 percent / Bu₂SnO; Et₃N / CH₂Cl₂

3.1: 63 percent / NaN₃ / dimethylsulfoxide / 4 h / 60 °C

With sodium azide; dimethylsulfide borane complex; di(n-butyl)tin oxide; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1002/adsc.200505252

upstream raw materials:

methyl (2R,3R)-3-hydroxy-2-(4-methylphenylsulfonamido)-4-tosyloxybutanoate

methyl (2R,3R)-N-(p-toluenesulfonyl)-2-amino-3,4-dihydroxybutyrate

dimethyl (2R,3R)-N-(p-toluenesulfonyl)-3-amino-2-hydroxysuccinate