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

Base Information

• Chemical Name: methyl (2R,3R)-N-(p-toluenesulfonyl)-2-amino-3,4-dihydroxybutyrate
• CAS No.: 934490-08-1
• Molecular Formula: C₁₂H₁₇NO₆S
• Molecular Weight: 303.336
• Mol file: 934490-08-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about methyl (2R,3R)-N-(p-toluenesulfonyl)-2-amino-3,4-dihydroxybutyrate 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: 80.0%

dimethyl (2R,3R)-N-(p-toluenesulfonyl)-3-amino-2-hydroxysuccinate (176435-38-4) → methyl (2R,3R)-N-(p-toluenesulfonyl)-2-amino-3,4-dihydroxybutyrate (934490-08-1)

Guidance literature:

dimethyl (2R,3R)-N-(p-toluenesulfonyl)-3-amino-2-hydroxysuccinate; With dimethylsulfide borane complex; In tetrahydrofuran; for 0.666667h;

With sodium tetrahydroborate; In tetrahydrofuran;

DOI:10.1002/adsc.200505252

Reference yield: 70.0%

methyl (2R,3R)-N-(p-toluenesulfonyl)-2-amino-3,4-dihydroxybutyrate (934490-08-1) + p-toluenesulfonyl chloride (98-59-9) → methyl (2R,3R)-3-hydroxy-2-(4-methylphenylsulfonamido)-4-tosyloxybutanoate (934490-09-2)

Guidance literature:

With di(n-butyl)tin oxide; triethylamine; In dichloromethane;

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

upstream raw materials:

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

Downstream raw materials:

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

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