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

Base Information

• Chemical Name: methyl (2R,3R)-3-hydroxy-2-(4-methylphenylsulfonamido)-4-tosyloxybutanoate
• CAS No.: 934490-09-2
• Molecular Formula: C₁₉H₂₃NO₈S₂
• Molecular Weight: 457.526
• Mol file: 934490-09-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about methyl (2R,3R)-3-hydroxy-2-(4-methylphenylsulfonamido)-4-tosyloxybutanoate 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: 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:

dimethyl (2R,3R)-N-(p-toluenesulfonyl)-3-amino-2-hydroxysuccinate (176435-38-4) → methyl (2R,3R)-3-hydroxy-2-(4-methylphenylsulfonamido)-4-tosyloxybutanoate (934490-09-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BH₃*SMe₂ / tetrahydrofuran / 0.67 h

1.2: 80 percent / NaBH₄ / tetrahydrofuran

2.1: 70 percent / Bu₂SnO; Et₃N / CH₂Cl₂

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

DOI:10.1002/adsc.200505252

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

upstream raw materials:

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

p-toluenesulfonyl chloride

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

Downstream raw materials:

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