methyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-3-hydroxy-2-O-[(4-nitrophenyl)sulfonyl]pentanoate

Base Information

• Chemical Name: methyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-3-hydroxy-2-O-[(4-nitrophenyl)sulfonyl]pentanoate
• CAS No.: 848829-56-1
• Molecular Formula: C₁₇H₂₄N₂O₁₀S
• Molecular Weight: 448.451
• Mol file: 848829-56-1.mol

Synonyms:methyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-3-hydroxy-2-O-[(4-nitrophenyl)sulfonyl]pentanoate

Chemical Property of methyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-3-hydroxy-2-O-[(4-nitrophenyl)sulfonyl]pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-3-hydroxy-2-O-[(4-nitrophenyl)sulfonyl]pentanoate

There total 3 articles about methyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-3-hydroxy-2-O-[(4-nitrophenyl)sulfonyl]pentanoate 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: 65.0%

methyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-2,3-dihydroxypentanoate (848830-05-7) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → methyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-3-hydroxy-2-O-[(4-nitrophenyl)sulfonyl]pentanoate (848829-56-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1002/anie.200461823

Reference yield:

N-(tert-butoxycarbonyl)-3-aminopropanal (58885-60-2) → methyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-3-hydroxy-2-O-[(4-nitrophenyl)sulfonyl]pentanoate (848829-56-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / CH₂Cl₂ / 20 h / 0 - 20 °C

2: AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

3: NEt₃ / CH₂Cl₂ / 16 h / 4 °C

With AD-mix-α; methanesulfonamide; triethylamine; In dichloromethane; water; tert-butyl alcohol; 1: Wittig reaction / 2: Sharpless asymmetric dihydroxylation;

DOI:10.1002/chem.200501274

Reference yield:

methyl (E)-5-<(t-butyloxycarbonyl)amino>pent-2-enoate (102845-66-9) → methyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-3-hydroxy-2-O-[(4-nitrophenyl)sulfonyl]pentanoate (848829-56-1)

Guidance literature:

Multi-step reaction with 2 steps

1: AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

2: NEt₃ / CH₂Cl₂ / 16 h / 4 °C

With AD-mix-α; methanesulfonamide; triethylamine; In dichloromethane; water; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation;

DOI:10.1002/chem.200501274

upstream raw materials:

methyl (2R,3S)-5-[(tert-butoxycarbonyl)amino]-2,3-dihydroxypentanoate

4-Nitrobenzenesulfonyl chloride

N-(tert-butoxycarbonyl)-3-aminopropanal

methyl (E)-5-<(t-butyloxycarbonyl)amino>pent-2-enoate