(2S)-4-amino-2-<<(4-methylphenyl)sulfonyl>amino>butan-1-ol

Base Information

• Chemical Name: (2S)-4-amino-2-<<(4-methylphenyl)sulfonyl>amino>butan-1-ol
• CAS No.: 124921-81-9
• Molecular Formula: C₁₁H₁₈N₂O₃S
• Molecular Weight: 258.342
• Mol file: 124921-81-9.mol

Synonyms:(2S)-4-amino-2-<<(4-methylphenyl)sulfonyl>amino>butan-1-ol

Chemical Property of (2S)-4-amino-2-<<(4-methylphenyl)sulfonyl>amino>butan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-4-amino-2-<<(4-methylphenyl)sulfonyl>amino>butan-1-ol

There total 2 articles about (2S)-4-amino-2-<<(4-methylphenyl)sulfonyl>amino>butan-1-ol 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: 86.0%

N2-(toluene-4-sulfonyl)-L-asparagine (36212-66-5) → (2S)-4-amino-2-<<(4-methylphenyl)sulfonyl>amino>butan-1-ol (124921-81-9)

Guidance literature:

With lithium borohydride; chloro-trimethyl-silane; In tetrahydrofuran; <10 deg C, 30 min, then RT, 1h, then reflux, 2h;

DOI:10.1021/jo00299a013

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (2S)-4-amino-2-<<(4-methylphenyl)sulfonyl>amino>butan-1-ol (124921-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / 1N aq. NaOH / acetone / 40 - 50 °C / pH 9-10

2: 86 percent / LiBH₄, (CH₃)3SiCl / tetrahydrofuran / <10 deg C, 30 min, then RT, 1h, then reflux, 2h

With sodium hydroxide; lithium borohydride; chloro-trimethyl-silane; In tetrahydrofuran; acetone;

DOI:10.1021/jo00299a013

Reference yield:

(2S)-4-amino-2-<<(4-methylphenyl)sulfonyl>amino>butan-1-ol (124921-81-9) → (3'S,6S)-3-<4'-<(tert-butyldiphenylsilyl)oxy>-3'-<<(4-methylphenyl)sulfonyl>amino>butyl>-6-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-(methylthio)-3,4,5,6-tetrahydropyrimidine hydroperchlorate

Guidance literature:

Multi-step reaction with 3 steps

1: acetonitrile / 35 deg C, 3h, then standing overnight

2: imidazole / CH₂Cl₂ / 2 h / Ambient temperature

3: 1.) methyl trifluoromethanesulfonate, ethyldiisopropylamine, 2.) ethyldiisopropylamine / 1.) CH₂Cl₂, 0-10 deg C, 2h, 2.) reflux, overnight

With 1H-imidazole; N-ethyl-N,N-diisopropylamine; methyl trifluoromethanesulfonate; In dichloromethane; acetonitrile;

DOI:10.1021/jo00299a013

upstream raw materials:

N²-(toluene-4-sulfonyl)-L-asparagine

p-toluenesulfonyl chloride

Downstream raw materials:

N-((S)-3-{3-[(S)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methylsulfanyl-propyl]-thioureido}-1-hydroxymethyl-propyl)-4-methyl-benzenesulfonamide

<(S)-4-Amino-2-<(4-methylphenyl)sulfonylamino>butyl>ether

(2S,8S)-2-<<(tert-butyldimethylsilyl)oxy>methyl>-8-<<(tert-butyldiphenylsilyl)oxy>methyl>-1-<(4-methylphenyl)sulfonyl>-1,5,9-triazabicyclo<4.4.0>dec-9-ene

N-<(3S)-4-<(tert-butyldimethylsilyl)oxy>-3-<<(4-methylphenyl)sulfonyl>amino>butyl>-N'-<(2S)-1-<(tert-butyldiphenylsilyl)oxy>-5-thiahex-2-yl>thiourea