tert-Butyl tosyl-DL-alaninate

Base Information

• Chemical Name: tert-Butyl tosyl-DL-alaninate
• CAS No.: 69320-91-8
• Molecular Formula: C₁₄H₂₁NO₄S
• Molecular Weight: 299.391
• DSSTox Substance ID: DTXSID501189913
• Nikkaji Number: J899.349A
• Mol file: 69320-91-8.mol

Synonyms:tert-Butyl tosyl-DL-alaninate;69320-91-8;DTXSID501189913;N-[(4-Methylphenyl)sulfonyl]alanine 1,1-dimethylethyl ester

Chemical Property of tert-Butyl tosyl-DL-alaninate

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 299.11912932
• Heavy Atom Count: 20
• Complexity: 425

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(C)C(=O)OC(C)(C)C

Technology Process of tert-Butyl tosyl-DL-alaninate

There total 3 articles about tert-Butyl tosyl-DL-alaninate 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:

tert-butyl 2-(((benzyloxy)carbonyl)amino)propanoate (16881-40-6) + p-toluenesulfonyl chloride (98-59-9) → 2-(Toluene-4-sulfonylamino)-propionic acid tert-butyl ester (69320-91-8)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; Yield given. Multistep reaction; 1.) THF, 24 h, 2.) 0 deg C, 5 h;

DOI:10.1021/jo980205e

Reference yield:

N-(p-toluenesulfonyl)-DL-alanine (21957-58-4,85471-45-0,4816-81-3) + tert-butyl alcohol (75-65-0) → 2-(Toluene-4-sulfonylamino)-propionic acid tert-butyl ester (69320-91-8)

Guidance literature:

With sulfuric acid; In benzene; Heating;

Reference yield:

N-(p-toluenesulfonyl)-d,l-alanyl chloride (56271-34-2) + tert-butyl alcohol (75-65-0) → 2-(Toluene-4-sulfonylamino)-propionic acid tert-butyl ester (69320-91-8)

Guidance literature:

at 35 - 40 ℃;

upstream raw materials:

tert-butyl 2-(((benzyloxy)carbonyl)amino)propanoate

p-toluenesulfonyl chloride

N-(p-toluenesulfonyl)-DL-alanine

tert-butyl alcohol

Downstream raw materials:

(2R,3S)-3-Hydroxy-3-((4S,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester

(2S,3S)-3-Hydroxy-3-((4S,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester

(2R,3S)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester