N-Boc-L-homoserine Methyl Ester 4-Methylbenzenesulfonate

Base Information

• Chemical Name: N-Boc-L-homoserine Methyl Ester 4-Methylbenzenesulfonate
• CAS No.: 120042-09-3
• Molecular Formula: C17H25 N O7 S
• Molecular Weight: 387.454
• Mol file: 120042-09-3.mol

Synonyms:L-Homoserine,N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester, 4-methylbenzenesulfonate(ester) (9CI)

Chemical Property of N-Boc-L-homoserine Methyl Ester 4-Methylbenzenesulfonate

Chemical Property:

• Boiling Point: 532.7±50.0 °C(Predicted)
• PKA: 10.83±0.46(Predicted)
• PSA: 116.38000
• Density: 1.216±0.06 g/cm3(Predicted)
• LogP: 3.62840
• Solubility.: Chloroform, Methanol

Purity/Quality:

97% ^*data from raw suppliers

(S)-N-Boc-L-homoserineMethylEsterTosylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc-L-homoserine Methyl Ester 4-Methylbenzenesulfonate is used in the synthesis of the functionalizable methionine surrogate azidohomoalanine using Boc-homoserine as precursor.

Technology Process of N-Boc-L-homoserine Methyl Ester 4-Methylbenzenesulfonate

There total 3 articles about N-Boc-L-homoserine Methyl Ester 4-Methylbenzenesulfonate 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:

p-toluenesulfonyl chloride (98-59-9) + methyl (S)-4-hydroxy-2-((tert-butoxy)carbonylamino)-butyrate (120042-11-7,258351-86-9) → methyl N-(tert-butoxycarbonyl)-O-tosyl-L-homoserinate (120042-09-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → methyl N-(tert-butoxycarbonyl)-O-tosyl-L-homoserinate (120042-09-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / water; 1,4-dioxane / 24 h / 0 - 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C

3: pyridine / 8 h / 0 °C

With pyridine; potassium carbonate; sodium hydroxide; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1002/cmdc.202100451

Reference yield:

L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid (41088-86-2) → methyl N-(tert-butoxycarbonyl)-O-tosyl-L-homoserinate (120042-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C

2: pyridine / 8 h / 0 °C

With pyridine; potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1002/cmdc.202100451

upstream raw materials:

p-toluenesulfonyl chloride

methyl (S)-4-hydroxy-2-((tert-butoxy)carbonylamino)-butyrate

di-tert-butyl dicarbonate

L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid

Downstream raw materials:

N-(tert-butyldimethylsilyloxycarbonyl)-O-(p-tolylsulfonyl)-L-homoserine methyl ester