Z-SER(TOS)-OME

Base Information

• Chemical Name: Z-SER(TOS)-OME
• CAS No.: 1492-52-0
• Molecular Formula: C19H21 N O7 S
• Molecular Weight: 407.444
• Mol file: 1492-52-0.mol

Synonyms:L-Serine,N-[(phenylmethoxy)carbonyl]-, methyl ester, 4-methylbenzenesulfonate (ester)(9CI); Serine, N-carboxy-, N-benzyl methyl ester, p-toluenesulfonate (7CI);Serine, N-carboxy-, N-benzyl methyl ester, p-toluenesulfonate (ester), L-(8CI); Methyl(S)-2-[(benzyloxycarbonyl)amino]-3-(p-toluenesulfonyloxy)propanoate

Chemical Property of Z-SER(TOS)-OME

Chemical Property:

• Vapor Pressure: 7.23E-14mmHg at 25°C
• Boiling Point: 589.3°C at 760 mmHg
• Flash Point: 310.2°C
• PSA: 116.38000
• Density: 1.3g/cm³
• LogP: 3.64000
• Storage Temp.: -15°C

Purity/Quality:

95% ^*data from raw suppliers

Z-O-4-toluenesulfonyl-L-serine methyl ester 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Z-SER(TOS)-OME

There total 3 articles about Z-SER(TOS)-OME 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:

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) + p-toluenesulfonyl chloride (98-59-9) → methyl (S)-2-(benzyloxycarbonlamino)-3-(p-toluenesulfonyl)propionate (1492-52-0)

Guidance literature:

With pyridine;

DOI:10.1021/ja00891a019

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → methyl (S)-2-(benzyloxycarbonlamino)-3-(p-toluenesulfonyl)propionate (1492-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / SOCl₂

2: pyridine

With thionyl chloride; In pyridine;

DOI:10.1016/S0040-4039(03)01222-X

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → methyl (S)-2-(benzyloxycarbonlamino)-3-(p-toluenesulfonyl)propionate (1492-52-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / NaHCO₃ / toluene; H₂O

2: 99 percent / SOCl₂

3: pyridine

With thionyl chloride; sodium hydrogencarbonate; In pyridine; water; toluene;

DOI:10.1016/S0040-4039(03)01222-X

upstream raw materials:

N-benzyloxycarbonyl-L-serine methyl ester

p-toluenesulfonyl chloride

N-(benzyloxycarbonyl)-L-serine

benzyl chloroformate

Downstream raw materials:

methyl (R)-(+)-2-(benzyloxycarbonylamino)-3-chloropropionoate

methyl 2-(R)-(benzyloxycarbonylamino)-3-bromomethylpropionate

methyl N-((benzyloxy)carbonyl)-3-iodo-L-alaninate

4-benzyloxycarbonylamino-2-methylpyrazolidin-3-one

Refernces

• 1、 Olsen,Severinsen,Rasmussen,Hentzer,Givskov,Nielsen. "Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers". . p. 325 - 328. Retrieved 2007/10/03.