Z-SER(TBU)-OTBU

Base Information

• Chemical Name: Z-SER(TBU)-OTBU
• CAS No.: 58455-98-4
• Molecular Formula: C19H29NO5
• Molecular Weight: 351.443
• Mol file: 58455-98-4.mol

Synonyms:N-ALPHA-CARBOBENZOXY-O-T-BUTYL-L-SERINE T-BUTYL ESTER;Z-T-BUTYL-L-SERINE T-BUTYL ESTER;Z-O-T-BUTYL-L-SERINE T-BUTYL ESTER;Z-SER(TBU)-OTBU;Z-T-BUTYL-L-SERINE T-BUTYLESTER LIQUID

Chemical Property of Z-SER(TBU)-OTBU

Chemical Property:

• PSA: 73.86000
• LogP: 3.82910

Purity/Quality:

97% ^*data from raw suppliers

Z-SER(TBU)-OTBU 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Z-SER(TBU)-OTBU

There total 5 articles about Z-SER(TBU)-OTBU 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: 80.0%

N-(benzyloxycarbonyl)-L-serine (1145-80-8) + isobutene (115-11-7,15220-85-6) → O-(1,1-dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-serine 1,1-dimethylethyl ester (58455-98-4)

Guidance literature:

With sulfuric acid; In dichloromethane; at -25 - 20 ℃;

DOI:10.1016/S0040-4020(00)00280-5

Reference yield: 60.0%

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + N-(benzyloxycarbonyl)-L-serine (1145-80-8) → O-(1,1-dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-serine 1,1-dimethylethyl ester (58455-98-4) + 2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester (59859-77-7)

Guidance literature:

In tetrahydrofuran; dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(97)10851-6

Reference yield:

(S)-3-acetoxy-2-(benzyloxycarbonylamino)propanoic acid (19645-29-5) → O-(1,1-dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-serine 1,1-dimethylethyl ester (58455-98-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / 96 percent H₂SO₄ / CH₂Cl₂ / -25 - 20 °C

2: 91 percent / N₂H₂*H₂O / ethanol / 0 - 20 °C

3: 89 percent / 100 percent HNO₃ / CH₂Cl₂ / 2 h / 0 °C

4: 80 percent / 96 percent H₂SO₄ / CH₂Cl₂ / -25 - 20 °C

With sulfuric acid; diazene; nitric acid; In ethanol; dichloromethane; 1: Alkylation / 2: hydrazinolysis / 3: nitrolysis / 4: Alkylation;

DOI:10.1016/S0040-4020(00)00280-5

upstream raw materials:

N-(benzyloxycarbonyl)-L-serine

isobutene

tert-Butyl 2,2,2-trichloroacetimidate

(S)-3-acetoxy-2-(benzyloxycarbonylamino)propanoic acid

Downstream raw materials:

2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester

Z-Ser(Bu^t)-Gly-Gly-Ser(Bu^t)-OBu^t

Z-Gyl-Gly-Ser(Bu^t)-OBu^t

Z-Gly-Ser(Bu^t)-OBu^t

Refernces

• 1、 Thierry, Josiane,Yue, Chongwei,Potier, Pierre. "2-Phenyl isopropyl and t-butyl trichloroacetimidates: Useful reagents for ester preparation of N-protected amino acids under neutral conditions". . p. 1557 - 1560. Retrieved 2007/10/03.
• 2、 Uchiyama,Yoshino,Takemoto,Achiwa. "Synthesis of the 2',3'-dideoxynucleoside derivatives of the specific binding peptide part of CD4". . p. 3091 - 3093. Retrieved 2007/10/02.