Z-Asp(otbu)-otbu

Base Information

• Chemical Name: Z-Asp(otbu)-otbu
• CAS No.: 42417-76-5
• Molecular Formula: C20H29NO6
• Molecular Weight: 379.453
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID801163700
• Nikkaji Number: J1.346.502I
• Mol file: 42417-76-5.mol

Synonyms:42417-76-5;Z-ASP(OTBU)-OTBU;Z-L-aspartic acid-di-tert-butyl ester;ditert-butyl (2S)-2-(phenylmethoxycarbonylamino)butanedioate;(S)-Di-tert-butyl 2-(((benzyloxy)carbonyl)amino)succinate;Z-L-aspartic acid di-tert.butyl ester;DTXSID801163700;MFCD00270579;AM81627;Z-L-Aspartic acid-alpha,beta-di-t-butyl ester;(S)-di-tert-butyl 2-(benzyloxycarbonylamino)succinate;(S)-Di-tert-butyl2-(((benzyloxy)carbonyl)amino)succinate;1,4-Bis(1,1-dimethylethyl) N-[(phenylmethoxy)carbonyl]-L-aspartate

Chemical Property of Z-Asp(otbu)-otbu

Chemical Property:

• Boiling Point: 485.5±45.0 °C(Predicted)
• PKA: 10.43±0.46(Predicted)
• PSA: 90.93000
• Density: 1.115±0.06 g/cm3(Predicted)
• LogP: 3.74580
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 379.19948764
• Heavy Atom Count: 27
• Complexity: 512

Purity/Quality:

99% ^*data from raw suppliers

Z-L-aspartic acid-di-tert-butyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(C(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)C[C@@H](C(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1

Technology Process of Z-Asp(otbu)-otbu

There total 9 articles about Z-Asp(otbu)-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: 87.0%

acetic acid tert-butyl ester (540-88-5) + N-Cbz-L-Asp (1152-61-0) → 1,4-di-tert-butyl (2S)-2-{[(benzyloxy)carbonyl]amino}butanedioate (42417-76-5)

Guidance literature:

With boron trifluoride diethyl etherate; at 20 ℃; for 48h;

DOI:10.1021/jacs.6b01327

Reference yield:

acetic acid tert-butyl ester (540-88-5) + N-Cbz-L-Asp (1152-61-0) → (S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester (47307-26-6,149967-07-7) + Z-D(tBu)-OH (5545-52-8) + 1,4-di-tert-butyl (2S)-2-{[(benzyloxy)carbonyl]amino}butanedioate (42417-76-5)

Guidance literature:

sulfuric acid; at 20 ℃; for 5.5h; Product distribution / selectivity;

Reference yield:

tert-butyl formate (762-75-4) + N-Cbz-L-Asp (1152-61-0) → (S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester (47307-26-6,149967-07-7) + Z-D(tBu)-OH (5545-52-8) + 1,4-di-tert-butyl (2S)-2-{[(benzyloxy)carbonyl]amino}butanedioate (42417-76-5)

Guidance literature:

boron trifluoride diethyl etherate; at 20 ℃; for 5h; Product distribution / selectivity;

upstream raw materials:

tert-butyl formate

N-Cbz-L-Asp

bromoacetic acid tert-butyl ester

tert-butyl methyl ether

Downstream raw materials:

(S)-di-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)acetamido)succinate

Refernces

• 1、 Dong, Shuai,Indukuri, Kiran,Clive, Derrick L. J.,Gao, Jin-Ming. "Synthesis of models of the BC ring systems of MPC1001 and MPC1001F". supporting information. p. 8271 - 8274. Retrieved 2016/07/06.
• 2、 -. "Preparation of protected amino acids". Page column 4. . Retrieved 2008/06/13.