N-(t-Boc)-3-phenyl Isoserine Ethyl Ester

Base Information

• Chemical Name: N-(t-Boc)-3-phenyl Isoserine Ethyl Ester
• CAS No.: 143527-75-7
• Molecular Formula: C16H23NO5
• Molecular Weight: 309.362
• DSSTox Substance ID: DTXSID30448577
• Wikidata: Q82267636
• Mol file: 143527-75-7.mol

Synonyms:N-(t-Boc)-3-phenyl Isoserine Ethyl Ester;143527-75-7;ethyl (2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate;DTXSID30448577;XOGCYMFNVKHELE-QWHCGFSZSA-N;AKOS030241519;CS-0347731;EN300-7548200;J-007829;(2r,3s)-ethyl 3-(t-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate;Ethyl (2r,3s)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoate;ethyl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate;ethyl (2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoate

Chemical Property of N-(t-Boc)-3-phenyl Isoserine Ethyl Ester

Chemical Property:

• PSA: 88.35000
• LogP: 2.38080
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate, Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 309.15762283
• Heavy Atom Count: 22
• Complexity: 371

Purity/Quality:

97% ^*data from raw suppliers

N-(t-Boc)-3-phenylIsoserineEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C(C1=CC=CC=C1)NC(=O)OC(C)(C)C)O
• Isomeric SMILES: CCOC(=O)[C@@H]([C@H](C1=CC=CC=C1)NC(=O)OC(C)(C)C)O
• Uses: N-(t-Boc)-3-phenyl Isoserine Ethyl Ester (cas# 143527-75-7) is a compound useful in organic synthesis.

Technology Process of N-(t-Boc)-3-phenyl Isoserine Ethyl Ester

There total 9 articles about N-(t-Boc)-3-phenyl Isoserine Ethyl Ester 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: 76.0%

di-tert-butyl dicarbonate (24424-99-5) + (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester (143615-00-3) → (2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine (143527-75-7)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(00)79128-3

Reference yield: 68.0%

di-tert-butyl dicarbonate (24424-99-5) + (2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester (144787-20-2) → (2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine (143527-75-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 69h;

DOI:10.1016/0957-4166(95)00295-Z

Reference yield:

(2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester (144787-20-2) → (2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine (143527-75-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / H₂ / 10percent Pd/C / ethyl acetate / 760 Torr

2: 76 percent / NaHCO₃ / CH₂Cl₂ / 20 °C

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(00)79128-3

upstream raw materials:

di-tert-butyl dicarbonate

(2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester

(2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester

benzaldehyde

Downstream raw materials:

ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate

10-deacetyl-7,10-diTroc-baccatin III

Docetaxel

taxol