(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

Base Information

• Chemical Name: (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane
• CAS No.: 128018-44-0
• Molecular Formula: C18H19NO3
• Molecular Weight: 297.354
• European Community (EC) Number: 603-250-4
• DSSTox Substance ID: DTXSID301172108
• Nikkaji Number: J853.897B
• ChEMBL ID: CHEMBL298965
• Mol file: 128018-44-0.mol

Synonyms:128018-44-0;(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane;CHEMBL298965;BENZYL N-[(1S)-1-[(2S)-OXIRAN-2-YL]-2-PHENYLETHYL]CARBAMATE;Carbamic acid, N-[(1S)-1-[(2S)-2-oxiranyl]-2-phenylethyl]-, phenylmethyl ester;3(S)-(N-(benzyloxycarbonyl)amino]-1,2(S)-epoxy-4-phenylbutane;3(S)-[N-(benzyloxycarbonyl)amino]-1,2(S)-epoxy-4-phenylbutane;SCHEMBL2575768;erythro-Cbz-phenylalanine epoxide;DTXSID301172108;BCP25736;BDBM50284944;N-Cbz-3-(S)-amino-1,2-(S)-epoxy-4-phenylbutane;3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-phenylbutane;benzyl (1S)-1-[(2S)-oxiranyl]-2-phenylethylcarbamate;benzyl (S)-1-((S)-oxiran-2-yl)-2-phenylethyl-carbamate;N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane;N-benzyloxycarbonyl 3 (S)-amino-1,2-(S)-epoxy-4-phenylbutane;N-benzyloxycarbonyl 3(S)-amino-1,2-(S)-epoxy-4-phenylbutane;N-benzyloxycarbonyl-3 (S)-amino-1,2(S)-epoxy-4-phenylbutane;N-benzyloxycarbonyl-3(S)-amino-1,2 (S) -epoxy-4-phenylbutane;N-benzyloxycarbonyl-3(S)-amino-1,2(S)-epoxy-4- phenylbutane;N-benzyloxycarbonyl-3(S)-amino-1,2(S)-epoxy-4-phenylbutane;((S)-1-(S)-Oxiranyl-2-phenyl-ethyl)-carbamic acid benzyl ester;3(S)-[N-(benzyloxycarbonyl) amino]-1,2(S)-epoxy-4-phenylbutane;3(S)-[N-(benzyloxycarbonyl)amino] -1,2(S) -epoxy-4-phenylbutane;3(S)-[N-(benzyloxycarbonyl)amino]-1,2(S) -epoxy-4-phenylbutane;N-benzyloxycarbonyl-3 (S) -amino-1, 2 (S) -epoxy-4-phenylbutane;N-benzyloxycarbonyl-3 (S) -amino-1,2(s) -epoxy-4-phenylbutane;Phenylmethyl N-[(1S)-1-[(2S)-2-oxiranyl]-2-phenylethyl]carbamate

Chemical Property of (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

Chemical Property:

• Melting Point: 77-80 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• Refractive Index: 1.593
• Boiling Point: 481.8 °C at 760 mmHg
• PKA: 11.98±0.46(Predicted)
• Flash Point: 245.2 °C
• PSA: 50.86000
• Density: 1.206 g/cm³
• LogP: 3.31380
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 297.13649347
• Heavy Atom Count: 22
• Complexity: 348

Purity/Quality:

99% ^*data from raw suppliers

(2S,3S)-1,2-EPOXY-3-(CBZ-AMINO)-4-PHENYLBUTANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)C(CC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3
• Isomeric SMILES: C1[C@@H](O1)[C@H](CC2=CC=CC=C2)NC(=O)OCC3=CC=CC=C3

Technology Process of (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

There total 20 articles about (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane 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: 99.0%

N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol (128018-43-9) → N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane (128018-44-0)

Guidance literature:

With potassium hydroxide; In ethanol; at 20 ℃; for 1h;

DOI:10.1021/jo052121t

Reference yield: 69.0%

(2S,3S)-3-(benzyloxycarbonylamino)-4-phenylbutane-1,2-diol (164394-36-9) → N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane (128018-44-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In chloroform; Heating;

DOI:10.1016/S0040-4039(99)01953-X

Reference yield: 45.0%

(3S)-3-(N-benzyloxycarbonylamino)-3-benzyl-2-oxo-1-bromopropane (19317-12-5,19317-09-0) → N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane (128018-44-0)

Guidance literature:

With sodium tetrahydroborate;

DOI:10.1016/0957-4166(95)00299-5

upstream raw materials:

N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol

(S)-2-(phenylmethoxycarbonyl)amino-1-phenylbut-3-ene

(3S)-3-(N-benzyloxycarbonylamino)-3-benzyl-2-oxo-1-bromopropane

(2S,3S)-3-(benzyloxycarbonylamino)-4-phenylbutane-1,2-diol

Downstream raw materials:

N-<1-phenyl-2(S)-<(benzyloxycarbonyl)amino>-3(R)-hydroxybutan>-4-L-prolyl-tert-butyl amide

((S)-1-(S)-Aziridin-2-yl-2-phenyl-ethyl)-carbamic acid benzyl ester

N-[3(S)-benzyloxycarbonylamino-2(R)-hydroxy-4-phenylbutyl]isoamylamine

3-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-4(R)-thiazolidinecarboxamide

Refernces

• 1、 Yin, Jingjun,Huffman, Mark A.,Conrad, Karen M.,Armstrong III, Joseph D.. "Highly diastereoselective catalytic Meerwein-Ponndorf-Verley reductions". . p. 840 - 843. Retrieved 2007/10/03.
• 2、 Honda, Yutaka,Katayama, Satoshi,Kojima, Mitsuhiko,Suzuki, Takayuki,Kishibata, Naomi,Izawa, Kunisuke. "New approaches to the industrial synthesis of HIV protease inhibitors". . p. 2061 - 2070. Retrieved 2007/10/03.