(2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane

Base Information

• Chemical Name: (2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane
• CAS No.: 128018-43-9
• Molecular Formula: C18H20ClNO3
• Molecular Weight: 333.815
• DSSTox Substance ID: DTXSID90446231
• Wikidata: Q82264833
• Mol file: 128018-43-9.mol

Synonyms:128018-43-9;(2S,3S)-3-(BENZYLOXYCARBONYLAMINO)-1-CHLORO-2-HYDROXY-4-PHENYLBUTANE;Benzyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate;benzyl N-[(2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamate;Benzyl [(2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamate;SCHEMBL2577615;DTXSID90446231;A2675;N-CBZ-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol;N-Cbz-3-(S)-amino-1-chloro-4-phenyl-2(S)-butanol;3(S)-(benzyloxyformamido)-1-chloro-4-phenyl-2(S)-butanol;N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol;N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)butanol;N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl2(S)-butanol;n-benzyloxycarbonyl-3(s)-amino-l-chloro-4-phenyl-2(s)-butanol;N-benzyloxycarbonyl-3(S)-amino1-chloro4-phenyl-2(S)-butanol;Benzyl((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate;N-benzyloxycarbonyl-3 (S)-amino-1-chloro-4 -phenyl-2(S)butanol;N-benzyloxycarbonyl-3 (S)-amino-1-chloro-4-phenyl-2 (S)-butanol;N-benzyloxycarbonyl-3 (S)-amino-1-chloro-4-phenyl-2(S)-butanol;N-benzyloxycarbonyl-3(S )-amino-1-chloro-4-phenyl-2-(S)-butanol;N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2 (S) -butanol;N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2-(S)-butanol

Chemical Property of (2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.583
• Boiling Point: 535.079 °C at 760 mmHg
• Flash Point: 277.406 °C
• PSA: 62.05000
• Density: 1.232g/cm³
• LogP: 3.32820
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 333.1131712
• Heavy Atom Count: 23
• Complexity: 341

Purity/Quality:

99% ^*data from raw suppliers

Benzyl((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(CCl)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H]([C@@H](CCl)O)NC(=O)OCC2=CC=CC=C2

Technology Process of (2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane

There total 15 articles about (2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-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: 94.0%

(S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate (26049-94-5) → N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol (128018-43-9) + (2R,3S)-1-chloro-2-hydroxy-3-N-benzyloxycarbonylamino-4-phenylbutane (183255-96-1)

Guidance literature:

With aluminum isopropoxide; isopropyl alcohol; In toluene; at 50 ℃; for 18h;

DOI:10.1021/jo052121t

Reference yield: 92.0%

(S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate (26049-94-5) → N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol (128018-43-9)

Guidance literature:

With C₃₈H₄₀ClN₂O₃RhS; In dichloromethane; at 25 ℃; for 1h; diastereoselective reaction; Schlenk technique;

DOI:10.1039/c9cc09793g

Reference yield: 43.0%

→ (S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate (26049-94-5) + N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol (128018-43-9)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol;

DOI:10.1021/jm00054a014

upstream raw materials:

(S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate

N-carbobenzoxy-L-phenylalanine methyl ester

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

benzyl chloroformate

Downstream raw materials:

N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane

1-((2R,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-3-ethyl-1-isobutyl-urea

1-((2R,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-1-isobutyl-3-isopropyl-urea

1-((2R,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-1-isobutyl-3-propyl-urea

Refernces

• 1、 Chen, Gen-Qiang,Lang, Qi-Wei,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie,Wang, Fangyuan,Wu, Ting,Yin, Congcong,Zhang, Xumu,Zheng, Long-Sheng. "Rh(iii)-Catalyzed diastereoselective transfer hydrogenation: An efficient entry to key intermediates of HIV protease inhibitors". supporting information. p. 3119 - 3122. Retrieved 2020/03/23.
• 2、 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.