2-{[(Benzyloxy)(hydroxy)methylidene]amino}-3-(phenylsulfanyl)propanoate

Base Information

• Chemical Name: 2-{[(Benzyloxy)(hydroxy)methylidene]amino}-3-(phenylsulfanyl)propanoate
• CAS No.: 159453-24-4
• Molecular Formula: C₁₇H₁₇NO₄S
• Molecular Weight: 331.392
• DSSTox Substance ID: DTXSID10936104
• Wikidata: Q72516363
• Mol file: 159453-24-4.mol

Synonyms:DTXSID10936104;2-{[(Benzyloxy)(hydroxy)methylidene]amino}-3-(phenylsulfanyl)propanoate

Chemical Property of 2-{[(Benzyloxy)(hydroxy)methylidene]amino}-3-(phenylsulfanyl)propanoate

Chemical Property:

• Appearance/Colour: light yellow crystal powder
• Vapor Pressure: 8.07E-13mmHg at 25°C
• Melting Point: 94-97 °C
• Refractive Index: -55 ° (C=2, EtOH)
• Boiling Point: 547.5 °C at 760 mmHg
• PKA: 3.48±0.10(Predicted)
• Flash Point: 284.9 °C
• PSA: 100.93000
• Density: 1.31 g/cm³
• LogP: 3.54920
• Solubility.: soluble in Methanol
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 330.08000417
• Heavy Atom Count: 23
• Complexity: 373

Purity/Quality:

99% ^*data from raw suppliers

N-Carbobenzyloxy-3-phenylthio-L-alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CSC2=CC=CC=C2)C(=O)[O-]
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CSC2=CC=CC=C2)C(=O)[O-]
• Uses: N-Carbobenzyloxy-3-phenylthio-L-alanine (cas# 159453-24-4) is a compound useful in organic synthesis.

Technology Process of 2-{[(Benzyloxy)(hydroxy)methylidene]amino}-3-(phenylsulfanyl)propanoate

There total 21 articles about 2-{[(Benzyloxy)(hydroxy)methylidene]amino}-3-(phenylsulfanyl)propanoate 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: 98.0%

N-benzyloxycarbonyl-S-phenyl-L-cysteine methyl ester (153277-33-9) → N-benzyloxycarbonyl-S-phenyl-L-cysteine (82611-65-2,159453-24-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 2h;

DOI:10.1016/0040-4039(93)88117-2

Reference yield: 96.6%

bromobenzene (108-86-1,52753-63-6) + N,N'-bis-benzyloxycarbonylcystine (6968-11-2,102203-30-5,102339-44-6) → N-benzyloxycarbonyl S-benzylcysteine (5619-12-5,95585-39-0) + N-benzyloxycarbonyl-S-phenyl-L-cysteine (82611-65-2,159453-24-4)

Guidance literature:

With copper; In N,N-dimethyl-formamide; at 120 ℃; for 19h;

Reference yield: 84.0%

L-carbobenzyloxy-β-chloroalanine (7625-65-2) + thiophenol (108-98-5) → N-benzyloxycarbonyl-S-phenyl-L-cysteine (82611-65-2,159453-24-4)

Guidance literature:

L-carbobenzyloxy-β-chloroalanine; thiophenol; With sodium hydrogencarbonate; In water; at 20 - 60 ℃; for 2h;

With hydrogenchloride; In water;

upstream raw materials:

S-phenyl-L-cysteine

benzyl chloroformate

N-benzyloxycarbonyl-S-phenyl-L-cysteine methyl ester

benzoic acid benzyl ester

Downstream raw materials:

benzyl [(2R,3R)-4-chloro-3-hydroxy-1-(phenylsulfanyl)-2-butanyl]carbamate

benzyl [(1R)-1-[(2S)-2-oxiranyl]-2-(phenylsulfanyl)ethyl]carbamate

benzyl [(2R,3S)-4-chloro-3-hydroxy-1-(phenylsulfanyl)-2-butanyl]carbamate

Refernces

• 1、 -. "Method of making HIV protease inhibitors". . . Retrieved 2008/06/13.
• 2、 -. "Process for S-Aryl cysteine". Example 6. . Retrieved 2008/06/13.