benzyl N-[(1S)-1-[[1-benzyl-2-[[(1R)-1-[[(2S)-2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]-2-phenyl-ethyl]-ethoxy-phosphoryl]-2-hydroxy-ethyl]carbamoyl]-2-methyl-propyl]carbamate

Base Information

• Chemical Name: benzyl N-[(1S)-1-[[1-benzyl-2-[[(1R)-1-[[(2S)-2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]-2-phenyl-ethyl]-ethoxy-phosphoryl]-2-hydroxy-ethyl]carbamoyl]-2-methyl-propyl]carbamate
• CAS No.: 146063-29-8
• Molecular Formula: C45H57 N4 O9 P
• Molecular Weight: 828.9292
• DSSTox Substance ID: DTXSID40932755
• Mol file: 146063-29-8.mol

Synonyms:146063-29-8;DTXSID40932755;benzyl N-[(1S)-1-[[1-benzyl-2-[[(1R)-1-[[(2S)-2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]-2-phenyl-ethyl]-ethoxy-phosphoryl]-2-hydroxy-ethyl]carbamoyl]-2-methyl-propyl]carbamate;N-[8-Benzyl-10-ethoxy-3,6,9-trihydroxy-10-oxo-1,12-diphenyl-5-(propan-2-yl)-2-oxa-4,7-diaza-10lambda~5~-phosphadodeca-3,6-dien-11-yl]-2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-methylbutanimidic acid

Chemical Property of benzyl N-[(1S)-1-[[1-benzyl-2-[[(1R)-1-[[(2S)-2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]-2-phenyl-ethyl]-ethoxy-phosphoryl]-2-hydroxy-ethyl]carbamoyl]-2-methyl-propyl]carbamate

Chemical Property:

• PSA: 191.20000
• Density: 1.209g/cm³
• LogP: 8.49750
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 23
• Exact Mass: 828.38631641
• Heavy Atom Count: 59
• Complexity: 1330

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C(CC1=CC=CC=C1)NC(=O)C(C(C)C)NC(=O)OCC2=CC=CC=C2)C(C(CC3=CC=CC=C3)NC(=O)C(C(C)C)NC(=O)OCC4=CC=CC=C4)O
• Isomeric SMILES: CCOP(=O)([C@H](CC1=CC=CC=C1)NC(=O)[C@H](C(C)C)NC(=O)OCC2=CC=CC=C2)C(C(CC3=CC=CC=C3)NC(=O)[C@H](C(C)C)NC(=O)OCC4=CC=CC=C4)O

Technology Process of benzyl N-[(1S)-1-[[1-benzyl-2-[[(1R)-1-[[(2S)-2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]-2-phenyl-ethyl]-ethoxy-phosphoryl]-2-hydroxy-ethyl]carbamoyl]-2-methyl-propyl]carbamate

There total 4 articles about benzyl N-[(1S)-1-[[1-benzyl-2-[[(1R)-1-[[(2S)-2-(benzyloxycarbonylamino)-3-methyl-butanoyl]amino]-2-phenyl-ethyl]-ethoxy-phosphoryl]-2-hydroxy-ethyl]carbamoyl]-2-methyl-propyl]carbamate 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: 70.0%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + (2-Amino-1-hydroxy-3-phenyl-propyl)-((R)-1-amino-2-phenyl-ethyl)-phosphinic acid ethyl ester (146063-33-4) → [2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-1-hydroxy-3-phenyl-propyl]-[1-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-2-phenyl-ethyl]-phosphinic acid ethyl ester (146063-29-8)

Guidance literature:

With O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate;

DOI:10.1016/S0040-4039(00)61002-X

Reference yield:

benzyl (1S)-(1-formyl-2-phenylethyl)carbamate (59830-60-3) → [2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-1-hydroxy-3-phenyl-propyl]-[1-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-2-phenyl-ethyl]-phosphinic acid ethyl ester (146063-29-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 47 percent / NEt₃ / CHCl₃

2: 87 percent / H₂ / Pd/C

3: 70 percent / O-<(ethoxycarbonyl)cyanomethylenamino>-N,N,N',N'-tetramethyluroniumtetrafluoro-borate (TOTU)

With O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate; hydrogen; triethylamine; palladium on activated charcoal; In chloroform;

DOI:10.1016/S0040-4039(00)61002-X

Reference yield:

Cbz-(R)-α-amino-phosphinic acid ethylester (115961-51-8,146144-34-5) → [2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-1-hydroxy-3-phenyl-propyl]-[1-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-2-phenyl-ethyl]-phosphinic acid ethyl ester (146063-29-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 47 percent / NEt₃ / CHCl₃

2: 87 percent / H₂ / Pd/C

3: 70 percent / O-<(ethoxycarbonyl)cyanomethylenamino>-N,N,N',N'-tetramethyluroniumtetrafluoro-borate (TOTU)

With O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate; hydrogen; triethylamine; palladium on activated charcoal; In chloroform;

DOI:10.1016/S0040-4039(00)61002-X

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

(2-Amino-1-hydroxy-3-phenyl-propyl)-((R)-1-amino-2-phenyl-ethyl)-phosphinic acid ethyl ester

benzyl (1S)-(1-formyl-2-phenylethyl)carbamate

Cbz-(R)-α-amino-phosphinic acid ethylester

Downstream raw materials:

[2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-1-hydroxy-3-phenyl-propyl]-[1-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-2-phenyl-ethyl]-phosphinic acid