Thiazol-5-ylmethyl ((2S,3S,5S)-5-amino-3-hydroxy-1,6-diphenylhexan-2-yl)carbamate

Base Information

• Chemical Name: Thiazol-5-ylmethyl ((2S,3S,5S)-5-amino-3-hydroxy-1,6-diphenylhexan-2-yl)carbamate
• CAS No.: 144164-11-4
• Molecular Formula: C23H27N3O3S
• Molecular Weight: 425.552
• DSSTox Substance ID: DTXSID10455244
• Nikkaji Number: J1.080.353E
• Wikidata: Q72442526
• Mol file: 144164-11-4.mol

Synonyms:144164-11-4;Thiazol-5-ylmethyl ((2S,3S,5S)-5-amino-3-hydroxy-1,6-diphenylhexan-2-yl)carbamate;(2S,3S,5S)-5-AMINO-2-(N-((5-THIAZOLYL)-METHOXYCARBONYL)AMINO)-1,6-DIPHENYL-3-HYDROXYHEXANE;2S,3S,5S-5-Amino-2-[N-[[(5-thiozolyl)methoxy]carbonyl]amino]-1,6-diphenyl-3-hydroxyhexane;(2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane;1,3-THIAZOL-5-YLMETHYL N-[(2S,3S,5S)-5-AMINO-3-HYDROXY-1,6-DIPHENYLHEXAN-2-YL]CARBAMATE;SCHEMBL893198;DTXSID10455244;BCP22733;MFCD07367634;AKOS015896455;AC-8900;CS-T-48131;DS-18504;CS-0149754;C72725;A808185;J-007926;J-524904;(1,3-Thiazol-5-yl)methyl [(2S,3S,5S)-5-amino-3-hydroxy-1,6-diphenylhexan-2-yl]carbamate;(2S,3S,5S)-1,6-Diphenyl-2-[(5-thiazolyl)methoxycarbonylamino]-5-aminohexane-3-ol;(2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6diphenyl-3-hydroxyhexane;1,3-thiazol-5-ylmethyl (1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentylcarbamate;1,3-thiazol-5-ylmethyl(1s,2s,4s)-4-amino-1-benzyl-2-hydroxy-5-phenylpentylcarbamate;Thiazol-5-ylmethyl [(1S,2S,4S)-4-Amino-1-benzyl-2-hydroxy-5-phenylpentyl]carbamate;Thiazol-5-ylmethyl((2S,3S,5S)-5-amino-3-hydroxy-1,6-diphenylhexan-2-yl)carbamate;(2 S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane;(2S,3S,5S )-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane;(2S,3S,5S)-5-amino-2-(N-((5-thiazolyl) methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane;(2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino )-1,6-diphenyl-3- hydroxyhexane;(2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)- 1,6-diphenyl-3-hydroxyhexane;(2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1.6-diphenyl-3-hydroxyhexane;Carbamic acid, N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]-, 5-thiazolylmethyl ester

Chemical Property of Thiazol-5-ylmethyl ((2S,3S,5S)-5-amino-3-hydroxy-1,6-diphenylhexan-2-yl)carbamate

Chemical Property:

• Appearance/Colour: Light yellow oil
• Vapor Pressure: 4.17E-18mmHg at 25°C
• Refractive Index: 1.619
• Boiling Point: 656.1 °C at 760 mmHg
• PKA: 11.48±0.46(Predicted)
• Flash Point: 350.6 °C
• PSA: 125.71000
• Density: 1.251 g/cm³
• LogP: 4.39280
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 425.17731291
• Heavy Atom Count: 30
• Complexity: 498

Purity/Quality:

99% ^*data from raw suppliers

2S,3S,5S-5-Amino-2-[N-[[(5-thiozolyl)methoxy]carbonyl]amino]-1,6-diphenyl-3-hydroxyhexane ^*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(CC(C(CC2=CC=CC=C2)NC(=O)OCC3=CN=CS3)O)N
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C[C@@H]([C@H](CC2=CC=CC=C2)NC(=O)OCC3=CN=CS3)O)N
• Uses: An intermediate in the synthesis of Ritonavir.

Technology Process of Thiazol-5-ylmethyl ((2S,3S,5S)-5-amino-3-hydroxy-1,6-diphenylhexan-2-yl)carbamate

There total 9 articles about Thiazol-5-ylmethyl ((2S,3S,5S)-5-amino-3-hydroxy-1,6-diphenylhexan-2-yl)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: 98.2%

(2S,3S,5S)-5-(t-butyloxycarbonylamino)-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane (162849-95-8) → (2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane (144164-11-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 3h;

Reference yield: 16.0%

(2S,3S,5S)-3-hydroxy-2,5-bisamino-1,6-diphenylhexane (144163-44-0) + ((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate (144163-97-3) → (2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane (144164-11-4) + (2S,3S,5S)-2-amino-5-carbonyl>amino>-1,6-diphenyl-3-hydroxyhexane

Guidance literature:

In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1021/jm970636+

Reference yield:

ritonavir (155213-67-5) → (2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane (144164-11-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 65 ℃; for 20h;

upstream raw materials:

((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate

(4S,6S,1'S)-6-(1-amino-2-phenylethyl)-4-benzyl-2-phenyl-3-aza-2-bora-1-oxacyclohexane

(2S,3S,5S)-3-hydroxy-2,5-bisamino-1,6-diphenylhexane

(2S,3S,5S)-5-(t-butyloxycarbonylamino)-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane

Downstream raw materials:

ritonavir

C₃₇H₄₂⁽²⁾H₆N₆O₅S₂

(2S,3S,5S)-2-(N-((5-Thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-5-(2S-(1-imidazolidin-2-onyl)-3,3-dimethyl butanoyl)amino-1,6-diphenylhexane

(2S,3S,5S)-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-5-((2S-(1-imidazolidin-2-onyl)-3-methyl-butanoyl)-amino)-3-hydroxy-1,6-diphenylhexane

Refernces

• 1、 -. "A method of preparing anti HIV drug ritonavir". Paragraph 0016; 0017; 0018; 0025. . Retrieved 2017/08/25.
• 2、 -. "METHOD OF DETECTION OF ANALYTE ACTIVE FORMS AND DETERMINATION OF THE ABILITY OF SUBSTANCES TO BIND INTO ANALYTE ACTIVE SITES". Page/Page column 67; 68. . Retrieved 2016/04/09.