(2S,3S,5S)-5-(tert-Butoxycarbonylamino)-2-(N-5-thiazolylmethoxycarbonyl)amino-1,6-diphenyl-3-hydroxyhexane

Base Information

• Chemical Name: (2S,3S,5S)-5-(tert-Butoxycarbonylamino)-2-(N-5-thiazolylmethoxycarbonyl)amino-1,6-diphenyl-3-hydroxyhexane
• CAS No.: 162849-95-8
• Molecular Formula: C28H35N3O5S
• Molecular Weight: 525.669
• Mol file: 162849-95-8.mol

Synonyms:(2S,3S,5S)-5-(tert-Butoxycarbonylamino)-2-(N-5-thiazolylmethoxycarbonyl)amino-1,6-diphenyl-3-hydroxyhexane

Chemical Property of (2S,3S,5S)-5-(tert-Butoxycarbonylamino)-2-(N-5-thiazolylmethoxycarbonyl)amino-1,6-diphenyl-3-hydroxyhexane

Chemical Property:

• Boiling Point: 722.3±60.0 °C(Predicted)
• PKA: 11.48±0.46(Predicted)
• PSA: 138.02000
• Density: 1.219
• LogP: 5.64940
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

N-[(1S,2S,4S)-4-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]carbamicAcid5-ThiazolylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-[(1S,2S,4S)-4-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]carbamic Acid 5-Thiazolylmethyl Ester (Ritonavir EP Impurity J) is an intermediate in the synthesis of Ritonavir (R535000), a selective HIV protease inhibitor used for the treatment of HIV infections and AIDS.

Technology Process of (2S,3S,5S)-5-(tert-Butoxycarbonylamino)-2-(N-5-thiazolylmethoxycarbonyl)amino-1,6-diphenyl-3-hydroxyhexane

There total 4 articles about (2S,3S,5S)-5-(tert-Butoxycarbonylamino)-2-(N-5-thiazolylmethoxycarbonyl)amino-1,6-diphenyl-3-hydroxyhexane 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%

(2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane (144163-85-9) + ((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate (144163-97-3) → (2S,3S,5S)-5-(t-butyloxycarbonylamino)-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane (162849-95-8)

Guidance literature:

(2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane; ((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate; In acetonitrile; at 20 ℃; for 0.333333h;

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 48h;

Reference yield: 81.0%

(2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane (144163-85-9) + 5-(p-nitrophenyloxycarbonyloxymethyl)thiazole hydrochloride (154212-59-6) → (2S,3S,5S)-5-(t-butyloxycarbonylamino)-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane (162849-95-8)

Guidance literature:

In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0968-0896(02)00322-X

Reference yield:

(2S,3S,5S)-2-amino-3-hydroxy-5-tert-butoxycarbonylamino-1,6-diphenylhexane succinate (256328-84-4,183388-64-9) + 5-(p-nitrophenyloxycarbonyloxymethyl)thiazole hydrochloride (154212-59-6) → (2S,3S,5S)-5-(t-butyloxycarbonylamino)-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane (162849-95-8)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate; at 20 - 60 ℃; for 9h;

upstream raw materials:

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

5-(p-nitrophenyloxycarbonyloxymethyl)thiazole hydrochloride

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

(2S,3S,5S)-2-amino-3-hydroxy-5-tert-butoxycarbonylamino-1,6-diphenylhexane succinate

Downstream raw materials:

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

1,6-diphenyl-5(S)-tert-butoxycarbonylamino-2(S)-(5-thiazolemethoxy)carbonylamino-hexane

3(S)-imidazolecarbothioic acid 1,6-diphenyl-5(S)-tert-butoxycarbonylamino-2(S)-(5-thiazolemethoxycarbonylamino)hexane, ester

(2S,3S,5S)-3-[O-[N-[N-methyl-N-[(2-isopropyl-4-thiazolyl)methyl]amino]carbonyl]-L-valyloxy]-5-[N-[(tert-butyloxy)carbonyl]amino]-2-[N-[(5-thiazolyl)methoxycarbonyl]amino]-1,6-diphenyl-3-hydroxyhexane

Refernces

• 1、 -. "Ritonavir selenazole derivative with anti-HIV (Human Immunodeficiency Virus)-I activity and synthesis method". Paragraph 0026; 0034. . Retrieved 2018/04/01.
• 2、 -. "CYTOCHROME P450 OXIDASE INHIBITORS AND USES THEREOF". Page/Page column 96. . Retrieved 2008/06/13.