benzyl ((2R,3R)-4-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-yl)carbamate

Base Information

• Chemical Name: benzyl ((2R,3R)-4-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-yl)carbamate
• CAS No.: 159878-04-3
• Molecular Formula: C32H45N3O4S
• Molecular Weight: 567.793
• DSSTox Substance ID: DTXSID10449901
• Nikkaji Number: J918.688C
• Wikidata: Q76416330
• Mol file: 159878-04-3.mol

Synonyms:159878-04-3;[3S-(3S,4aS,8aS,2'R,3'R)]-2-[3'-N-CBz-amino-2'-hydroxy-4'-(phenyl)thio]butyldecahydroisoquinoline-3-N-t-butylcarboxamide;benzyl ((2R,3R)-4-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-yl)carbamate;Benzyl N-[(2R,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-phenylsulfanylbutan-2-yl]carbamate;Carbamic acid, N-[(1R,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-[(phenylthio)methyl]propyl]-, phenylmethyl ester;SCHEMBL14583747;DTXSID10449901;CADGDESSNWSRRZ-RIVMDFSBSA-N;AKOS030241892;AG-1357

Chemical Property of benzyl ((2R,3R)-4-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-yl)carbamate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 130-134 C
• Boiling Point: 767.753°C at 760 mmHg
• Flash Point: 418.122°C
• PSA: 123.18000
• Density: 1.201g/cm³
• LogP: 6.21260
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 567.31307810
• Heavy Atom Count: 40
• Complexity: 794

Purity/Quality:

98.5% ^*data from raw suppliers

[3S-(3S,4aS,8aS,2’R,3’R)]-2-[3’-N-CBz-amino-2’-hydroxy-4’-(phenyl)thio]butyldecahydroisoquinoline-3-N-t-butylcarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)NC(=O)C1CC2CCCCC2CN1CC(C(CSC3=CC=CC=C3)NC(=O)OCC4=CC=CC=C4)O
• Isomeric SMILES: CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@H]([C@H](CSC3=CC=CC=C3)NC(=O)OCC4=CC=CC=C4)O
• Uses: An intermediate in the synthesis of Nelfinavir.

Technology Process of benzyl ((2R,3R)-4-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-yl)carbamate

There total 19 articles about benzyl ((2R,3R)-4-((3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-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: 86.0%

(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide (128019-40-9,149510-73-6,136465-81-1,168899-60-3) + (2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-2-methanesulfonyloxy-1-(4-nitrobenzoyloxy)butane (188923-26-4) → (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-(phenylthio)butyl]decahydroisoquinoline-3-carboxamide (159878-04-3)

Guidance literature:

With potassium carbonate; In methanol; water; at 60 ℃; for 7h;

DOI:10.1021/jo991793e

Reference yield:

(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide (128019-40-9,149510-73-6,136465-81-1,168899-60-3) + benzyl [(1R)-1-[(2S)-2-oxiranyl]-2-(phenylsulfanyl)ethyl]carbamate (163462-16-6) → (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-(phenylthio)butyl]decahydroisoquinoline-3-carboxamide (159878-04-3)

Guidance literature:

In isopropyl alcohol; at 40 ℃; for 4 - 24h; Heating / reflux;

Reference yield:

benzoic acid (65-85-0,8013-63-6) → (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-(phenylthio)butyl]decahydroisoquinoline-3-carboxamide (159878-04-3)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / Pd/C / propan-2-ol / 9 h / 60 °C

2: K₂CO₃ / toluene; H₂O / 3 h / 20 °C

3: Et₃N / toluene / 1.5 h / 10 °C

4: 1.93 kg / NaOH; Bu₄NBr / toluene; H₂O / 2.5 h / 55 °C

5: aq. HCl / methanol / 3.5 h / Heating

6: 2-picoline / ethyl acetate / 8.5 h / 5 - 10 °C

7: 1.31 kg / Et₃N / ethyl acetate / 0.5 h

8: 86 percent / K₂CO₃ / methanol; H₂O / 7 h / 60 °C

With α-picoline; hydrogenchloride; sodium hydroxide; tetrabutylammomium bromide; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In methanol; water; ethyl acetate; isopropyl alcohol; toluene; 1: Hydrogenolysis / 2: Condensation / 3: Condensation / 4: Substitution / 5: Hydrolysis / 6: Esterification / 7: Condensation / 8: Substitution;

DOI:10.1021/jo991793e

upstream raw materials:

(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide

(2R,3R)-3-benzyloxycarbonylamino-4-phenylthio-2-methanesulfonyloxy-1-(4-nitrobenzoyloxy)butane

((1R,2S)-2-Hydroxy-3-oxo-1-phenylsulfanylmethyl-propyl)-carbamic acid benzyl ester

benzyl chloroformate

Downstream raw materials:

nelfinavir

(3S,4AS,8AS)-2-((2R,3R)-3-amino-2-hydroxy-4-phenylthiobutyl)-decahydroisoquinoline-3-carboxylic acid t-butylamide