59JB7S9VY9

Base Information

• Chemical Name: 59JB7S9VY9
• CAS No.: 158512-24-4
• Molecular Formula: C24H27 N O3
• Molecular Weight: 377.483
• UNII: 59JB7S9VY9
• Nikkaji Number: J1.827.059E
• Mol file: 158512-24-4.mol

Synonyms:59JB7S9VY9;158512-24-4;(2R)-1-((3aS,8aR)-2,2-Dimethyl-8,8a-dihydro-2H-indeno(1,2-d)oxazol-3(3ah)-yl)-2-((2S)-oxiranylmethyl)-3-phenylpropan-1-one.;(3aS,8aR)-3-(4,5-Anhydro-2,3-dideoxy-2-(phenylmethyl)-D-erythro-pentonoyl)-3,3a,8,8a-tetrahydro-2,2-dimethyl-2H-indeno(1,2-d)oxazole;2H-Indeno(1,2-d)oxazole, 3-(4,5-anhydro-2,3-dideoxy-2-(phenylmethyl)-D-erythro-pentonoyl)-3,3a,8,8a-tetrahydro-2,2-dimethyl-, (3aS,8aR)-;N-(N,O-Isopropylidene-(2R)-hydroxy indan-(1S)-yl)-(2R)-benzyl-(4S,5)-epoxy pentanamide;UNII-59JB7S9VY9;(2R)-1-[(3aS)-2,2-Dimethyl-3,3aalpha,8,8aalpha-tetrahydro-2H-indeno[1,2-d]oxazole-3-yl]-2-[[(S)-oxirane-2beta-yl]methyl]-3-phenyl-1-propanone;2-Benzyl-1-(2,2-dimethyl-8,8 alpha -dihydro-3 alpha ,H-indeno[1,2-d]oxazol-3yl)-3-oxiranyl-propan-1-one;2H-INDENO(1,2-D)OXAZOLE, 3,3A,8,8A-TETRAHYDRO-2,2-DIMETHYL-3-(2-(OXIRANYLMETHYL)-1-OXO-3-PHENYLPROPYL)-, (3AS-(3(S*(R*)),3A.ALPHA.,8A.ALPHA.))-;2H-Indeno(1,2-d)oxazole, 3,3a,8,8a-tetrahydro-2,2-dimethyl-3-(2-(oxiranylmethyl)-1-oxo-3-phenylpropyl)-, (3as-(3(S*(R*)),3aalpha,8aalpha))-;2H-Indeno[1,2-D]oxazole,3-(4,5-anhydro-2,3-dideoxy-2-(phenylmethyl)-d-erythro-pentonoyl)-3,3a,8,8a-tetrahydro-2,2-dimethyl-,(3as,8ar)-(9ci)

Chemical Property of 59JB7S9VY9

Chemical Property:

• Vapor Pressure: 1.62E-12mmHg at 25°C
• Boiling Point: 558.7°C at 760 mmHg
• Flash Point: 291.7°C
• PSA: 42.07000
• Density: 1.183g/cm³
• LogP: 3.83300
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 377.19909372
• Heavy Atom Count: 28
• Complexity: 584

Purity/Quality:

98% ^*data from raw suppliers

2-Benzyl-1-(2,2-dimethyl-8,8α-dihydro-3α,H-indeno[1,2-d]oxazol-3yl)-3-oxiranyl-propan-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(N(C2C(O1)CC3=CC=CC=C23)C(=O)C(CC4CO4)CC5=CC=CC=C5)C
• Isomeric SMILES: CC1(N([C@@H]2[C@H](O1)CC3=CC=CC=C23)C(=O)[C@@H](C[C@H]4CO4)CC5=CC=CC=C5)C
• Uses: An intermediate in the synthesis of Indinavir.

Technology Process of 59JB7S9VY9

There total 8 articles about 59JB7S9VY9 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: 92.0%

(2R,4S)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-4-hydroxy-5-iodo-pentan-1-one (165883-49-8) → (R)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-(S)-oxiranyl-propan-1-one (158512-24-4)

Guidance literature:

With sodium methylate;

DOI:10.1016/S0040-4039(96)02445-8

Reference yield: 86.0%

(S)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-pent-4-en-1-one (150323-06-1) → (R)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-(S)-oxiranyl-propan-1-one (158512-24-4)

Guidance literature:

With sodium bromide; constant current electrolysis (undivided electrochemical cell, MeCN/H₂₀);

DOI:10.1016/S0040-4039(96)02445-8

Reference yield:

(2R,4S)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-4-hydroxy-5-iodo-pentan-1-one (165883-49-8) → (R)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-(R)-oxiranyl-propan-1-one (158380-44-0) + (R)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-3-(S)-oxiranyl-propan-1-one (158512-24-4)

Guidance literature:

With sodium methylate; In methanol; at 25 ℃; for 1h; Yield given. Yields of byproduct given;

DOI:10.1016/0040-4020(95)01114-5

upstream raw materials:

(S)-epichlorohydrin

(3aS,8aR)-2,2-dimethyl-3-(3-phenylpropanoyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3]oxazole

(S)-Glycidyl tosylate

(S)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-pent-4-en-1-one

Downstream raw materials:

(2R,4S)-2-Benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-4-hydroxy-5-(2-methoxy-phenyl)-pentan-1-one

[14C]-N-Dealkyl Indinavir

indinavir

(2R,4S)-2-Benzyl-5-(2-tert-butylsulfamoyl-phenyl)-4-hydroxy-pentanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide

Refernces

• 1、 Maligres,Weissman,Upadhyay,Cianciosi,Reamer,Purick,Sager,Rossen,Eng,Askin,Volante,Reider. "Cyclic imidate salts in acyclic stereochemistry: Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides". . p. 3327 - 3338. Retrieved 2007/10/03.
• 2、 Askin, David,Eng, Kan K.,Rossen, Kai,Purick, Robert M.,Wells, Kenneth M.,et al.. "Highly Diastereoselective Reaction of a Chiral, Non-Racemic Amide Enolate with (S)-Glycidyl Tosylate. Synthesis of the Orally Active HIV-1 Protease Inhibitor L-735,524". . p. 673 - 676. Retrieved 2007/10/02.