XK 263

Base Information

• Chemical Name: XK 263
• CAS No.: 153244-86-1
• Molecular Formula: C41H38 N2 O3
• Molecular Weight: 606.752
• Mol file: 153244-86-1.mol

Synonyms:2H-1,3-Diazepin-2-one,hexahydro-5,6-dihydroxy-1,3-bis(2-naphthalenylmethyl)-4,7-bis(phenylmethyl)-,[4R-(4a,5a,6b,7b)]-; XK 263

Chemical Property of XK 263

Chemical Property:

• Vapor Pressure: 2.24E-28mmHg at 25°C
• Boiling Point: 819°Cat760mmHg
• Flash Point: 449.1°C
• PSA: 64.01000
• Density: 1.268g/cm³
• LogP: 7.25100

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of XK 263

There total 7 articles about XK 263 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:

(4R,5S,6S,7R)-4,7-Dibenzyl-1,3-bis-naphthalen-2-ylmethyl-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]diazepan-2-one (1054639-78-9) → (4R,5S,6S,7R)-4,7-Dibenzyl-5,6-dihydroxy-1,3-bis-naphthalen-2-ylmethyl-[1,3]diazepan-2-one (153244-86-1)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; methanol;

DOI:10.1021/jm9602571

Reference yield:

(4R,5S,6S,7R)-hexahydro-5,6-bis[2-(trimethylsilyl)ethoxymethoxy]-4,7-bis(phenylmethyl)-2H-1,3-diazepin-2-one (153181-22-7) → (4R,5S,6S,7R)-4,7-Dibenzyl-5,6-dihydroxy-1,3-bis-naphthalen-2-ylmethyl-[1,3]diazepan-2-one (153244-86-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, RT, 10 min, 2.) DMF, 70 deg C, 5-7 h

2: 1 M HCl/ether / methanol / 12 h / Ambient temperature

With hydrogenchloride; diethyl ether; sodium hydride; In methanol;

DOI:10.1021/ja972357h

Reference yield:

N-(benzyloxycarbonyl)-D-phenylalaninol (58917-85-4) → (4R,5S,6S,7R)-4,7-Dibenzyl-5,6-dihydroxy-1,3-bis-naphthalen-2-ylmethyl-[1,3]diazepan-2-one (153244-86-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) oxalyl chloride, DMSO, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) CH₂Cl₂, -70 deg C, 2 h

2: 55 percent / VCl₃*(THF)3, Zn / CH₂Cl₂

3: 91 percent / diisopropylethylamine / dimethylformamide / 48 h / 50 °C

4: 52 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol

5: 1.) NaH / 1.) DMF, 15 min, 2.) DMF, a) 0 deg C, 15 min, b) RT, 2 h

6: HCl / methanol; dioxane

With hydrogenchloride; oxalyl dichloride; Vanadium (III) chloride-(tris-tetrahydrofuran); hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm9602571

upstream raw materials:

(4R,5S,6S,7R)-4,7-Dibenzyl-1,3-bis-naphthalen-2-ylmethyl-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]diazepan-2-one

2-bromomethylnaphthyl bromide

(4R,5S,6S,7R)-hexahydro-5,6-bis[2-(trimethylsilyl)ethoxymethoxy]-4,7-bis(phenylmethyl)-2H-1,3-diazepin-2-one

N-(benzyloxycarbonyl)-D-phenylalaninol

Downstream raw materials:

Acetic acid (4R,5R,6R)-4-benzyl-1,3-bis-naphthalen-2-ylmethyl-2-oxo-6-phenethyl-hexahydro-pyrimidin-5-yl ester

(4R,5S,6R)-4-Benzyl-5-hydroxy-1,3-bis-naphthalen-2-ylmethyl-6-((E)-styryl)-tetrahydro-pyrimidin-2-one

(4R,5S,6S,7R)-hexahydro-5-(mesyloxy)-6-hydroxy-1,3-bis-<2-naphthylmethyl>-4,7-bis--2H-1,3-diazepin-2-one

Acetic acid (4R,5S,6S)-4-benzyl-6-((S)-1-bromo-2-phenyl-ethyl)-1,3-bis-naphthalen-2-ylmethyl-2-oxo-hexahydro-pyrimidin-5-yl ester

Refernces

• 1、 Lam, Patrick Y. S.,Ru, Yu,Jadhav, Prabhakar K.,Aldrich, Paul E.,DeLucca, George V.,Eyermann, Charles J.,Chang, Chong-Hwan,Emmett, George,Holler, Edward R.,Daneker, Wayne F.,Li, Liangzhu,Confalone, Pat N.,McHugh, Robert J.,Han, Qi,Li, Renhua,Markwalder, Jay A.,Seitz, Steven P.,Sharpe, Thomas R.,Bacheler, Lee T.,Rayner, Marlene M.,Klabe, Ronald M.,Shum, Linyee,Winslow, Dean L.,Kornhauser, David M.,Jackson, David A.,Erickson-Viitanen, Susan,Hodge, C. Nicholas. "Cyclic HIV protease inhibitors: Synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas". . p. 3514 - 3525. Retrieved 2007/10/03.