(4R,5S,6S,7R)-1,3,4,7-tetrabenzyl-5,6-dihydroxy-1,3-diazepan-2-one

Base Information

• Chemical Name: (4R,5S,6S,7R)-1,3,4,7-tetrabenzyl-5,6-dihydroxy-1,3-diazepan-2-one
• CAS No.: 153223-23-5
• Molecular Formula: C33H34 N2 O3
• Molecular Weight: 506.645
• Mol file: 153223-23-5.mol

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

Chemical Property of (4R,5S,6S,7R)-1,3,4,7-tetrabenzyl-5,6-dihydroxy-1,3-diazepan-2-one

Chemical Property:

• Vapor Pressure: 1.78E-20mmHg at 25°C
• Boiling Point: 698.4°Cat760mmHg
• PKA: 14.17±0.70(Predicted)
• Flash Point: 376.2°C
• PSA: 64.01000
• Density: 1.235g/cm³
• LogP: 4.94460

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4R,5S,6S,7R)-1,3,4,7-tetrabenzyl-5,6-dihydroxy-1,3-diazepan-2-one

There total 21 articles about (4R,5S,6S,7R)-1,3,4,7-tetrabenzyl-5,6-dihydroxy-1,3-diazepan-2-one 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: 79.0%

(4R,5S,6S,7R)-hexahydro-5,6-isopropylidenedioxy-4,7-bis(phenylmethyl)-2H-diazapin-2-one (180302-24-3) → XL075 (153223-23-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 3h; Ambient temperature;

DOI:10.1021/jo980980u

Reference yield:

Cbz-D-Phe (2448-45-5) → XL075 (153223-23-5)

Guidance literature:

Multi-step reaction with 9 steps

1: N-methylmorpholine / CH₂Cl₂ / 0.25 h / 0 °C

2: CH₂Cl₂ / 3 h / Ambient temperature

3: LAH / tetrahydrofuran / 1 h / 0 - 25 °C

4: VCl₃(THF)3, Zn-Cu / CH₂Cl₂ / 3 h / Ambient temperature

5: N,N-diisopropylethylamine / dimethylformamide / 18 h / Ambient temperature

6: cyclohexene / 20percent Pd(OH)2/C / ethanol / 18 h / Heating

7: CH₂Cl₂ / 18 h / Heating

8: NaH / dimethylformamide / 18 h / Ambient temperature

9: 4 N HCl / methanol; dioxane / 18 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; lithium aluminium tetrahydride; Vanadium (III) chloride-(tris-tetrahydrofuran); copper; sodium hydride; N-ethyl-N,N-diisopropylamine; zinc; cyclohexene; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm960083n

Reference yield:

N-(benzyloxycarbonyl)-D-phenylalaninal (63219-70-5) → XL075 (153223-23-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 55 percent / VCl₃*(THF)3, Zn / CH₂Cl₂

2: 91 percent / diisopropylethylamine / dimethylformamide / 48 h / 50 °C

3: 52 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol

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

5: HCl / methanol; dioxane

With hydrogenchloride; Vanadium (III) chloride-(tris-tetrahydrofuran); hydrogen; sodium hydride; 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)-1,3,4,7-Tetrabenzyl-5,6-bis-(2-trimethylsilanyl-ethoxymethoxy)-[1,3]diazepan-2-one

(4R,5S,6S,7R)-hexahydro-5,6-isopropylidenedioxy-4,7-bis(phenylmethyl)-2H-diazapin-2-one

N-benzyl hydroxylalmine

(2R,3S,4S,5R)-2,5-bis(phenylmethylamino)-3,4-O-isopropylidene-1,6-diphenyl-3,4-hexanediol

Downstream raw materials:

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

Refernces

• 1、 Nugiel,Jacobs,Worley,Patel,Kaltenbach III,Meyer,Jadhav,De Lucca,Smyser,Klabe,Bacheler,Rayner,Seitz. "Preparation and structure-activity relationship of novel P1/P1'- substituted cyclic urea-based human immunodeficiency virus type-1 protease inhibitors". . p. 2156 - 2169. Retrieved 2007/10/03.