(4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-di(prop-2-en-1-yl)-1,3-diazepan-2-one

Base Information

• Chemical Name: (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-di(prop-2-en-1-yl)-1,3-diazepan-2-one
• CAS No.: 153223-14-4
• Molecular Formula: C25H30 N2 O3
• Molecular Weight: 406.5173
• Mol file: 153223-14-4.mol

Synonyms:2H-1,3-Diazepin-2-one,hexahydro-5,6-dihydroxy-4,7-bis(phenylmethyl)-1,3-di-2-propenyl-,(4R,5S,6S,7R)- (9CI); 2H-1,3-Diazepin-2-one,hexahydro-5,6-dihydroxy-4,7-bis(phenylmethyl)-1,3-di-2-propenyl-, [4R-(4a,5a,6b,7b)]-

Chemical Property of (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-di(prop-2-en-1-yl)-1,3-diazepan-2-one

Chemical Property:

• Vapor Pressure: 6.1E-14mmHg at 25°C
• Boiling Point: 572.4°C at 760 mmHg
• Flash Point: 300°C
• Density: 1.155g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-di(prop-2-en-1-yl)-1,3-diazepan-2-one

There total 8 articles about (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-di(prop-2-en-1-yl)-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:

N-(benzyloxycarbonyl)-D-phenylalaninol (58917-85-4) → (4R,5S,6S,7R)-1,3-Diallyl-4,7-dibenzyl-5,6-dihydroxy-[1,3]diazepan-2-one (153223-14-4)

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

Reference yield:

N-(benzyloxycarbonyl)-D-phenylalaninal (63219-70-5) → (4R,5S,6S,7R)-1,3-Diallyl-4,7-dibenzyl-5,6-dihydroxy-[1,3]diazepan-2-one (153223-14-4)

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

Reference yield:

((1S,2R,3S,4R)-1-Benzyl-4-benzyloxycarbonylamino-2,3-dihydroxy-5-phenyl-pentyl)-carbamic acid benzyl ester (183814-19-9) → (4R,5S,6S,7R)-1,3-Diallyl-4,7-dibenzyl-5,6-dihydroxy-[1,3]diazepan-2-one (153223-14-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / diisopropylethylamine / dimethylformamide / 48 h / 50 °C

2: 52 percent / H₂ / 10percent Pd/C / ethyl acetate; methanol

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

4: HCl / methanol; dioxane

With hydrogenchloride; hydrogen; sodium hydride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm9602571

upstream raw materials:

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

N-(benzyloxycarbonyl)-D-phenylalaninol

N-(benzyloxycarbonyl)-D-phenylalaninal

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

Downstream raw materials:

(4R,5S,6S,7R)-4,7-Dibenzyl-5,6-dihydroxy-1,3-bis-(3-hydroxy-propyl)-[1,3]diazepan-2-one