(4R,6S,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-aminoethyl)-1,3-oxazinan-2-one

Base Information

• Chemical Name: (4R,6S,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-aminoethyl)-1,3-oxazinan-2-one
• CAS No.: 624739-12-4
• Molecular Formula: C₁₇H₂₄N₂O₄
• Molecular Weight: 320.389
• Mol file: 624739-12-4.mol

Synonyms:(4R,6S,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-aminoethyl)-1,3-oxazinan-2-one

Chemical Property of (4R,6S,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-aminoethyl)-1,3-oxazinan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,6S,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-aminoethyl)-1,3-oxazinan-2-one

There total 10 articles about (4R,6S,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-aminoethyl)-1,3-oxazinan-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:

(4R,6R,1'S,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-iodoethyl)-1,3-oxazinan-2-one (624739-02-2) → (4R,6S,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-aminoethyl)-1,3-oxazinan-2-one (624739-12-4)

Guidance literature:

(4R,6R,1'S,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-iodoethyl)-1,3-oxazinan-2-one; With sodium azide; In N,N-dimethyl-formamide; at 110 ℃; for 5h;

With hydrogen; palladium on activated charcoal; In methanol; for 28h; under 760 Torr;

DOI:10.1039/b404962d

Reference yield:

(4R,6R,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-azidoethyl)-1,3-oxazin-2-one (785790-12-7) → (4R,6S,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-aminoethyl)-1,3-oxazinan-2-one (624739-12-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 40h; under 760.051 Torr;

DOI:10.1039/b305740b

Reference yield:

(3R,5E,αR)-methyl 3-(N-[α-methylbenzyl]amino)-hept-5-enoate (624739-11-3) → (4R,6S,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-aminoethyl)-1,3-oxazinan-2-one (624739-12-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 17 h / 20 °C

2.1: I₂ / CH₂Cl₂ / 4 h / 0 °C

3.1: aq. NaN₃ / dimethylformamide / 5 h / 110 °C

3.2: 1.24 g / H₂ / Pd/C / methanol / 28 h / 760 Torr

With dmap; sodium azide; iodine; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b404962d

upstream raw materials:

(4R,6R,1'R,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-azidoethyl)-1,3-oxazin-2-one

(4R,6R,1'S,αR)-3-(α-methylbenzyl)-4-(methoxycarbonylmethyl)-6-(1'-iodoethyl)-1,3-oxazinan-2-one

(3R,5E,αR)-methyl 3-(N-methoxycarbonyl-N-α-methylbenzylamino)hept-5-enoate

(3R,5E,αR)-methyl 3-(N-tert-butoxycarbonyl-N-α-methylbenzylamino)hept-5-enoate

Downstream raw materials:

(4R,6R,1'R,αR)-3-(N-α-methylbenzyl)-4-(carboxymethyl)-6-(1'-aminoethyl)-1,3-oxazin-2-one

(3R,5R,6R,αR)-3-(N-α-methylbenzylamino)-5-hydroxy-6-aminoheptanoic acid

sperabillin B

sperabillin D