(3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<4'-(acetyloxy)butyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Base Information

Chemical Name:(3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<4'-(acetyloxy)butyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
CAS No.:136707-39-6
Molecular Formula:C₃₀H₃₁NO₆
Molecular Weight:501.579
Hs Code.:

Synonyms:(3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<4'-(acetyloxy)butyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

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Chemical Property of (3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<4'-(acetyloxy)butyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

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Technology Process of (3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<4'-(acetyloxy)butyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

There total 2 articles about (3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<4'-(acetyloxy)butyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-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: 80.6%

: 127-09-3
sodium acetate

: 136707-37-4
(3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(4'-iodobutyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

: 136707-39-6
(3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<4'-(acetyloxy)butyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Guidance literature:: In N,N-dimethyl-formamide; at 80 ℃; for 4h;
DOI:10.1021/ja00024a038

Reference yield:

: 105228-46-4,335159-14-3
(5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

: 136707-39-6
(3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<4'-(acetyloxy)butyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 78.6 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

2: 80.6 percent / dimethylformamide / 4 h / 80 °C

With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide;
DOI:10.1021/ja00024a038

Reference yield:

: 136707-39-6
(3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<4'-(acetyloxy)butyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

: 136707-47-6
(2R)-2-(tert-butyloxycarbonyl)amino-6-<(p-methoxybenzyl)thio>hexanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: H₂ / PdCl₂ / tetrahydrofuran; ethanol / 20 h / 2585.7 Torr

2: 1 N HCl / 2 h / Heating

3: 83 percent / Et₃N, DMAP / H₂O; acetonitrile / 24 h

4: 93.8 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h

5: 1.) NaOEt / 1.) EtOH, 20 min, 2.) EtOH, THF, 45 min

6: 91.3 percent / LiOH*H₂O / ethanol / 15 h

With hydrogenchloride; dmap; lithium hydroxide; hydrogen; sodium ethanolate; triethylamine; palladium dichloride; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ja00024a038