(2R,3R,5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-3-ethyl-2,3,5,6-tetrahydro-4H-1,4-oxazine

Base Information

Chemical Name:(2R,3R,5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-3-ethyl-2,3,5,6-tetrahydro-4H-1,4-oxazine
CAS No.:213686-75-0
Molecular Formula:C₂₈H₂₉NO₅
Molecular Weight:459.542
Hs Code.:

Synonyms:(2R,3R,5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-3-ethyl-2,3,5,6-tetrahydro-4H-1,4-oxazine

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Chemical Property of (2R,3R,5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-3-ethyl-2,3,5,6-tetrahydro-4H-1,4-oxazine

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Technology Process of (2R,3R,5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-3-ethyl-2,3,5,6-tetrahydro-4H-1,4-oxazine

There total 2 articles about (2R,3R,5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-3-ethyl-2,3,5,6-tetrahydro-4H-1,4-oxazine 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: 49.0%

: 108-24-7
acetic anhydride

: 213686-57-8
(3R,5R,6S)-4-benzyloxycarbonyl-5,6-diphenyl-3-ethyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

: (2S,3R,5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-3-ethyl-2,3,5,6-tetrahydro-4H-1,4-oxazine

: 213686-75-0
(2R,3R,5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-3-ethyl-2,3,5,6-tetrahydro-4H-1,4-oxazine

Guidance literature:: (3R,5R,6S)-4-benzyloxycarbonyl-5,6-diphenyl-3-ethyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one; With diisobutylaluminium hydride; In hexane; dichloromethane; water; at -78 ℃; for 1.5h;

acetic anhydride; With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 0.5h;
DOI:10.1016/S0040-4020(98)00495-5

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

: 213686-75-0
(2R,3R,5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-3-ethyl-2,3,5,6-tetrahydro-4H-1,4-oxazine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 80 percent / HMPA; NaN(TMS)2 / tetrahydrofuran / 0.67 h / -78 °C

2.1: DIBAH / CH₂Cl₂; hexane; H₂O / 1.5 h / -78 °C

2.2: 49 percent / DMAP; Et₃N / CH₂Cl₂ / 0.5 h / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; water; 1.1: Alkylation / 2.1: Reduction / 2.2: Acetylation;
DOI:10.1016/S0040-4020(98)00495-5