(3S,5S,6R)-4-(tert-butoxycarbonyl)-3-(dimethoxyphosphoryl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Base Information

• Chemical Name: (3S,5S,6R)-4-(tert-butoxycarbonyl)-3-(dimethoxyphosphoryl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
• CAS No.: 136328-42-2
• Molecular Formula: C₂₃H₂₈NO₇P
• Molecular Weight: 461.452

Synonyms:(3S,5S,6R)-4-(tert-butoxycarbonyl)-3-(dimethoxyphosphoryl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Chemical Property of (3S,5S,6R)-4-(tert-butoxycarbonyl)-3-(dimethoxyphosphoryl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Chemical Property:

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Technology Process of (3S,5S,6R)-4-(tert-butoxycarbonyl)-3-(dimethoxyphosphoryl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

There total 2 articles about (3S,5S,6R)-4-(tert-butoxycarbonyl)-3-(dimethoxyphosphoryl)-5,6-diphenyl-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:

tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate (112741-49-8,173397-90-5) → (3S,5S,6R)-4-(tert-butoxycarbonyl)-3-(dimethoxyphosphoryl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (136328-42-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NBS / CCl₄ / 1 h / Heating

2: tetrahydrofuran / 12 h / Heating

With N-Bromosuccinimide; In tetrahydrofuran; tetrachloromethane;

Reference yield:

(3S,5S,6R)-3-bromo-4(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (112741-51-2) + phosphorous acid trimethyl ester (121-45-9) → (3S,5S,6R)-4-(tert-butoxycarbonyl)-3-(dimethoxyphosphoryl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (136328-42-2)

Guidance literature:

In tetrahydrofuran; for 12h; Yield given; Heating;

Reference yield:

paraformaldehyde-d2 (1664-98-8,43094-80-0) + (3S,5S,6R)-4-(tert-butoxycarbonyl)-3-(dimethoxyphosphoryl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (136328-42-2) → (5S,6R)-4-(tert-butoxycarbonyl)-5,6-diphenyl-3-(<2H2>-methylidene)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (136328-50-2)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, RT, 1 h, 2.) THF, 24 h;

upstream raw materials:

(3S,5S,6R)-3-bromo-4(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

phosphorous acid trimethyl ester

tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate

Downstream raw materials:

(5S,6R)-4-(tert-butoxycarbonyl)-5,6-diphenyl-3-(<2H2>-methylidene)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

(E)-(5S,6R)-5,6-diphenyl-3-(4'-nitrobenzylidene)-4-(tert-butoxycarbonyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

(E)-(5S,6R)-3-benzylidene-4-(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

(E)-(5S,6R)-4-(tert-butoxycarbonyl)-5,6-diphenyl-3-ethylidene-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

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