benzyl (3S,5S,6R)-3-[(3R)-4-azido-3-(tert-butyldimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate

Base Information

Chemical Name:benzyl (3S,5S,6R)-3-[(3R)-4-azido-3-(tert-butyldimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
CAS No.:819849-55-3
Molecular Formula:C₃₄H₄₂N₄O₅Si
Molecular Weight:614.817
Hs Code.:

Synonyms:benzyl (3S,5S,6R)-3-[(3R)-4-azido-3-(tert-butyldimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate

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Chemical Property of benzyl (3S,5S,6R)-3-[(3R)-4-azido-3-(tert-butyldimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate

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Technology Process of benzyl (3S,5S,6R)-3-[(3R)-4-azido-3-(tert-butyldimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate

There total 4 articles about benzyl (3S,5S,6R)-3-[(3R)-4-azido-3-(tert-butyldimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate 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: 94.0%

: 819849-54-2
[(1R)-1-azidomethyl-3-iodopropyl]oxy-tert-butyldimethylsilane

: 100516-54-9,335159-14-3
(5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

: 819849-55-3
benzyl (3S,5S,6R)-3-[(3R)-4-azido-3-(tert-butyldimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate

Guidance literature:: With 15-crown-5; sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - -20 ℃; for 4.5h;
DOI:10.1021/jo049136w

Reference yield:

: 1025932-19-7
(R)-4-azido-3-((tert-butyl dimethylsilyl)oxy)butan-1-ol

: 819849-55-3
benzyl (3S,5S,6R)-3-[(3R)-4-azido-3-(tert-butyldimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N; DMAP / CH₂Cl₂ / 0.17 h / 0 °C

2: 1.11 g / NaI / acetone / 1 h / Heating

3: 94 percent / NaHMDS; 15-crown-5 / tetrahydrofuran / 4.5 h / -78 - -20 °C

With dmap; 15-crown-5; sodium hexamethyldisilazane; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1021/jo049136w

Reference yield:

: 1028254-61-6
(R)-4-azido-3-((tert-butyl dimethylsilyl)oxy)butyl methanesulfonate

: 819849-55-3
benzyl (3S,5S,6R)-3-[(3R)-4-azido-3-(tert-butyldimethylsilyloxy)butyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 1.11 g / NaI / acetone / 1 h / Heating

2: 94 percent / NaHMDS; 15-crown-5 / tetrahydrofuran / 4.5 h / -78 - -20 °C

With 15-crown-5; sodium hexamethyldisilazane; sodium iodide; In tetrahydrofuran; acetone;
DOI:10.1021/jo049136w