tert-butyl (3S,5S,6R)-3-[(3R)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate

Base Information

Chemical Name:tert-butyl (3S,5S,6R)-3-[(3R)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate
CAS No.:753010-18-3
Molecular Formula:C₂₅H₃₀INO₅
Molecular Weight:551.421
Hs Code.:

Synonyms:tert-butyl (3S,5S,6R)-3-[(3R)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate

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Chemical Property of tert-butyl (3S,5S,6R)-3-[(3R)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate

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Technology Process of tert-butyl (3S,5S,6R)-3-[(3R)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate

There total 3 articles about tert-butyl (3S,5S,6R)-3-[(3R)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-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: 47.0%

: 937183-38-5
tert-butyl (3S,5S,6R)-3-(2-((RS)oxiran-2-yl)ethyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate

: 753010-19-4
tert-butyl (3S,5S,6R)-3-[(3S)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate

: 753010-18-3
tert-butyl (3S,5S,6R)-3-[(3R)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate

Guidance literature:: With acetic acid; sodium iodide; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1016/j.tetasy.2004.06.004

Reference yield:

: 112741-49-8,173397-90-5
tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate

: 753010-18-3
tert-butyl (3S,5S,6R)-3-[(3R)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 60 percent / HMPA; (Me₃Si)2NLi / tetrahydrofuran; CH₂Cl₂ / 4 h / -78 - -40 °C

2: 88.7 percent / mCPBA; phosphate buffer / 1,2-dichloro-ethane / 12 h / 20 °C / pH 7

3: 47 percent / AcOH; NaI / tetrahydrofuran / 1 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; phosphate buffer; acetic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1016/j.tetasy.2004.06.004

Reference yield:

: 144542-72-3
(3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

: 753010-18-3
tert-butyl (3S,5S,6R)-3-[(3R)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 88.7 percent / mCPBA; phosphate buffer / 1,2-dichloro-ethane / 12 h / 20 °C / pH 7

2: 47 percent / AcOH; NaI / tetrahydrofuran / 1 h / 20 °C

With phosphate buffer; acetic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; 1,2-dichloro-ethane;
DOI:10.1016/j.tetasy.2004.06.004