(3S,4'R,5'S)-2-benzyl-3-(5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine

Base Information

Chemical Name:(3S,4'R,5'S)-2-benzyl-3-(5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine
CAS No.:1392007-32-7
Molecular Formula:C₂₄H₃₉NO₅Si
Molecular Weight:449.663
Hs Code.:

Synonyms:(3S,4'R,5'S)-2-benzyl-3-(5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine

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Chemical Property of (3S,4'R,5'S)-2-benzyl-3-(5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine

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Technology Process of (3S,4'R,5'S)-2-benzyl-3-(5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine

There total 4 articles about (3S,4'R,5'S)-2-benzyl-3-(5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]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: 84.0%

: 1392007-21-4
(3S,4'R,5'S)-2-benzyl-3-(5'-hydroxymethyl-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1392007-32-7
(3S,4'R,5'S)-2-benzyl-3-(5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201200158

Reference yield:

: 13169-00-1
Methoxyallene

: 1392007-26-9,718613-98-0
(E)-(4'R,5'S)-benzyl-[1-[5-(tert-butyl-dimethylsiloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]methylidene]amine N-oxide

: 1392007-29-2
(3R,4'R,5'S)-2-benzyl-3-(5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine

: 1392007-32-7
(3S,4'R,5'S)-2-benzyl-3-(5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine

Guidance literature:: Methoxyallene; With n-butyllithium; In tetrahydrofuran; hexane; at -40 ℃; for 0.0833333h; Inert atmosphere;

(E)-(4'R,5'S)-benzyl-[1-[5-(tert-butyl-dimethylsiloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]methylidene]amine N-oxide; In tetrahydrofuran; hexane; at -78 ℃; for 1h; optical yield given as %de; Inert atmosphere;
DOI:10.1002/ejoc.201200158

Reference yield:

: (2S,3S,4S)-N-benzyl-N-hydroxy-3,4-isopropylidenedioxytetrahydrofuran-2-amine

: 1392007-32-7
(3S,4'R,5'S)-2-benzyl-3-(5'-(tert-butyldimethylsiloxymethyl)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole; dmap / dichloromethane / 72 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -40 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/ejoc.201200158