(3R,4R,5R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-hydroxy-4-methoxy-3,4,5,6-tetrahydro-2H-1,2-oxazine

Base Information

Chemical Name:(3R,4R,5R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-hydroxy-4-methoxy-3,4,5,6-tetrahydro-2H-1,2-oxazine
CAS No.:857856-14-5
Molecular Formula:C₁₇H₂₅NO₅
Molecular Weight:323.389
Hs Code.:

Synonyms:(3R,4R,5R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-hydroxy-4-methoxy-3,4,5,6-tetrahydro-2H-1,2-oxazine

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Chemical Property of (3R,4R,5R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-hydroxy-4-methoxy-3,4,5,6-tetrahydro-2H-1,2-oxazine

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Technology Process of (3R,4R,5R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-hydroxy-4-methoxy-3,4,5,6-tetrahydro-2H-1,2-oxazine

There total 3 articles about (3R,4R,5R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-hydroxy-4-methoxy-3,4,5,6-tetrahydro-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: 80.0%

: 227622-58-4
(3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine

: 857856-14-5
(3R,4R,5R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-hydroxy-4-methoxy-3,4,5,6-tetrahydro-2H-1,2-oxazine

Guidance literature:: (3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine; With borane-THF; In tetrahydrofuran; at -30 - 20 ℃;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at -10 - 20 ℃; Further stages.;
DOI:10.1021/ol0260573

Reference yield: 19.0%

: 227622-58-4
(3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine

: 1312677-93-2
(3S,4S,5S,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-hydroxy-4-methoxy-3,4,5,6-tetrahydro-2H-1,2-oxazine

: 857856-14-5
(3R,4R,5R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-hydroxy-4-methoxy-3,4,5,6-tetrahydro-2H-1,2-oxazine

Guidance literature:: (3S,4′S)-2-benzyl-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine; With borane-THF; In tetrahydrofuran; at -30 - 20 ℃; Inert atmosphere;

With water; dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; at -10 - 20 ℃; stereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201100230

Reference yield:

: 91190-38-4,111058-38-9,1165677-00-8
N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone

: 857856-14-5
(3R,4R,5R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-hydroxy-4-methoxy-3,4,5,6-tetrahydro-2H-1,2-oxazine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 81 percent / tetrahydrofuran / 1 h / -78 °C

2.1: BH₃*THF / tetrahydrofuran / -30 - 20 °C

2.2: 80 percent / aq. H₂O₂; NaOH / tetrahydrofuran / -10 - 20 °C

With borane-THF; In tetrahydrofuran;
DOI:10.1021/ol0260573