(2'S,3'S,4S)-(E)-2,2-dimethyl-3-N-(tert-butoxycarbonyl)-4-[3'-(1'-(benzyloxy)-2',3'-epoxypropyl)]oxazolidine

Base Information

Chemical Name:(2'S,3'S,4S)-(E)-2,2-dimethyl-3-N-(tert-butoxycarbonyl)-4-[3'-(1'-(benzyloxy)-2',3'-epoxypropyl)]oxazolidine
CAS No.:198274-39-4
Molecular Formula:C₂₀H₂₉NO₅
Molecular Weight:363.454
Hs Code.:

Synonyms:(2'S,3'S,4S)-(E)-2,2-dimethyl-3-N-(tert-butoxycarbonyl)-4-[3'-(1'-(benzyloxy)-2',3'-epoxypropyl)]oxazolidine

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Chemical Property of (2'S,3'S,4S)-(E)-2,2-dimethyl-3-N-(tert-butoxycarbonyl)-4-[3'-(1'-(benzyloxy)-2',3'-epoxypropyl)]oxazolidine

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Technology Process of (2'S,3'S,4S)-(E)-2,2-dimethyl-3-N-(tert-butoxycarbonyl)-4-[3'-(1'-(benzyloxy)-2',3'-epoxypropyl)]oxazolidine

There total 3 articles about (2'S,3'S,4S)-(E)-2,2-dimethyl-3-N-(tert-butoxycarbonyl)-4-[3'-(1'-(benzyloxy)-2',3'-epoxypropyl)]oxazolidine 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: 70.0%

: 100-39-0
benzyl bromide

: 198274-38-3
(2'S,3'S,4S)-(-)-(E)-2,2-dimethyl-3-N-(tert-butoxycarbonyl)-4-[3'-(1'-hydroxy-1',2'-epoxypropyl)]oxazolidine

: 198274-39-4
(2'S,3'S,4S)-(E)-2,2-dimethyl-3-N-(tert-butoxycarbonyl)-4-[3'-(1'-(benzyloxy)-2',3'-epoxypropyl)]oxazolidine

Guidance literature:: (2'S,3'S,4S)-(-)-(E)-2,2-dimethyl-3-N-(tert-butoxycarbonyl)-4-[3'-(1'-hydroxy-1',2'-epoxypropyl)]oxazolidine; With sodium hydride; In tetrahydrofuran; at 0 - 25 ℃; for 1h;

benzyl bromide; In tetrahydrofuran; at 0 - 25 ℃;
DOI:10.1021/jo9708607

Reference yield:

: 102308-32-7
(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 198274-39-4
(2'S,3'S,4S)-(E)-2,2-dimethyl-3-N-(tert-butoxycarbonyl)-4-[3'-(1'-(benzyloxy)-2',3'-epoxypropyl)]oxazolidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 61 percent / butyllithium; diisopropylamine / tetrahydrofuran / 3 h / -78 - 25 °C

2.1: 54 percent / NaBH₄ / tetrahydrofuran; H₂O / 12 h / 0 - 25 °C

3.1: NaH / tetrahydrofuran / 1 h / 0 - 25 °C

3.2: 70 percent / tetrahydrofuran / 0 - 25 °C

With sodium tetrahydroborate; n-butyllithium; sodium hydride; diisopropylamine; In tetrahydrofuran; water; 1.1: Condensation / 2.1: Reduction / 3.1: Metallation / 3.2: Etherification;
DOI:10.1021/jo9708607

Reference yield:

: 198274-37-2
(1'R,2'S,4S)-(E)-2,2-dimethyl-3-N-(tert-butoxycarbonyl)-4-[3'-(1'-carbethoxy-1',2'-epoxyethyl)]oxazolidine

: 198274-39-4
(2'S,3'S,4S)-(E)-2,2-dimethyl-3-N-(tert-butoxycarbonyl)-4-[3'-(1'-(benzyloxy)-2',3'-epoxypropyl)]oxazolidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 54 percent / NaBH₄ / tetrahydrofuran; H₂O / 12 h / 0 - 25 °C

2.1: NaH / tetrahydrofuran / 1 h / 0 - 25 °C

2.2: 70 percent / tetrahydrofuran / 0 - 25 °C

With sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; water; 1.1: Reduction / 2.1: Metallation / 2.2: Etherification;
DOI:10.1021/jo9708607