[2R,2(1E,3S),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-3-methyl-but-1-enyl)-4-phenyl-1,3-oxazolidine

Base Information

Chemical Name:[2R,2(1E,3S),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-3-methyl-but-1-enyl)-4-phenyl-1,3-oxazolidine
CAS No.:234123-02-5
Molecular Formula:C₂₆H₃₃NO₄
Molecular Weight:423.552
Hs Code.:

Synonyms:[2R,2(1E,3S),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-3-methyl-but-1-enyl)-4-phenyl-1,3-oxazolidine

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Chemical Property of [2R,2(1E,3S),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-3-methyl-but-1-enyl)-4-phenyl-1,3-oxazolidine

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Technology Process of [2R,2(1E,3S),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-3-methyl-but-1-enyl)-4-phenyl-1,3-oxazolidine

There total 8 articles about [2R,2(1E,3S),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-3-methyl-but-1-enyl)-4-phenyl-1,3-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: 78.0%

: 234122-96-4
[2R,2(1S,2E),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-1-methanesulfonyloxy-but-2-enyl)-4-phenyl-1,3-oxazolidine

: 234123-02-5
[2R,2(1E,3S),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-3-methyl-but-1-enyl)-4-phenyl-1,3-oxazolidine

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1016/S0040-4039(99)00800-X

Reference yield:

: 917-54-4
methyllithium

: 234122-96-4
[2R,2(1S,2E),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-1-methanesulfonyloxy-but-2-enyl)-4-phenyl-1,3-oxazolidine

: 234123-02-5
[2R,2(1E,3S),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-3-methyl-but-1-enyl)-4-phenyl-1,3-oxazolidine

Guidance literature:: methyllithium; With copper(l) iodide; In tetrahydrofuran; diethyl ether; at -78 - -20 ℃;

[2R,2(1S,2E),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-1-methanesulfonyloxy-but-2-enyl)-4-phenyl-1,3-oxazolidine; In tetrahydrofuran; diethyl ether; at -60 ℃; for 1h;
DOI:10.1016/S0040-4020(99)00949-7

Reference yield:

: 164530-43-2
Weinreb amide

: 234123-02-5
[2R,2(1E,3S),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-3-methyl-but-1-enyl)-4-phenyl-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 75 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - -10 °C

2.1: 94 percent / Zn(BH₄)2 / diethyl ether / 1 h / 0 °C

3.1: 80 percent / Red-Al / toluene; tetrahydrofuran / 0.5 h / 20 °C

4.1: Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

5.1: copper iodide / tetrahydrofuran; diethyl ether / -78 - -20 °C

5.2: tetrahydrofuran; diethyl ether / 1 h / -60 °C

With copper(l) iodide; n-butyllithium; zinc(II) tetrahydroborate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 1.1: Substitution / 2.1: Reduction / 3.1: Reduction / 4.1: mesylation / 5.1: Addition / 5.2: Methylation;
DOI:10.1016/S0040-4020(99)00949-7