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

Base Information

Chemical Name:[2R,2(1S,2E),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-1-methanesulfonyloxy-but-2-enyl)-4-phenyl-1,3-oxazolidine
CAS No.:234122-97-5
Molecular Formula:C₂₅H₄₁NO₇SSi
Molecular Weight:527.755
Hs Code.:

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

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

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

There total 6 articles about [2R,2(1S,2E),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-1-methanesulfonyloxy-but-2-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: 98.0%

: 124-63-0
methanesulfonyl chloride

: 234122-95-3
[2R,2(1S,2E),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-1-hydroxy-but-2-enyl)-4-phenyl-1,3-oxazolidine

: 234122-97-5
[2R,2(1S,2E),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-1-methanesulfonyloxy-but-2-enyl)-4-phenyl-1,3-oxazolidine

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1016/S0040-4020(99)00949-7

Reference yield:

: 164530-43-2
Weinreb amide

: 234122-97-5
[2R,2(1S,2E),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-1-methanesulfonyloxy-but-2-enyl)-4-phenyl-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 77 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - -10 °C

2: 95 percent / Zn(BH₄)2 / diethyl ether / 1 h / 0 °C

3: 85 percent / Red-Al / toluene; tetrahydrofuran / 0.5 h / 20 °C

4: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

With n-butyllithium; zinc(II) tetrahydroborate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 1: Substitution / 2: Reduction / 3: Reduction / 4: mesylation;
DOI:10.1016/S0040-4020(99)00949-7

Reference yield:

: 179600-33-0
[2R,2(1S),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-1-hydroxy-but-2-ynyl)-4-phenyl-1,3-oxazolidine

: 234122-97-5
[2R,2(1S,2E),4R]-3-tert-butoxycarbonyl-2-(4-tert-butyldimethylsilyloxy-1-methanesulfonyloxy-but-2-enyl)-4-phenyl-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / Red-Al / toluene; tetrahydrofuran / 0.5 h / 20 °C

2: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

With triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; toluene; 1: Reduction / 2: mesylation;
DOI:10.1016/S0040-4020(99)00949-7