(2S,3R)-3-tert-butyldimethylsilyloxymethyl-2-((6R,2E)-7-tert-butyldiphenylsilyloxy-6-methyl-4-methylene-2-hepten-2-yl)-2-methyloxirane

Base Information

Chemical Name:(2S,3R)-3-tert-butyldimethylsilyloxymethyl-2-((6R,2E)-7-tert-butyldiphenylsilyloxy-6-methyl-4-methylene-2-hepten-2-yl)-2-methyloxirane
CAS No.:1330680-49-3
Molecular Formula:C₃₅H₅₄O₃Si₂
Molecular Weight:578.983
Hs Code.:

Synonyms:(2S,3R)-3-tert-butyldimethylsilyloxymethyl-2-((6R,2E)-7-tert-butyldiphenylsilyloxy-6-methyl-4-methylene-2-hepten-2-yl)-2-methyloxirane

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Chemical Property of (2S,3R)-3-tert-butyldimethylsilyloxymethyl-2-((6R,2E)-7-tert-butyldiphenylsilyloxy-6-methyl-4-methylene-2-hepten-2-yl)-2-methyloxirane

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Technology Process of (2S,3R)-3-tert-butyldimethylsilyloxymethyl-2-((6R,2E)-7-tert-butyldiphenylsilyloxy-6-methyl-4-methylene-2-hepten-2-yl)-2-methyloxirane

There total 6 articles about (2S,3R)-3-tert-butyldimethylsilyloxymethyl-2-((6R,2E)-7-tert-butyldiphenylsilyloxy-6-methyl-4-methylene-2-hepten-2-yl)-2-methyloxirane 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: 72.0%

: 1330680-64-2
(1E,3S,4R)-5-tert-butyldimethylsiloxy-3,4-epoxy-1-iodo-2,3-dimethyl-1-pentene

: 1330680-68-6
(R)-2-bromo-5-(tert-butyldiphenylsilyloxy)-4-methyl-1-pentene

: 1330680-49-3
(2S,3R)-3-tert-butyldimethylsilyloxymethyl-2-((6R,2E)-7-tert-butyldiphenylsilyloxy-6-methyl-4-methylene-2-hepten-2-yl)-2-methyloxirane

Guidance literature:: (R)-2-bromo-5-(tert-butyldiphenylsilyloxy)-4-methyl-1-pentene; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - 0 ℃; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; pentane; at 0 ℃; for 0.333333h; Inert atmosphere;

(1E,3S,4R)-5-tert-butyldimethylsiloxy-3,4-epoxy-1-iodo-2,3-dimethyl-1-pentene; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pentane; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol2020187

Reference yield:

: 1330680-67-5
(4S)-4-benzyl-3-[(2R)-4-bromo-2-methyl-4-pentenoyl]-1,3-oxazolidin-2-one

: 1330680-49-3
(2S,3R)-3-tert-butyldimethylsilyloxymethyl-2-((6R,2E)-7-tert-butyldiphenylsilyloxy-6-methyl-4-methylene-2-hepten-2-yl)-2-methyloxirane

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / 20 °C / pH 7 / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / Inert atmosphere

3.1: tert.-butyl lithium / tetrahydrofuran; pentane / -78 - 0 °C / Inert atmosphere

3.2: 0.33 h / 0 °C / Inert atmosphere

3.3: 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; tert.-butyl lithium; In tetrahydrofuran; dichloromethane; pentane; 3.3: Negishi coupling reaction;
DOI:10.1021/ol2020187

Reference yield:

: 1330680-57-3
(2Z,4E)-3,4-dimethyl-5-(triisopropylsilyl)-2,4-pentadien-1-ol

: 1330680-49-3
(2S,3R)-3-tert-butyldimethylsilyloxymethyl-2-((6R,2E)-7-tert-butyldiphenylsilyloxy-6-methyl-4-methylene-2-hepten-2-yl)-2-methyloxirane

Guidance literature:: Multi-step reaction with 4 steps

1.1: titanium(IV) isopropylate; di-tert-butyl peroxide; D-(-)-diisopropyl tartrate / dichloromethane / -20 - 0 °C / Inert atmosphere; Molecular sieve

2.1: 1H-imidazole / dichloromethane / Inert atmosphere

3.1: [bis(pyridine)iodine]⁺ tetrafluoroborate / 1,1,1,3',3',3'-hexafluoro-propanol / 0 - 20 °C / Inert atmosphere; Darkness

4.1: tert.-butyl lithium / tetrahydrofuran; pentane / -78 - 0 °C / Inert atmosphere

4.2: 0.33 h / 0 °C / Inert atmosphere

4.3: 0 - 20 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; di-tert-butyl peroxide; tert.-butyl lithium; [bis(pyridine)iodine]⁺ tetrafluoroborate; D-(-)-diisopropyl tartrate; In tetrahydrofuran; dichloromethane; 1,1,1,3',3',3'-hexafluoro-propanol; pentane; 4.3: Negishi coupling reaction;
DOI:10.1021/ol2020187