(2R,3R,5R)-2,3-bis-(O-trimethylsilyl)-2,3-dihydroxy-5-(1',3'-E,E-1'-heptadienyl)-cyclohexanone

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Chemical Name:(2R,3R,5R)-2,3-bis-(O-trimethylsilyl)-2,3-dihydroxy-5-(1',3'-E,E-1'-heptadienyl)-cyclohexanone
CAS No.:128856-71-3
Molecular Formula:C₁₉H₃₆O₃Si₂
Molecular Weight:368.664
Hs Code.:

Synonyms:(2R,3R,5R)-2,3-bis-(O-trimethylsilyl)-2,3-dihydroxy-5-(1',3'-E,E-1'-heptadienyl)-cyclohexanone

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Chemical Property of (2R,3R,5R)-2,3-bis-(O-trimethylsilyl)-2,3-dihydroxy-5-(1',3'-E,E-1'-heptadienyl)-cyclohexanone

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Technology Process of (2R,3R,5R)-2,3-bis-(O-trimethylsilyl)-2,3-dihydroxy-5-(1',3'-E,E-1'-heptadienyl)-cyclohexanone

There total 8 articles about (2R,3R,5R)-2,3-bis-(O-trimethylsilyl)-2,3-dihydroxy-5-(1',3'-E,E-1'-heptadienyl)-cyclohexanone 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: 92.0%

: 75-77-4
chloro-trimethyl-silane

: 128856-70-2
(2R,3R,5R)-5-((1E,3E)-hepta-1,3-dienyl)-2,3-dihydroxycyclohexanone

: 128856-71-3
(2R,3R,5R)-2,3-bis-(O-trimethylsilyl)-2,3-dihydroxy-5-(1',3'-E,E-1'-heptadienyl)-cyclohexanone

Guidance literature:: With 1H-imidazole; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1016/S0040-4020(01)89132-8

Reference yield: 80.0%

: 764-58-9
(E)-hept-3-ene-1-yne

: 251959-52-1
(5R,6R)-bis-trimethylsiloxy-2-cyclohexenone

: 128856-71-3
(2R,3R,5R)-2,3-bis-(O-trimethylsilyl)-2,3-dihydroxy-5-(1',3'-E,E-1'-heptadienyl)-cyclohexanone

Guidance literature:: (E)-hept-3-ene-1-yne; (5R,6R)-bis-trimethylsiloxy-2-cyclohexenone; With Schwartz's reagent; (lithium)2(CN)(methyl)2cuprate; In tetrahydrofuran; at -78 ℃; for 0.666667h;

With water; ammonium chloride;
DOI:10.1016/S0040-4039(99)01549-X

Reference yield:

: 225793-33-9
(5R)-5-(tert-butyldimethylsiloxy)cyclohex-2-enone

: 128856-71-3
(2R,3R,5R)-2,3-bis-(O-trimethylsilyl)-2,3-dihydroxy-5-(1',3'-E,E-1'-heptadienyl)-cyclohexanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / H₂O; OsO₄; N-methylmorpholine N-oxide / acetone / 24 h / 20 °C

2.1: 97 percent / acetonitrile / 15 h / 20 °C

3.1: 100 percent

4.1: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / -30 °C

5.1: Cp₂Zr(H)Cl; Me₂Cu(CN)Li₂ / tetrahydrofuran / 0.67 h / -78 °C

5.2: 80 percent / NH₄Cl; H₂O

With osmium(VIII) oxide; Schwartz's reagent; tetrabutyl ammonium fluoride; water; (lithium)2(CN)(methyl)2cuprate; 4-methylmorpholine N-oxide; In tetrahydrofuran; acetone; acetonitrile; 1.1: Oxidation / 2.1: silylation / 3.1: silylation / 4.1: Elimination / 5.1: Addition / 5.2: Hydrolysis;
DOI:10.1016/S0040-4039(99)01549-X