(+)-(2R,3R,5R)-2-hydroxymethyl-3-(1,3-heptadienyl)-5-(tert-butyldimethylsiloxy)cyclohexanone

Base Information

Chemical Name:(+)-(2R,3R,5R)-2-hydroxymethyl-3-(1,3-heptadienyl)-5-(tert-butyldimethylsiloxy)cyclohexanone
CAS No.:224967-47-9
Molecular Formula:C₂₀H₃₆O₃Si
Molecular Weight:352.59
Hs Code.:

Synonyms:(+)-(2R,3R,5R)-2-hydroxymethyl-3-(1,3-heptadienyl)-5-(tert-butyldimethylsiloxy)cyclohexanone

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Chemical Property of (+)-(2R,3R,5R)-2-hydroxymethyl-3-(1,3-heptadienyl)-5-(tert-butyldimethylsiloxy)cyclohexanone

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Technology Process of (+)-(2R,3R,5R)-2-hydroxymethyl-3-(1,3-heptadienyl)-5-(tert-butyldimethylsiloxy)cyclohexanone

There total 5 articles about (+)-(2R,3R,5R)-2-hydroxymethyl-3-(1,3-heptadienyl)-5-(tert-butyldimethylsiloxy)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:

: 130158-22-4
ethyl (S)-3-((tert-butyldimethylsilyl)oxy)-4-iodobutanoate

: 224967-47-9
(+)-(2R,3R,5R)-2-hydroxymethyl-3-(1,3-heptadienyl)-5-(tert-butyldimethylsiloxy)cyclohexanone

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) CuI, 2.) N,N'-(dimethylpropylene)urea, (EtO)3P / 1.) THF, -35 deg C, 15 min, 2.) THF, from -35 deg C to RT

2: Ti(Oi-Pr)4, i-PrMgCl / diethyl ether / a) -45 to -40 deg C, 1 h, b) from -40 deg C to RT, 90 min, c) RT, 2 h

3: FeCl₃, pyridine / dimethylformamide / 0.5 h / Ambient temperature

4: NaOAc / methanol / 1 h / Ambient temperature

5: 1.) Cp₂Zr(H)Cl, 3.) LiCl, CuCN

With pyridine; titanium(IV) isopropylate; copper(l) iodide; Schwartz's reagent; 4,4,5-trimethyl-2-imidazolidinone; isopropylmagnesium chloride; sodium acetate; iron(III) chloride; lithium chloride; triethyl phosphite; In methanol; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ja9843122

Reference yield:

: (1RS,3R)-1-hydroxy-3-(tert-butyldimethylsiloxy)bicyclo<3.1.0>hexane

: 224967-47-9
(+)-(2R,3R,5R)-2-hydroxymethyl-3-(1,3-heptadienyl)-5-(tert-butyldimethylsiloxy)cyclohexanone

Guidance literature:: Multi-step reaction with 3 steps

1: FeCl₃, pyridine / dimethylformamide / 0.5 h / Ambient temperature

2: NaOAc / methanol / 1 h / Ambient temperature

3: 1.) Cp₂Zr(H)Cl, 3.) LiCl, CuCN

With pyridine; Schwartz's reagent; sodium acetate; iron(III) chloride; lithium chloride; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja9843122

Reference yield:

: 3-(tert-butyl-dimethyl-silanyloxy)-5-chloro-cyclohexanone

: 224967-47-9
(+)-(2R,3R,5R)-2-hydroxymethyl-3-(1,3-heptadienyl)-5-(tert-butyldimethylsiloxy)cyclohexanone

Guidance literature:: Multi-step reaction with 2 steps

1: NaOAc / methanol / 1 h / Ambient temperature

2: 1.) Cp₂Zr(H)Cl, 3.) LiCl, CuCN

With Schwartz's reagent; sodium acetate; lithium chloride; In methanol;
DOI:10.1021/ja9843122