(3R,4R)-4-tert-butyldimethylsiloxy-3-(2-propenyl)cyclohexanone

Base Information

Chemical Name:(3R,4R)-4-tert-butyldimethylsiloxy-3-(2-propenyl)cyclohexanone
CAS No.:181230-63-7
Molecular Formula:C₁₅H₂₈O₂Si
Molecular Weight:268.472
Hs Code.:

Synonyms:(3R,4R)-4-tert-butyldimethylsiloxy-3-(2-propenyl)cyclohexanone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4R)-4-tert-butyldimethylsiloxy-3-(2-propenyl)cyclohexanone

Chemical Property:

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Technology Process of (3R,4R)-4-tert-butyldimethylsiloxy-3-(2-propenyl)cyclohexanone

There total 1 articles about (3R,4R)-4-tert-butyldimethylsiloxy-3-(2-propenyl)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: 71.0%

: 157035-24-0
(4S,5R)-5-allyl-4-(tert-butyldimethylsiloxy)cyclohex-2-enone

: 181230-63-7
(3R,4R)-4-tert-butyldimethylsiloxy-3-(2-propenyl)cyclohexanone

Guidance literature:: With sodium dithionite; adogen 464; sodium hydrogencarbonate; In water; benzene; Heating;
DOI:10.1016/00404-0399(50)1044I-

Reference yield: 89.0%

: 1530-32-1
ethyltriphenylphosphonium bromide

: 181230-63-7
(3R,4R)-4-tert-butyldimethylsiloxy-3-(2-propenyl)cyclohexanone

: (1R,2R)-4-tert-butyldimethylsiloxy-4-ethylidene-2-(2-propenyl)cyclohexane

Guidance literature:: With n-butyllithium; In tetrahydrofuran; Heating;
DOI:10.1016/00404-0399(50)1044I-

Reference yield:

: 181230-63-7
(3R,4R)-4-tert-butyldimethylsiloxy-3-(2-propenyl)cyclohexanone

: 181230-67-1
(8S,9S,12S)-4,5-didehydro-4-phenylthiomethyl-17,18,19-trisnoraphidicolin-3,16-dione 16,16-ethylene acetal

Guidance literature:: Multi-step reaction with 17 steps

1: 1.) n-BuLi / 1.) THF, hexane, reflux, 1.5 h, 2.) THF, hexane, 2 h

2: 83 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 12 h / Ambient temperature

3: 91 percent / 4A-MS, NMO, n-Pr₄N⁽¹⁺⁾*RuO₄^(1-) / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) RT, 1 h

4: 100 percent / PPTS / benzene / 2.5 h / Heating

5: 93 percent / O₂, PdCl₂, CuCl / dimethylformamide; H₂O / 5 h / 45 °C

6: 1.) LDA / 1.) THF, hexane, -78 deg C, 50 min, 2.) THF, hexane, a) -78 deg C, 80 min, b) 0 deg C, 10 min

7: 86 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 45 min, 2.) 0 deg C, 0.5 h

8: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, -78 deg C, 1 h

9: 76 percent / P(o-tolyl)3, (dba)3Pd₂*CHCl₃, AcOH / benzene / 15 h / 60 °C / var. reagents and solvents; var. temp. and reaction time

10: 69 percent / PdCl₂, CuCl, O₂ / dimethylformamide; H₂O / 11 h / 60 °C

11: 96 percent / H₂ / 10percent Pd-C / ethanol / 5 h / Ambient temperature

12: 1.) n-BuLi / 1.) DME, hexane, reflux, 2.5 h, 2.) DME, hexane, RT, 7 h

13: 78 percent / NMO, 4A-MS, n-Pr₄N⁽¹⁺⁾*RuO₄^(1-) / CH₂Cl₂ / 1 h / Ambient temperature

14: 1.) n-BuLi, HPMA / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, hexane, a) -78 deg C, 10 min, b) 0 deg C, 0.5 h, c) RT, 2 h

15: 70 percent / methylene blue / toluene / 190 h / 220 °C

16: 1.) hematoporphiryn, O₂, pyridine, 2.) NaI, 3.) NMO, 4A-MS, n-Pr₄N⁽¹⁺⁾*RuO₄^(1-)

17: 95 percent / Et₃N / ethanol / 48 h / Heating

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 13,17-bis(2-carboxylatoethyl)-3,8-bis[1-hydroxyethyl]-2,7,12,18-tetramethylporphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; oxygen; methylene blue; pyridinium p-toluenesulfonate; acetic acid; triethylamine; tris-(o-tolyl)phosphine; sodium iodide; copper(l) chloride; palladium dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/0040-4020(96)00575-3