(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-[3-(tert-butyldimethylsilyloxy)propyl]cyclohexanone

Base Information

Chemical Name:(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-[3-(tert-butyldimethylsilyloxy)propyl]cyclohexanone
CAS No.:608535-12-2
Molecular Formula:C₂₇H₅₈O₄Si₃
Molecular Weight:531.012
Hs Code.:

Synonyms:(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-[3-(tert-butyldimethylsilyloxy)propyl]cyclohexanone

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Chemical Property of (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-[3-(tert-butyldimethylsilyloxy)propyl]cyclohexanone

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Technology Process of (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-[3-(tert-butyldimethylsilyloxy)propyl]cyclohexanone

There total 7 articles about (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-[3-(tert-butyldimethylsilyloxy)propyl]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: 100.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 608535-11-1
(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-(3-hydroxypropyl)cyclohexanone

: 608535-12-2
(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-[3-(tert-butyldimethylsilyloxy)propyl]cyclohexanone

Guidance literature:: With dmap; triethylamine;
DOI:10.1055/s-2003-39908

Reference yield:

: 139356-32-4
methyl (1s_n,3R,4s_n,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-[(imidazol-1-ylthiocarbonyl)oxy]-cyclohexanecarboxylate

: 608535-12-2
(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-[3-(tert-butyldimethylsilyloxy)propyl]cyclohexanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 60 percent / AIBN / benzene / 3 h / Heating

2.1: BH₃*THF / tetrahydrofuran / 2 h / 20 °C

2.2: NaOH; H₂O₂ / tetrahydrofuran; H₂O / 2 h / 20 °C

3.1: NaBH₄ / ethanol / 2 h / 20 °C

4.1: 31 mg / NaIO₄ / methanol; H₂O / 14 h / 20 °C

5.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

With dmap; sodium tetrahydroborate; sodium periodate; borane-THF; 2,2'-azobis(isobutyronitrile); triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; benzene;
DOI:10.1021/jo034787y

Reference yield:

: methyl (3R,5R)-4-allyl-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-hydroxycyclohexanecarboxylate

: 608535-12-2
(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-[3-(tert-butyldimethylsilyloxy)propyl]cyclohexanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: BH₃*THF / tetrahydrofuran / 2 h / 20 °C

1.2: NaOH; H₂O₂ / tetrahydrofuran; H₂O / 2 h / 20 °C

2.1: NaBH₄ / ethanol / 2 h / 20 °C

3.1: 31 mg / NaIO₄ / methanol; H₂O / 14 h / 20 °C

4.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

With dmap; sodium tetrahydroborate; sodium periodate; borane-THF; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;
DOI:10.1021/jo034787y