1-[(1R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-cyclohexyl]-propan-1-one

Base Information

Chemical Name:1-[(1R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-cyclohexyl]-propan-1-one
CAS No.:176656-02-3
Molecular Formula:C₂₅H₃₄O₃Si
Molecular Weight:410.629
Hs Code.:

Synonyms:1-[(1R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-cyclohexyl]-propan-1-one

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Chemical Property of 1-[(1R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-cyclohexyl]-propan-1-one

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Technology Process of 1-[(1R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-cyclohexyl]-propan-1-one

There total 1 articles about 1-[(1R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-cyclohexyl]-propan-1-one 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:

: 74-96-4
ethyl bromide

: 143347-68-6
(1R,4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-oxa-bicyclo[3.2.1]octan-7-one

: 176656-02-3
1-[(1R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-cyclohexyl]-propan-1-one

Guidance literature:: With magnesium; triethylamine; Yield given. Multistep reaction; 1) toluene, 25 deg C, 2) temperature below 5 deg C;
DOI:10.1021/jo951646q

Reference yield: 91.0%

: 176656-02-3
1-[(1R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-cyclohexyl]-propan-1-one

: 333-27-7
methyl trifluoromethanesulfonate

: 176656-03-4
1-[(1R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-propan-1-one

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at 25 ℃; for 48h;
DOI:10.1021/jo951646q

Reference yield:

: 176656-02-3
1-[(1R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-cyclohexyl]-propan-1-one

: (4S,6R)-4-[(E)-(1S,2S)-2-Hydroxy-4-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1,3-dimethyl-but-3-enyl]-2,2-dimethyl-1,3,7-trioxa-spiro[5.5]undec-10-en-9-one

Guidance literature:: Multi-step reaction with 13 steps

1: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 48 h / 25 °C

2: 78 percent / 1) KHMDS, HMPA / tetrahydrofuran / 1) -10 deg C -> 0 deg C, 1 h, 2) -78 deg C -> 25 deg C; 25 deg C, 12 h

3: 98 percent / K₂CO₃ / tetrahydrofuran / 12 h

6: 2,6-lutidine / CH₂Cl₂ / 12 h / 0 °C

7: NMO, OsO₄ / tetrahydrofuran / 1) 0 deg C -> 15 deg C, 10 h, 2) 25 deg C, 17 h

8: 93 percent / pyridine, DMAP / 0.5 h

9: 1) MsCl, DMAP, pyridine, 2) NaOMe / 1) 0 deg C, 3 h, 2) MeOH, 0 deg C, 1 h

10: 1) n-BuLi, 2) BF₃*Et₂O / 1) THF, -78 deg C, 15 min; -20 deg C, 15 min, 2) THF, -78 deg C, 30 min; -20 deg C, 12 h

11: 0.100 g / CSA / tetrahydrofuran; H₂O / 0.08 h

12: 1) m-CPBA, 2) p-TsOH*H₂O / 1) CH₂Cl₂, 0 deg C, 1.5 h, 2) CH₂Cl₂, 1 h

13: 54 percent / HF/pyridine reagent / pyridine / 12 h / 25 °C

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; pyridine reagent; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; sodium methylate; potassium hexamethylsilazane; potassium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; pyridine; dichloromethane; water;
DOI:10.1021/jo951646q