(4R,9R,10S)-10-(tert-Butyldiphenylsilyloxymethyl)-9,10-isopropylidenedioxy-4-methyl-2-undecanone

Base Information

Chemical Name:(4R,9R,10S)-10-(tert-Butyldiphenylsilyloxymethyl)-9,10-isopropylidenedioxy-4-methyl-2-undecanone
CAS No.:136155-19-6
Molecular Formula:C₃₂H₄₈O₄Si
Molecular Weight:524.816
Hs Code.:

Synonyms:(4R,9R,10S)-10-(tert-Butyldiphenylsilyloxymethyl)-9,10-isopropylidenedioxy-4-methyl-2-undecanone

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Chemical Property of (4R,9R,10S)-10-(tert-Butyldiphenylsilyloxymethyl)-9,10-isopropylidenedioxy-4-methyl-2-undecanone

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Technology Process of (4R,9R,10S)-10-(tert-Butyldiphenylsilyloxymethyl)-9,10-isopropylidenedioxy-4-methyl-2-undecanone

There total 5 articles about (4R,9R,10S)-10-(tert-Butyldiphenylsilyloxymethyl)-9,10-isopropylidenedioxy-4-methyl-2-undecanone 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: 95.0%

: 136155-18-5
(2S,3R,8R)-2-(tert-Butyldiphenylsilyloxymethyl)-10,10-ethylenedioxy-8-methylundecane-1,3-diol

: 77-76-9
2,2-dimethoxy-propane

: 136155-19-6
(4R,9R,10S)-10-(tert-Butyldiphenylsilyloxymethyl)-9,10-isopropylidenedioxy-4-methyl-2-undecanone

Guidance literature:: With pyridinium p-toluenesulfonate; In acetone; for 12h; Heating;

Reference yield:

: 136155-04-9
(S)-2-(tert-Butyldiphenylsilyloxymethyl)-3-butenyl acetate

: 136155-19-6
(4R,9R,10S)-10-(tert-Butyldiphenylsilyloxymethyl)-9,10-isopropylidenedioxy-4-methyl-2-undecanone

Guidance literature:: Multi-step reaction with 5 steps

1: 87 percent / 80percent MCPBA, NaHCO₃ / CH₂Cl₂ / 12 h / Heating

2: 38 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

3: 1a) EtMgBr, HMPA, 1b) 1.49 M n-BuLi, HMPA / 1a) THF, -78 deg C, 30 min, 1b) THF, n-hexane, -78 deg C, 2) -78 deg C, 1 h

4: 96 percent / Na/Hg, dibasic sodium phosphate / ethanol / 1 h / Ambient temperature

5: 95 percent / pyridinium p-toluenesulfonate / acetone / 12 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; ethylmagnesium bromide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In methanol; ethanol; dichloromethane; acetone;

Reference yield:

: 136155-06-1,136155-07-2
(2S,3RS)-2-(tert-Butyldiphenylsilyloxymethyl)-3,4-epoxybutyl acetate

: 136155-19-6
(4R,9R,10S)-10-(tert-Butyldiphenylsilyloxymethyl)-9,10-isopropylidenedioxy-4-methyl-2-undecanone

Guidance literature:: Multi-step reaction with 4 steps

1: 38 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

2: 1a) EtMgBr, HMPA, 1b) 1.49 M n-BuLi, HMPA / 1a) THF, -78 deg C, 30 min, 1b) THF, n-hexane, -78 deg C, 2) -78 deg C, 1 h

3: 96 percent / Na/Hg, dibasic sodium phosphate / ethanol / 1 h / Ambient temperature

4: 95 percent / pyridinium p-toluenesulfonate / acetone / 12 h / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; ethylmagnesium bromide; pyridinium p-toluenesulfonate; potassium carbonate; In methanol; ethanol; acetone;