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

Base Information

Chemical Name:(2S,3R,8R)-2-(tert-Butyldiphenylsilyloxymethyl)-10,10-ethylenedioxy-8-methylundecane-1,3-diol
CAS No.:136155-18-5
Molecular Formula:C₃₁H₄₈O₅Si
Molecular Weight:528.805
Hs Code.:

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

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Chemical Property of (2S,3R,8R)-2-(tert-Butyldiphenylsilyloxymethyl)-10,10-ethylenedioxy-8-methylundecane-1,3-diol

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Technology Process of (2S,3R,8R)-2-(tert-Butyldiphenylsilyloxymethyl)-10,10-ethylenedioxy-8-methylundecane-1,3-diol

There total 15 articles about (2S,3R,8R)-2-(tert-Butyldiphenylsilyloxymethyl)-10,10-ethylenedioxy-8-methylundecane-1,3-diol 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: 96.0%

: 136155-16-3,136155-17-4,143289-33-2,143289-34-3
(2S,3R,5RS,8R)-2-(tert-Butyldiphenylsilyloxymethyl)-10,10-ethylenedioxy-8-methyl-5-(phenylsulfonyl)undecane-1,3-diol

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

Guidance literature:: With disodium hydrogenphosphate; sodium amalgam; In ethanol; for 1h; Ambient temperature;

Reference yield:

: 102573-92-2
2-(hydroxymethyl)-3-butyn-1-ol

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

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / pyridine / 3 h / Ambient temperature

2: 97 percent / H₂ / Lindlar / ethyl acetate / 24 h / Ambient temperature

3: 8 h / 0 °C / asymmetric hydrolysis with Lipase P, acetate buffer, pH 5

4: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C

5: 87 percent / 80percent MCPBA, NaHCO₃ / CH₂Cl₂ / 12 h / Heating

6: 38 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

7: 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

8: 96 percent / Na/Hg, dibasic sodium phosphate / ethanol / 1 h / Ambient temperature

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; ethylmagnesium bromide; hydrogen; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

: 136155-05-0
2-Acetoxymethyl-3-butynyl acetate

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

Guidance literature:: Multi-step reaction with 7 steps

1: 97 percent / H₂ / Lindlar / ethyl acetate / 24 h / Ambient temperature

2: 8 h / 0 °C / asymmetric hydrolysis with Lipase P, acetate buffer, pH 5

3: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C

4: 87 percent / 80percent MCPBA, NaHCO₃ / CH₂Cl₂ / 12 h / Heating

5: 38 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

6: 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

7: 96 percent / Na/Hg, dibasic sodium phosphate / ethanol / 1 h / Ambient temperature

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; ethylmagnesium bromide; hydrogen; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;