(-)-<1S(7S,10S),4R>-<10-<(tert-butyldiphenylsilyloxy)methyl>-8-methylene-1,4-dioxaspiro<4.5>decan-7-yl> 4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>heptane-1-carboxylate

Base Information

Chemical Name:(-)-<1S(7S,10S),4R>-<10-<(tert-butyldiphenylsilyloxy)methyl>-8-methylene-1,4-dioxaspiro<4.5>decan-7-yl> 4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>heptane-1-carboxylate
CAS No.:127818-24-0
Molecular Formula:C₃₆H₄₆O₇Si
Molecular Weight:618.843
Hs Code.:

(-)-<1S(7S,10S),4R>-<10-<(tert-butyldiphenylsilyloxy)methyl>-8-methylene-1,4-dioxaspiro<4.5>decan-7-yl> 4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>heptane-1-carboxylate

Synonyms:(-)-<1S(7S,10S),4R>-<10-<(tert-butyldiphenylsilyloxy)methyl>-8-methylene-1,4-dioxaspiro<4.5>decan-7-yl> 4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>heptane-1-carboxylate

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Chemical Property of (-)-<1S(7S,10S),4R>-<10-<(tert-butyldiphenylsilyloxy)methyl>-8-methylene-1,4-dioxaspiro<4.5>decan-7-yl> 4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>heptane-1-carboxylate

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Technology Process of (-)-<1S(7S,10S),4R>-<10-<(tert-butyldiphenylsilyloxy)methyl>-8-methylene-1,4-dioxaspiro<4.5>decan-7-yl> 4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>heptane-1-carboxylate

There total 6 articles about (-)-<1S(7S,10S),4R>-<10-<(tert-butyldiphenylsilyloxy)methyl>-8-methylene-1,4-dioxaspiro<4.5>decan-7-yl> 4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>heptane-1-carboxylate 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: 36.0%

: 116511-42-3
(-)-<1S(7S,8R,10S),4R>-<10-<(tert-butyldiphenylsilyloxy)methyl>-8-hydroxy-8-methyl-1,4-dioxaspiro<4.5>decan-7-yl> 4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>heptane-1-carboxylate

: 127818-24-0
(-)-<1S(7S,10S),4R>-<10-<(tert-butyldiphenylsilyloxy)methyl>-8-methylene-1,4-dioxaspiro<4.5>decan-7-yl> 4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>heptane-1-carboxylate

Guidance literature:: With thionyl chloride; In pyridine; at 0 ℃; for 1h;
DOI:10.1016/S0040-4020(01)89182-1

Reference yield:

: 127785-50-6
5-hydroxymethyl-4-methoxy-1-methyl-1,3-cyclohexadiene

: 127818-24-0
(-)-<1S(7S,10S),4R>-<10-<(tert-butyldiphenylsilyloxy)methyl>-8-methylene-1,4-dioxaspiro<4.5>decan-7-yl> 4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>heptane-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / 4-dimethylaminopyridine, triethylamine / CH₂Cl₂ / 18 h / 0 °C

2: 88 percent / pyridinium-p-toluenesulphonate / benzene / 16 h / Heating; Dean-Stark conditions

3: 71 percent / osmium tetroxide, N-methylmorpholine-N-oxide monohydrate / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2 h / Ambient temperature

4: 43 percent / 1.) triethylamine; 2.) 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 0 °C / 1.) 10 min

5: 36 percent / thionyl chloride / pyridine / 1 h / 0 °C

With dmap; osmium(VIII) oxide; thionyl chloride; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4020(01)89182-1

Reference yield:

: 116511-38-7
5-<(tert-butyldiphenylsilyloxy)methyl>-4-methoxy-1-methyl-1,3-cyclohexadiene

: 127818-24-0
(-)-<1S(7S,10S),4R>-<10-<(tert-butyldiphenylsilyloxy)methyl>-8-methylene-1,4-dioxaspiro<4.5>decan-7-yl> 4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>heptane-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / pyridinium-p-toluenesulphonate / benzene / 16 h / Heating; Dean-Stark conditions

2: 71 percent / osmium tetroxide, N-methylmorpholine-N-oxide monohydrate / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2 h / Ambient temperature

3: 43 percent / 1.) triethylamine; 2.) 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 0 °C / 1.) 10 min

4: 36 percent / thionyl chloride / pyridine / 1 h / 0 °C

With dmap; osmium(VIII) oxide; thionyl chloride; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4020(01)89182-1