(2R,3S,4aR,6R,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)-7-methylenehexahydro-1,5-dioxabenzocycloheptane

Base Information

Chemical Name:(2R,3S,4aR,6R,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)-7-methylenehexahydro-1,5-dioxabenzocycloheptane
CAS No.:632354-49-5
Molecular Formula:C₄₂H₅₀O₅Si
Molecular Weight:662.942
Hs Code.:

(2R,3S,4aR,6R,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)-7-methylenehexahydro-1,5-dioxabenzocycloheptane

Synonyms:(2R,3S,4aR,6R,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)-7-methylenehexahydro-1,5-dioxabenzocycloheptane

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Chemical Property of (2R,3S,4aR,6R,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)-7-methylenehexahydro-1,5-dioxabenzocycloheptane

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Technology Process of (2R,3S,4aR,6R,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)-7-methylenehexahydro-1,5-dioxabenzocycloheptane

There total 1 articles about (2R,3S,4aR,6R,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)-7-methylenehexahydro-1,5-dioxabenzocycloheptane 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: 91.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 632354-44-0
(2R,3S,4aR,6S,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)hexahydro-1,5-dioxabenzocycloheptan-7-one

: 632354-49-5
(2R,3S,4aR,6R,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)-7-methylenehexahydro-1,5-dioxabenzocycloheptane

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;
DOI:10.1021/jo035145d

Reference yield: 65.0%

: 632354-49-5
(2R,3S,4aR,6R,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)-7-methylenehexahydro-1,5-dioxabenzocycloheptane

: 632354-50-8
(2R,3S,4aR,6S,7S,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)hexahydro-1,5-dioxabenzocycloheptane-7-spiro-2'-oxirane

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In toluene; at 20 ℃; for 3h;
DOI:10.1021/jo035145d

Reference yield:

: 632354-49-5
(2R,3S,4aR,6R,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)-7-methylenehexahydro-1,5-dioxabenzocycloheptane

: 632354-59-7
C₅₆H₈₈O₁₂Si₂

Guidance literature:: Multi-step reaction with 15 steps

1: 65 percent / m-CPBA; NaHCO₃ / toluene / 3 h / 20 °C

2: 96 percent / LiBEt₃ / tetrahydrofuran / 0.67 h / 0 °C

3: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

4: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

5: 1.32 g / 2,6-lutidine / CH₂Cl₂ / 0.75 h

6: 90 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 0.5 h / -100 °C

7: 90 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 20 °C

8: 98 percent / NaBH₄ / CH₂Cl₂; methanol / 0.5 h / 0 °C

9: 100 percent / TBAF / tetrahydrofuran / 1.17 h / 20 °C

10: PPTS / tetrahydrofuran / 0.75 h / Heating

11: H₂ / Pd(OH)2/C / tetrahydrofuran / 1 h / 20 °C

12: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

13: 805 mg / 2,6-lutidine / CH₂Cl₂ / 0.75 h

14: 80 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 0.5 h / -78 °C

15: 80 percent / RuO₂*H₂O; NaIO₄ / CCl₄; acetonitrile; H₂O / 1 h / 20 °C

With 2,6-dimethylpyridine; ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; lithium triethylborohydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jo035145d