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

Base Information

Chemical Name:(2R,3S,4aR,6S,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)hexahydro-1,5-dioxabenzocycloheptan-7-one
CAS No.:632354-44-0
Molecular Formula:C₄₁H₄₈O₆Si
Molecular Weight:664.914
Hs Code.:

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

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

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

There total 1 articles about (2R,3S,4aR,6S,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)hexahydro-1,5-dioxabenzocycloheptan-7-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: 60.0%

: 18107-18-1
diazomethyl-trimethyl-silane

: 632354-43-9
(2S,4aS,6R,7S,8aR)-7-benzyloxy-6-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)octahydropyrano[3,2-b]pyran-3-one

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

: (2R,3S,4aR,6S,9aS)-3-benzyloxy-2-benzyloxymethyl-6-(tert-butyldiphenylsilyloxymethyl)hexahydro-1,5-dioxabenzocycloheptan-8-one

: C₄₄H₅₆O₆Si₂

Guidance literature:: diazomethyl-trimethyl-silane; (2S,4aS,6R,7S,8aR)-7-benzyloxy-6-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)octahydropyrano[3,2-b]pyran-3-one; With 3 A molecular sieve; boron trifluoride diethyl etherate; In hexane; dichloromethane; at -78 ℃; for 0.666667h;

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1021/jo035145d

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:

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

: C₄₁H₅₆O₁₀

Guidance literature:: Multi-step reaction with 17 steps

1.1: 91 percent / KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.1: 65 percent / m-CPBA; NaHCO₃ / toluene / 3 h / 20 °C

3.1: 96 percent / LiBEt₃ / tetrahydrofuran / 0.67 h / 0 °C

4.1: 100 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 1.32 g / 2,6-lutidine / CH₂Cl₂ / 0.75 h

7.1: 90 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 0.5 h / -100 °C

8.1: 90 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 20 °C

9.1: 98 percent / NaBH₄ / CH₂Cl₂; methanol / 0.5 h / 0 °C

10.1: 100 percent / TBAF / tetrahydrofuran / 1.17 h / 20 °C

11.1: PPTS / tetrahydrofuran / 0.75 h / Heating

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

13.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

14.1: 805 mg / 2,6-lutidine / CH₂Cl₂ / 0.75 h

15.1: 80 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 0.5 h / -78 °C

16.1: 80 percent / RuO₂*H₂O; NaIO₄ / CCl₄; acetonitrile; H₂O / 1 h / 20 °C

17.1: CSA; HC(OMe)3 / methanol / 13.5 h / 20 - 80 °C

17.2: 144 mg / Et₃SiH; TMSOTf / CH₂Cl₂ / 1.5 h / 0 °C

With 2,6-dimethylpyridine; ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; lithium triethylborohydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; trimethyl orthoformate; palladium dihydroxide; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jo035145d