(4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-di-tert-butyl-7-methyl-hexahydro-1,3,5-trioxa-2-sila-benzocycloheptene

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Chemical Name:(4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-di-tert-butyl-7-methyl-hexahydro-1,3,5-trioxa-2-sila-benzocycloheptene
CAS No.:440635-13-2
Molecular Formula:C₃₁H₄₆O₅Si
Molecular Weight:526.789
Hs Code.:

Synonyms:(4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-di-tert-butyl-7-methyl-hexahydro-1,3,5-trioxa-2-sila-benzocycloheptene

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Chemical Property of (4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-di-tert-butyl-7-methyl-hexahydro-1,3,5-trioxa-2-sila-benzocycloheptene

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Technology Process of (4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-di-tert-butyl-7-methyl-hexahydro-1,3,5-trioxa-2-sila-benzocycloheptene

There total 14 articles about (4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-di-tert-butyl-7-methyl-hexahydro-1,3,5-trioxa-2-sila-benzocycloheptene 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%

: 100-39-0
benzyl bromide

: 440635-19-8
(4aR,6S,7R,9aS)-2,2-Di-tert-butyl-6-hydroxymethyl-7-methyl-hexahydro-1,3,5-trioxa-2-sila-benzocyclohepten-7-ol

: 440635-13-2
(4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-di-tert-butyl-7-methyl-hexahydro-1,3,5-trioxa-2-sila-benzocycloheptene

Guidance literature:: With potassium hydride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(02)00038-8

Reference yield:

: 391235-59-9
(4S,5R)-2,2-di-tert-butyl-5-hydroxy-1,3-dioxa-2-silacyclohexane-4-methanol

: 440635-13-2
(4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-di-tert-butyl-7-methyl-hexahydro-1,3,5-trioxa-2-sila-benzocycloheptene

Guidance literature:: Multi-step reaction with 14 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 2.59 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

3.1: 91 percent / HMPA; n-BuLi / tetrahydrofuran; hexane / 0.67 h / -100 °C

4.1: 98 percent / TsOH*H₂O / methanol / 2 h / 20 °C

5.1: 97 percent / MgBr₂*Et₂O / CH₂Cl₂ / 1 h / 20 °C

6.1: 83 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

7.1: H₂ / 20 percent Pd(OH)2/C / ethyl acetate / 1 h

8.1: 1.26 g / imidazole / dimethylformamide / 3 h / 20 °C

9.1: BF₃*OEt₂; molecular sieves 3 Angstroem / CH₂Cl₂; hexane / 0.33 h / -78 °C

9.2: 72 percent / PPTS / methanol / 4 h / 20 °C

10.1: 95 percent / tetrahydrofuran; toluene / 0.58 h / 0 °C

11.1: 87 percent / 1,1,1-trifluoroacetone; Oxone(R); further reagents / acetonitrile; acetone / 5 h / 0 °C

12.1: 98 percent / LiBHEt₃ / tetrahydrofuran / 0.5 h / 0 °C

13.1: 88 percent / aq. KOH / methanol / 2.5 h / 20 °C

14.1: 96 percent / KH / tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; n-butyllithium; oxone; 1,1,1-trifluoro-2-propanone; 3 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; potassium hydride; lithium triethylborohydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4020(02)00038-8

Reference yield:

: 391235-78-2
(1S,6R,8S)-8-(benzyloxy)methyl-3,3-di-tert-butyl-2,4,7-trioxa-3-silabicyclo[4.4.0]deca-9-one

: 440635-13-2
(4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-di-tert-butyl-7-methyl-hexahydro-1,3,5-trioxa-2-sila-benzocycloheptene

Guidance literature:: Multi-step reaction with 8 steps

1.1: H₂ / 20 percent Pd(OH)2/C / ethyl acetate / 1 h

2.1: 1.26 g / imidazole / dimethylformamide / 3 h / 20 °C

3.1: BF₃*OEt₂; molecular sieves 3 Angstroem / CH₂Cl₂; hexane / 0.33 h / -78 °C

3.2: 72 percent / PPTS / methanol / 4 h / 20 °C

4.1: 95 percent / tetrahydrofuran; toluene / 0.58 h / 0 °C

5.1: 87 percent / 1,1,1-trifluoroacetone; Oxone(R); further reagents / acetonitrile; acetone / 5 h / 0 °C

6.1: 98 percent / LiBHEt₃ / tetrahydrofuran / 0.5 h / 0 °C

7.1: 88 percent / aq. KOH / methanol / 2.5 h / 20 °C

8.1: 96 percent / KH / tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; potassium hydroxide; oxone; 1,1,1-trifluoro-2-propanone; 3 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; potassium hydride; lithium triethylborohydride; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4020(02)00038-8