(4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalene

Base Information

Chemical Name:(4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalene
CAS No.:855300-14-0
Molecular Formula:C₃₂H₄₈O₅Si
Molecular Weight:540.816
Hs Code.:

Synonyms:(4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalene

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Chemical Property of (4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalene

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Technology Process of (4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalene

There total 1 articles about (4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalene 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: 85.0%

: 85272-31-7
di-tert-butylsilyl bis(trifluoromethanesulfonate)

: 170706-73-7
(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-hydroxymethyl-2,6-dimethyl-tetrahydro-pyran-3-ol

: 855300-14-0
(4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalene

Guidance literature:: With 2,6-dimethylpyridine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2005.04.040

Reference yield:

: 855300-14-0
(4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalene

: (2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((4aR,5aS,10aR,11aS)-2,2-di-tert-butyl-4a,5a-dimethyl-octahydro-1,3,5,8,10-pentaoxa-2-sila-cyclohepta[b]naphthalen-9-ylmethyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / H₂ / Pd/C / ethyl acetate; methanol

2: 92 percent / Sc(OTf)3 / benzene / 1.5 h

3: DDQ; H₂O / CH₂Cl₂

With water; hydrogen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; scandium tris(trifluoromethanesulfonate); palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; benzene;
DOI:10.1016/j.tetlet.2005.04.040

Reference yield:

: 855300-14-0
(4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalene

: C₄₃H₆₄O₈Si

Guidance literature:: Multi-step reaction with 15 steps

1.1: 81 percent / H₂ / Pd/C / ethyl acetate; methanol

2.1: 92 percent / Sc(OTf)3 / benzene / 1.5 h

3.1: DDQ; H₂O / CH₂Cl₂

4.1: NaHMDS; TBAI / tetrahydrofuran; dimethylformamide

5.1: Sc(OTf)3 / CH₂Cl₂ / 58 h / 20 °C

5.2: 89 percent / K₂CO₃; MeOH

6.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h

7.1: NaHMDS / tetrahydrofuran / 0.67 h / 0 °C

8.1: 88 percent / DIBAL-H / CH₂Cl₂ / -78 °C

9.1: 80 percent / MeLi / tetrahydrofuran / -78 °C

10.1: Dess-Martin periodinane / CH₂Cl₂

10.2: 66 percent / Grubbs catalyst 2. generation / toluene / 3 h / 100 °C

11.1: 54 percent / DBU / toluene / 18 h / Heating

12.1: 85 percent / hydrogen / PtO₂ / ethyl acetate / 4 h

13.1: 61 percent / LHMDS / tetrahydrofuran / 5 h / -78 - -20 °C

14.1: DDQ; H₂O / CH₂Cl₂

15.1: Et₃SiH; TMSOTf / CH₂Cl₂ / 1 h / -60 - -30 °C

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; water; methyllithium; hydrogen; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; scandium tris(trifluoromethanesulfonate); platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 7.1: Wittig olefination;
DOI:10.1016/j.tetlet.2005.04.040