(4aR,5aS,10S,11aR,12aS)-10-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-4a,5a-dimethyl-octahydro-1,3,5,11-tetraoxa-2-sila-cycloocta[b]naphthalen-9-one

Base Information

Chemical Name:(4aR,5aS,10S,11aR,12aS)-10-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-4a,5a-dimethyl-octahydro-1,3,5,11-tetraoxa-2-sila-cycloocta[b]naphthalen-9-one
CAS No.:855300-27-5
Molecular Formula:C₅₃H₇₀O₉Si
Molecular Weight:879.219
Hs Code.:

(4aR,5aS,10S,11aR,12aS)-10-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-4a,5a-dimethyl-octahydro-1,3,5,11-tetraoxa-2-sila-cycloocta[b]naphthalen-9-one

Synonyms:(4aR,5aS,10S,11aR,12aS)-10-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-4a,5a-dimethyl-octahydro-1,3,5,11-tetraoxa-2-sila-cycloocta[b]naphthalen-9-one

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Chemical Property of (4aR,5aS,10S,11aR,12aS)-10-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-4a,5a-dimethyl-octahydro-1,3,5,11-tetraoxa-2-sila-cycloocta[b]naphthalen-9-one

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Technology Process of (4aR,5aS,10S,11aR,12aS)-10-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-4a,5a-dimethyl-octahydro-1,3,5,11-tetraoxa-2-sila-cycloocta[b]naphthalen-9-one

There total 14 articles about (4aR,5aS,10S,11aR,12aS)-10-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-4a,5a-dimethyl-octahydro-1,3,5,11-tetraoxa-2-sila-cycloocta[b]naphthalen-9-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: 85.0%

: 10-[5-benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-4a,5a-dimethyl-4a,5a,8,11a,12,12a-hexahydro-4H-1,3,5,11-tetraoxa-2-sila-cycloocta[b]naphthalen-9-one

: 855300-27-5
(4aR,5aS,10S,11aR,12aS)-10-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-4a,5a-dimethyl-octahydro-1,3,5,11-tetraoxa-2-sila-cycloocta[b]naphthalen-9-one

Guidance literature:: With hydrogen; platinum(IV) oxide; In ethyl acetate; for 4h;
DOI:10.1016/j.tetlet.2005.04.040

Reference yield:

: 874188-24-6
(4aR,6S,7R,8aS)-2,2-Di-tert-butyl-6-(2-hydroxy-ethyl)-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol

: 855300-27-5
(4aR,5aS,10S,11aR,12aS)-10-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-4a,5a-dimethyl-octahydro-1,3,5,11-tetraoxa-2-sila-cycloocta[b]naphthalen-9-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: 92 percent / Sc(OTf)3 / benzene / 1.5 h

2.1: DDQ; H₂O / CH₂Cl₂

3.1: NaHMDS; TBAI / tetrahydrofuran; dimethylformamide

4.1: Sc(OTf)3 / CH₂Cl₂ / 58 h / 20 °C

4.2: 89 percent / K₂CO₃; MeOH

5.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h

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

7.1: 88 percent / DIBAL-H / CH₂Cl₂ / -78 °C

8.1: 80 percent / MeLi / tetrahydrofuran / -78 °C

9.1: Dess-Martin periodinane / CH₂Cl₂

9.2: 66 percent / Grubbs catalyst 2. generation / toluene / 3 h / 100 °C

10.1: 54 percent / DBU / toluene / 18 h / Heating

11.1: 85 percent / hydrogen / PtO₂ / ethyl acetate / 4 h

With 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; scandium tris(trifluoromethanesulfonate); platinum(IV) oxide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 6.1: Wittig olefination;
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

: 855300-27-5
(4aR,5aS,10S,11aR,12aS)-10-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-4a,5a-dimethyl-octahydro-1,3,5,11-tetraoxa-2-sila-cycloocta[b]naphthalen-9-one

Guidance literature:: Multi-step reaction with 12 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

With 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; 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