2-((4aR,6S,7R,8aS)-6-Allyl-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-3-[(2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propionaldehyde

Base Information

Chemical Name:2-((4aR,6S,7R,8aS)-6-Allyl-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-3-[(2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propionaldehyde
CAS No.:855300-19-5
Molecular Formula:C₅₃H₇₀O₉Si
Molecular Weight:879.219
Hs Code.:

2-((4aR,6S,7R,8aS)-6-Allyl-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-3-[(2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propionaldehyde

Synonyms:2-((4aR,6S,7R,8aS)-6-Allyl-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-3-[(2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propionaldehyde

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Chemical Property of 2-((4aR,6S,7R,8aS)-6-Allyl-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-3-[(2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propionaldehyde

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Technology Process of 2-((4aR,6S,7R,8aS)-6-Allyl-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-3-[(2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propionaldehyde

There total 9 articles about 2-((4aR,6S,7R,8aS)-6-Allyl-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-3-[(2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propionaldehyde 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: 88.0%

: 855300-13-9
2-((4aR,6S,7R,8aS)-6-Allyl-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-3-[(2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propionitrile

: 855300-19-5
2-((4aR,6S,7R,8aS)-6-Allyl-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-3-[(2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propionaldehyde

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;
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

: 855300-19-5
2-((4aR,6S,7R,8aS)-6-Allyl-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-3-[(2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propionaldehyde

Guidance literature:: Multi-step reaction with 8 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

With water; hydrogen; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; scandium tris(trifluoromethanesulfonate); palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene; 7.1: Wittig olefination;
DOI:10.1016/j.tetlet.2005.04.040

Reference yield:

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

: 855300-19-5
2-((4aR,6S,7R,8aS)-6-Allyl-2,2-di-tert-butyl-4a,6-dimethyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-3-[(2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-propionaldehyde

Guidance literature:: Multi-step reaction with 9 steps

1.1: 85 percent / 2,6-lutidine / dimethylformamide; tetrahydrofuran

2.1: 81 percent / H₂ / Pd/C / ethyl acetate; methanol

3.1: 92 percent / Sc(OTf)3 / benzene / 1.5 h

4.1: DDQ; H₂O / CH₂Cl₂

5.1: NaHMDS; TBAI / tetrahydrofuran; dimethylformamide

6.1: Sc(OTf)3 / CH₂Cl₂ / 58 h / 20 °C

6.2: 89 percent / K₂CO₃; MeOH

7.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h

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

9.1: 88 percent / DIBAL-H / CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; water; hydrogen; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; scandium tris(trifluoromethanesulfonate); palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene; 8.1: Wittig olefination;
DOI:10.1016/j.tetlet.2005.04.040