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

Base Information

Chemical Name:3-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-2-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-4a,6-dimethyl-6-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-propionitrile
CAS No.:855300-12-8
Molecular Formula:C₅₂H₆₇NO₈Si
Molecular Weight:862.191
Hs Code.:

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

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

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

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

There total 8 articles about 3-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-2-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-4a,6-dimethyl-6-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-propionitrile 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: 57.0%

: 855300-17-3
3-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-2-[(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-yloxy]-propionitrile

: 855300-12-8
3-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-2-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-4a,6-dimethyl-6-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-propionitrile

Guidance literature:: 3-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-2-[(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-yloxy]-propionitrile; With ortho-nitrophenyl selenocyanate; tributylphosphine; In tetrahydrofuran;

With dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; at 45 ℃;
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

: 855300-12-8
3-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-2-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-4a,6-dimethyl-6-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-propionitrile

Guidance literature:: Multi-step reaction with 6 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: 2-NO₂C₆H₄SeCN; Bu₃P / tetrahydrofuran

6.2: 57 percent / aq. H₂O₂; aq. NaHCO₃ / tetrahydrofuran / 45 °C

With ortho-nitrophenyl selenocyanate; tributylphosphine; water; hydrogen; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; 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;
DOI:10.1016/j.tetlet.2005.04.040

Reference yield:

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

: 855300-12-8
3-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl]-2-((4aR,6S,7R,8aS)-2,2-di-tert-butyl-4a,6-dimethyl-6-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-propionitrile

Guidance literature:: Multi-step reaction with 7 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: 2-NO₂C₆H₄SeCN; Bu₃P / tetrahydrofuran

7.2: 57 percent / aq. H₂O₂; aq. NaHCO₃ / tetrahydrofuran / 45 °C

With 2,6-dimethylpyridine; ortho-nitrophenyl selenocyanate; tributylphosphine; water; hydrogen; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; 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;
DOI:10.1016/j.tetlet.2005.04.040