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)-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-6-(2-hydroxy-ethyl)-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy]-propionitrile
CAS No.:620949-32-8
Molecular Formula:C₅₀H₆₅NO₉Si
Molecular Weight:852.153
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-6-(2-hydroxy-ethyl)-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-6-(2-hydroxy-ethyl)-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-6-(2-hydroxy-ethyl)-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-6-(2-hydroxy-ethyl)-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy]-propionitrile

There total 7 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-6-(2-hydroxy-ethyl)-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: 87.0%

: 7677-24-9
trimethylsilyl cyanide

: 620949-09-9
(4aR,5aS,10aR,11aS)-9-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-ylmethyl]-2,2-di-tert-butyl-octahydro-1,3,5,8,10-pentaoxa-2-sila-cyclohepta[b]naphthalene

: 620949-32-8
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-6-(2-hydroxy-ethyl)-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy]-propionitrile

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 36h;
DOI:10.1016/S0040-4039(03)01862-8

Reference yield:

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

: 620949-32-8
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-6-(2-hydroxy-ethyl)-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy]-propionitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-lutidine / dimethylformamide / 0.5 h / 0 °C

2.1: catecholborane / Rh(PPh₃)3Cl / tetrahydrofuran / 14 h / 20 °C

2.2: 66 percent / aq. H₂O₂; aq. NaHCO₃

3.1: 11 percent / Sc(OTf)3 / benzene / 1.5 h

4.1: NaH; TBAI / tetrahydrofuran; dimethylformamide

5.1: 87 percent / TMSOTf; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 36 h / 20 °C

With 2,6-dimethylpyridine; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; scandium tris(trifluoromethanesulfonate); benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(03)01862-8

Reference yield:

: 602301-65-5
(2R,4aR,6S,7R,8aS)-2-(4-Methoxy-phenyl)-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 620949-32-8
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-6-(2-hydroxy-ethyl)-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy]-propionitrile

Guidance literature:: Multi-step reaction with 6 steps

1.1: p-TsOH / methanol; H₂O / 0.5 h / 20 °C

2.1: 2,6-lutidine / dimethylformamide / 0.5 h / 0 °C

3.1: catecholborane / Rh(PPh₃)3Cl / tetrahydrofuran / 14 h / 20 °C

3.2: 66 percent / aq. H₂O₂; aq. NaHCO₃

4.1: 11 percent / Sc(OTf)3 / benzene / 1.5 h

5.1: NaH; TBAI / tetrahydrofuran; dimethylformamide

6.1: 87 percent / TMSOTf; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 36 h / 20 °C

With 2,6-dimethylpyridine; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; scandium tris(trifluoromethanesulfonate); benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(03)01862-8