1-[(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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-hex-5-en-3-ol

Base Information

Chemical Name:1-[(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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-hex-5-en-3-ol
CAS No.:620949-13-5
Molecular Formula:C₅₃H₇₀O₉Si
Molecular Weight:879.219
Hs Code.:

1-[(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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-hex-5-en-3-ol

Synonyms:1-[(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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-hex-5-en-3-ol

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Chemical Property of 1-[(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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-hex-5-en-3-ol

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Technology Process of 1-[(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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-hex-5-en-3-ol

There total 10 articles about 1-[(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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-hex-5-en-3-ol 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: 81.0%

: 620949-12-4
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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-propionaldehyde

: 1730-25-2
allylmagnesium bromide

: 620949-13-5
1-[(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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-hex-5-en-3-ol

Guidance literature:: In tetrahydrofuran; at -50 ℃; for 0.583333h;
DOI:10.1016/S0040-4039(03)01862-8

Reference yield:

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

: 620949-13-5
1-[(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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 9 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

6.1: Bu₃P / tetrahydrofuran

7.1: aq. H₂O₂; aq. NaHCO₃ / tetrahydrofuran / 40 °C

8.1: 63 percent / DIBAL-H / CH₂Cl₂ / -78 °C

9.1: 81 percent / tetrahydrofuran / 0.58 h / -50 °C

With 2,6-dimethylpyridine; 2,6-di-tert-butyl-4-methylpyridine; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 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

: 620949-13-5
1-[(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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 10 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

7.1: Bu₃P / tetrahydrofuran

8.1: aq. H₂O₂; aq. NaHCO₃ / tetrahydrofuran / 40 °C

9.1: 63 percent / DIBAL-H / CH₂Cl₂ / -78 °C

10.1: 81 percent / tetrahydrofuran / 0.58 h / -50 °C

With 2,6-dimethylpyridine; 2,6-di-tert-butyl-4-methylpyridine; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 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