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

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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-propionaldehyde
CAS No.:620949-12-4
Molecular Formula:C₅₀H₆₄O₉Si
Molecular Weight:837.138
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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-propionaldehyde

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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-propionaldehyde

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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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-propionaldehyde

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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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-propionaldehyde

There total 10 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-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yloxy)-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: 63.0%

: 620949-10-2
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)-propionitrile

: 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

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(03)01862-8

Reference yield:

: 620949-05-5
(4aR,6S,7R,8aS)-2,2-Di-tert-butyl-6-vinyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol

: 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

Guidance literature:: Multi-step reaction with 7 steps

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

1.2: 66 percent / aq. H₂O₂; aq. NaHCO₃

2.1: 11 percent / Sc(OTf)3 / benzene / 1.5 h

3.1: NaH; TBAI / tetrahydrofuran; dimethylformamide

4.1: 87 percent / TMSOTf; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 36 h / 20 °C

5.1: Bu₃P / tetrahydrofuran

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

7.1: 63 percent / DIBAL-H / CH₂Cl₂ / -78 °C

With 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:

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

: 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

Guidance literature:: Multi-step reaction with 8 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

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