(2R,8R,9R)-8-benzyloxy-9-benzyloxymethyl-8-methyl-4-triisopropylsilanyloxymethyl-2,3,6,7,8,9-hexahydro-oxonine-2-carbaldehyde

Base Information

Chemical Name:(2R,8R,9R)-8-benzyloxy-9-benzyloxymethyl-8-methyl-4-triisopropylsilanyloxymethyl-2,3,6,7,8,9-hexahydro-oxonine-2-carbaldehyde
CAS No.:877374-60-2
Molecular Formula:C₃₅H₅₂O₅Si
Molecular Weight:580.88
Hs Code.:

Synonyms:(2R,8R,9R)-8-benzyloxy-9-benzyloxymethyl-8-methyl-4-triisopropylsilanyloxymethyl-2,3,6,7,8,9-hexahydro-oxonine-2-carbaldehyde

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Chemical Property of (2R,8R,9R)-8-benzyloxy-9-benzyloxymethyl-8-methyl-4-triisopropylsilanyloxymethyl-2,3,6,7,8,9-hexahydro-oxonine-2-carbaldehyde

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Technology Process of (2R,8R,9R)-8-benzyloxy-9-benzyloxymethyl-8-methyl-4-triisopropylsilanyloxymethyl-2,3,6,7,8,9-hexahydro-oxonine-2-carbaldehyde

There total 15 articles about (2R,8R,9R)-8-benzyloxy-9-benzyloxymethyl-8-methyl-4-triisopropylsilanyloxymethyl-2,3,6,7,8,9-hexahydro-oxonine-2-carbaldehyde 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:

: 877374-42-0
(2R,8R,9R)-(8-benzyloxy-9-benzyloxymethyl-8-methyl-4-triisopropylsilanyloxymethyl-2,3,6,7,8,9-hexahydro-oxonin-2-yl)-methanol

: 877374-60-2
(2R,8R,9R)-8-benzyloxy-9-benzyloxymethyl-8-methyl-4-triisopropylsilanyloxymethyl-2,3,6,7,8,9-hexahydro-oxonine-2-carbaldehyde

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ja056334b

Reference yield:

: 877374-30-6
(2-iodomethyl-allyloxy)-triisopropyl-silane

: 877374-60-2
(2R,8R,9R)-8-benzyloxy-9-benzyloxymethyl-8-methyl-4-triisopropylsilanyloxymethyl-2,3,6,7,8,9-hexahydro-oxonine-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

1.2: 94 percent / tetrahydrofuran; toluene / 1.25 h / -78 - -45 °C

2.1: 76 percent / lithium borohydride / methanol; diethyl ether / 1 h / 0 °C

3.1: Cl₂(Cy₃P)(sIMes)Ru=ChPh / hexane / 1 h / Heating

3.2: 88 percent / phenyl disulfide / benzene / 2 h / 20 °C / UV-irradiation

4.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

With pyridine; lithium borohydride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; sodium hexamethyldisilazane; Dess-Martin periodane; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; 3.1: Diels-Alder reaction;
DOI:10.1021/ja056334b

Reference yield:

: 877374-41-9
(2R)-2-[(1R,2R)-2-benzyloxy-1-benzyloxymethyl-2-methyl-hex-5-enyloxy]-4-triisopropylsilanyloxymethyl-pent-4-en-1-ol

: 877374-60-2
(2R,8R,9R)-8-benzyloxy-9-benzyloxymethyl-8-methyl-4-triisopropylsilanyloxymethyl-2,3,6,7,8,9-hexahydro-oxonine-2-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1.1: Cl₂(Cy₃P)(sIMes)Ru=ChPh / hexane / 1 h / Heating

1.2: 88 percent / phenyl disulfide / benzene / 2 h / 20 °C / UV-irradiation

2.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

With pyridine; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; Dess-Martin periodane; In hexane; dichloromethane; 1.1: Diels-Alder reaction;
DOI:10.1021/ja056334b