(2R,8R,9R)-(8-benzyloxy-9-benzyloxymethyl-4,8-dimethyl-2,3,6,7,8,9-hexahydro-oxonin-2-yl)-methanol

Base Information

Chemical Name:(2R,8R,9R)-(8-benzyloxy-9-benzyloxymethyl-4,8-dimethyl-2,3,6,7,8,9-hexahydro-oxonin-2-yl)-methanol
CAS No.:758716-31-3
Molecular Formula:C₂₆H₃₄O₄
Molecular Weight:410.554
Hs Code.:

Synonyms:(2R,8R,9R)-(8-benzyloxy-9-benzyloxymethyl-4,8-dimethyl-2,3,6,7,8,9-hexahydro-oxonin-2-yl)-methanol

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Chemical Property of (2R,8R,9R)-(8-benzyloxy-9-benzyloxymethyl-4,8-dimethyl-2,3,6,7,8,9-hexahydro-oxonin-2-yl)-methanol

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Technology Process of (2R,8R,9R)-(8-benzyloxy-9-benzyloxymethyl-4,8-dimethyl-2,3,6,7,8,9-hexahydro-oxonin-2-yl)-methanol

There total 15 articles about (2R,8R,9R)-(8-benzyloxy-9-benzyloxymethyl-4,8-dimethyl-2,3,6,7,8,9-hexahydro-oxonin-2-yl)-methanol 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: 89.0%

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

: 758716-31-3
(2R,8R,9R)-(8-benzyloxy-9-benzyloxymethyl-4,8-dimethyl-2,3,6,7,8,9-hexahydro-oxonin-2-yl)-methanol

Guidance literature:: With Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; In benzene; at 80 ℃; for 5h;
DOI:10.1021/ja046574b

Reference yield: 60.0%

: 919096-87-0
8-benzyloxy-9-benzyloxymethyl-4,8-dimethyl-2,3,6,7,8,9-hexahydro-oxonine-2-carboxylic acid dimethylamide

: 758716-31-3
(2R,8R,9R)-(8-benzyloxy-9-benzyloxymethyl-4,8-dimethyl-2,3,6,7,8,9-hexahydro-oxonin-2-yl)-methanol

Guidance literature:: With Super-H; In tetrahydrofuran; toluene; at 20 ℃; for 2h;
DOI:10.1021/ja065782w

Reference yield:

: 109613-59-4
(S)-1-(benzyloxy)but-3-en-2-ol

: 758716-31-3
(2R,8R,9R)-(8-benzyloxy-9-benzyloxymethyl-4,8-dimethyl-2,3,6,7,8,9-hexahydro-oxonin-2-yl)-methanol

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 95 percent / tetrahydrofuran; dimethylformamide / 20 °C

2.1: aq. mercuric acetate / tetrahydrofuran / 12 h / 20 °C

2.2: 89 percent / aq. CuCl₂; LiCl; PdCl₂ / tetrahydrofuran / 3 h / 55 °C

3.1: 92 percent / tetrahydrofuran / 2 h / -78 °C

4.1: KH / tetrahydrofuran / 0.5 h / 0 °C

4.2: 92 percent / tetrahydrofuran; dimethylformamide / 20 °C

5.1: 83 percent / aq. HCl / methanol / 2 h / Heating

6.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

6.2: 97 percent / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

7.1: Et₃N / tetrahydrofuran / 1 h / -78 - 0 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

8.2: 33.9 g / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C

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

9.2: 93 percent / tetrahydrofuran; toluene / 1.25 h / -78 - -45 °C

10.1: 92 percent / lithium borohydride / methanol; diethyl ether; tetrahydrofuran / 1 h / 0 °C

11.1: 89 percent / Cl₂(Cy₃P)(sIMes)Ru=CHPh / benzene / 5 h / 80 °C

With hydrogenchloride; lithium borohydride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; mercury(II) diacetate; sodium hexamethyldisilazane; potassium hydride; sodium hydride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; toluene; benzene;
DOI:10.1021/ja056334b