(2S,3R,5Z,8S,9R)-8-benzyloxy-9-benzyloxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonin-3-ol

Base Information

Chemical Name:(2S,3R,5Z,8S,9R)-8-benzyloxy-9-benzyloxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonin-3-ol
CAS No.:792919-86-9
Molecular Formula:C₂₅H₃₀O₄
Molecular Weight:394.511
Hs Code.:

Synonyms:(2S,3R,5Z,8S,9R)-8-benzyloxy-9-benzyloxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonin-3-ol

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Chemical Property of (2S,3R,5Z,8S,9R)-8-benzyloxy-9-benzyloxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonin-3-ol

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Technology Process of (2S,3R,5Z,8S,9R)-8-benzyloxy-9-benzyloxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonin-3-ol

There total 7 articles about (2S,3R,5Z,8S,9R)-8-benzyloxy-9-benzyloxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonin-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:

: ((Z)-(2S,3R,8S,9R)-8-Benzyloxy-9-benzyloxymethyl-2-vinyl-2,3,4,7,8,9-hexahydro-oxonin-3-yloxy)-tert-butyl-dimethyl-silane

: 792919-86-9
(2S,3R,5Z,8S,9R)-8-benzyloxy-9-benzyloxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonin-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 18h;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 100-39-0
benzyl bromide

: 792919-86-9
(2S,3R,5Z,8S,9R)-8-benzyloxy-9-benzyloxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonin-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: NaH; TBAI / tetrahydrofuran / 15 h / 24 °C

2: 135.8 mg / TBAF / tetrahydrofuran / 18 h / 25 °C

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 475641-59-9
(Z)-(2R,4aR,6S,7R,11aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxa-benzocyclononene

: 792919-86-9
(2S,3R,5Z,8S,9R)-8-benzyloxy-9-benzyloxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonin-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 24 percent / TFA; H₂O / tetrahydrofuran / 4 h / 0 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -20 °C

3.1: NaHMDS / tetrahydrofuran / 1 h / 24 °C

3.2: tetrahydrofuran / 2.5 h / -78 °C

4.1: 113.5 mg / 1,2-ethanedithiol; NaHCL₃; Zn(OTf)2 / CH₂Cl₂ / 2.5 h / 0 °C

5.1: NaH; TBAI / tetrahydrofuran / 15 h / 24 °C

6.1: 135.8 mg / TBAF / tetrahydrofuran / 18 h / 25 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; ethane-1,2-dithiol; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 3.2: Wittig reaction;
DOI:10.1016/j.tet.2005.05.073