(1R,3S,4R,6Z,9S,11S)-3-hydroxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-en-4-ol

Base Information

Chemical Name:(1R,3S,4R,6Z,9S,11S)-3-hydroxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-en-4-ol
CAS No.:876288-75-4
Molecular Formula:C₁₇H₂₂O₅
Molecular Weight:306.359
Hs Code.:

Synonyms:(1R,3S,4R,6Z,9S,11S)-3-hydroxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-en-4-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,3S,4R,6Z,9S,11S)-3-hydroxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-en-4-ol

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Technology Process of (1R,3S,4R,6Z,9S,11S)-3-hydroxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-en-4-ol

There total 1 articles about (1R,3S,4R,6Z,9S,11S)-3-hydroxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-en-4-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: 98.0%

: 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

: 876288-75-4
(1R,3S,4R,6Z,9S,11S)-3-hydroxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-en-4-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 1h;
DOI:10.1016/j.tet.2006.05.014

Reference yield: 98.0%

: 876288-75-4
(1R,3S,4R,6Z,9S,11S)-3-hydroxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-en-4-ol

: 100-39-0
benzyl bromide

: 876288-76-5
(1R,3S,4R,6Z,9S,11S)-4-benzyloxy-3-benzyloxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-ene

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 - 25 ℃; for 0.375h;
DOI:10.1016/j.tet.2006.05.014

Reference yield:

: 876288-75-4
(1R,3S,4R,6Z,9S,11S)-3-hydroxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-en-4-ol

: 876288-83-4
5-[8-benzyloxy-9-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-1-[7-(4-bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-3-methyl-pent-3-en-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 98 percent / NaH; TBAI / tetrahydrofuran / 0.38 h / 0 - 25 °C

2.1: 98 percent / aq. HCl / tetrahydrofuran / 21 h / 25 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

4.1: 17.5 mg / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 - 0 °C

5.1: BuLi / tetrahydrofuran / 0.17 h / -78 °C

5.2: 99 percent / tetrahydrofuran / 3 h / -78 - 24 °C

6.1: Cp₂ZrCl₂; DIBAL / tetrahydrofuran; hexane / 0.5 h / 55 °C

6.2: 86 percent / I₂ / tetrahydrofuran; hexane / 0.25 h / 0 °C

7.1: 45 percent / CrCl₂; NiCl₂ / dimethylsulfoxide / 25 h / 25 °C

With 2,6-dimethylpyridine; chromium dichloride; hydrogenchloride; n-butyllithium; zirconocene dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; nickel dichloride; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 7.1: Nozaki-Hiyama-Kishi reaction;
DOI:10.1016/j.tet.2006.05.014