(5S,6S,7R)-(E)-8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,7-dimethyl-3-octene

Base Information

Chemical Name:(5S,6S,7R)-(E)-8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,7-dimethyl-3-octene
CAS No.:313696-86-5
Molecular Formula:C₃₃H₄₄O₃Si
Molecular Weight:516.796
Hs Code.:

Synonyms:(5S,6S,7R)-(E)-8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,7-dimethyl-3-octene

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Chemical Property of (5S,6S,7R)-(E)-8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,7-dimethyl-3-octene

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Technology Process of (5S,6S,7R)-(E)-8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,7-dimethyl-3-octene

There total 1 articles about (5S,6S,7R)-(E)-8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,7-dimethyl-3-octene 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:

: 79026-61-2
(R)-3-benzyloxy-2-methylpropanal

: (4S)-(E)-6-(tert-butyldiphenylsilyloxy)-4-(dimethylphenyl)silyl-2-hexene

: (7R)-(E)-8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,7-dimethyl-3-octene

: 313696-86-5
(5S,6S,7R)-(E)-8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,7-dimethyl-3-octene

Guidance literature:: With titanium tetrachloride; In dichloromethane; at -78 ℃; for 5h; Title compound not separated from byproducts.;
DOI:10.1021/ja002377a

Reference yield: 90.0%

: 313696-86-5
(5S,6S,7R)-(E)-8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,7-dimethyl-3-octene

: 313696-87-6
(5S,6S,7R)-(E)-1-(tert-butyldiphenylsilyloxy)-6,8-dihydroxy-5,7-dimethyl-3-octene

Guidance literature:: With boron trichloride; In hexane; toluene; at -78 ℃; for 5h;
DOI:10.1021/ja002377a

Reference yield:

: 313696-86-5
(5S,6S,7R)-(E)-8-benzyloxy-1-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,7-dimethyl-3-octene

: C₆₁H₇₉N₃O₁₄Si

Guidance literature:: Multi-step reaction with 17 steps

1.1: 90 percent / boron trichloride / toluene; hexane / 5 h / -78 °C

2.1: 89 percent / p-toluene sulfonic acid monohydrade / benzene / 20 h / 25 °C

3.1: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 15 h / -50 °C

4.1: 98 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h / 20 °C

5.1: LDA / tetrahydrofuran; hexane / 0.5 h / -10 °C

6.1: 2.75 g / PPTS / benzene / 5 h / Heating

7.1: 77 percent / O₃; pyridine; methyl sulfide / methanol; CH₂Cl₂ / 15 h / -78 - 25 °C

8.1: 88 percent / NiCl₂; CrCl₂ / tetrahydrofuran; dimethylsulfoxide / 20 °C

9.1: NaNO₂; H₂ / PtO₂ / ethyl acetate; ethanol / 3 h / 3040.2 Torr

10.1: DIBAL-H / CH₂Cl₂; hexane / 2 h / -78 °C

11.1: 411 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1.5 h / 20 °C

12.1: 87 percent / aq. DDQ / CH₂Cl₂ / 0.75 h / 20 °C

13.1: 82 percent / DMAP / CH₂Cl₂ / 0.5 h / 0 °C

14.1: triethylphosphine / dimethylformamide / 0.5 h / 20 °C

14.2: 86 percent / DBU / dimethylformamide; tetrahydrofuran / 0.5 h / 0 °C

15.1: 65 percent / PPTS / ethanol / 22 h / 50 °C

16.1: 2,4,6-trichlorobenzoyl chloride; diisopropylethyl amine / benzene / 10 h / 20 °C

16.2: 66 percent / DMAP / benzene

17.1: PPTS / acetone; H₂O / 120 h / Heating

With pyridine; chromium dichloride; dmap; dimethylsulfide; 2,4,6-trichlorobenzoyl chloride; hydrogen; pyridinium p-toluenesulfonate; boron trichloride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; lithium diisopropyl amide; sodium nitrite; triethylphosphine; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene; 14.1: Schlosser-Wittig olefination / 16.1: Yonemitsu/Yamaguchi reaction;
DOI:10.1021/ja002377a