(E)-(2R,3R,4R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-ethyl-2-methyl-oct-5-en-1-ol

Base Information

Chemical Name:(E)-(2R,3R,4R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-ethyl-2-methyl-oct-5-en-1-ol
CAS No.:872615-36-6
Molecular Formula:C₃₅H₄₈O₃Si
Molecular Weight:544.85
Hs Code.:

Synonyms:(E)-(2R,3R,4R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-ethyl-2-methyl-oct-5-en-1-ol

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Chemical Property of (E)-(2R,3R,4R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-ethyl-2-methyl-oct-5-en-1-ol

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Technology Process of (E)-(2R,3R,4R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-ethyl-2-methyl-oct-5-en-1-ol

There total 9 articles about (E)-(2R,3R,4R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-ethyl-2-methyl-oct-5-en-1-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: 84.0%

: 872615-35-5
((E)-(4R,5R,6R)-5-Benzyloxy-2,4-diethyl-7-methoxymethoxy-6-methyl-hept-2-enyloxy)-tert-butyl-diphenyl-silane

: 872615-36-6
(E)-(2R,3R,4R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-ethyl-2-methyl-oct-5-en-1-ol

Guidance literature:: With 1,3 dithiane; boron trifluoride diethyl etherate;
DOI:10.1021/ol0521329

Reference yield:

: 872615-26-4
(E)-(S)-5-Methoxymethoxy-4-methyl-pent-2-en-1-ol

: 872615-36-6
(E)-(2R,3R,4R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-ethyl-2-methyl-oct-5-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: TBHP; Ti(O-iPr)4; D-tartaric acid diethyl ester / -23 °C

2: 62 percent / CuI / diethyl ether / -50 - -40 °C

3: 52 percent / RuCl₂(PPh₃)3 / benzene

4: 76 percent / benzene / Heating

5: 84 percent / NaH / tetrahydrofuran

6: 94 percent / DIBAL-H

7: 91 percent / triethylamine

8: 84 percent / 1,3-dithiane; BF₃*Et₂O

With 1,3 dithiane; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; tris(triphenylphosphine)ruthenium(II) chloride; diethyl (2S,3S)-tartrate; boron trifluoride diethyl etherate; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; benzene; 4: Horner-Wittig reaction;
DOI:10.1021/ol0521329

Reference yield:

: 872615-24-2
(E)-(S)-5-Methoxymethoxy-4-methyl-pent-2-enoic acid methyl ester

: 872615-36-6
(E)-(2R,3R,4R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-ethyl-2-methyl-oct-5-en-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2: TBHP; Ti(O-iPr)4; D-tartaric acid diethyl ester / -23 °C

3: 62 percent / CuI / diethyl ether / -50 - -40 °C

4: 52 percent / RuCl₂(PPh₃)3 / benzene

5: 76 percent / benzene / Heating

6: 84 percent / NaH / tetrahydrofuran

7: 94 percent / DIBAL-H

8: 91 percent / triethylamine

9: 84 percent / 1,3-dithiane; BF₃*Et₂O

With 1,3 dithiane; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; tris(triphenylphosphine)ruthenium(II) chloride; diethyl (2S,3S)-tartrate; boron trifluoride diethyl etherate; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; benzene; 5: Horner-Wittig reaction;
DOI:10.1021/ol0521329