(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-2-((1Z,3E)-2-methyl-hepta-1,3,6-trienyl)-tetrahydro-pyran

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Chemical Name:(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-2-((1Z,3E)-2-methyl-hepta-1,3,6-trienyl)-tetrahydro-pyran
CAS No.:878132-07-1
Molecular Formula:C₃₈H₅₈O₃Si₂
Molecular Weight:619.048
Hs Code.:

(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-2-((1Z,3E)-2-methyl-hepta-1,3,6-trienyl)-tetrahydro-pyran

Synonyms:(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-2-((1Z,3E)-2-methyl-hepta-1,3,6-trienyl)-tetrahydro-pyran

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Chemical Property of (2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-2-((1Z,3E)-2-methyl-hepta-1,3,6-trienyl)-tetrahydro-pyran

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Technology Process of (2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-2-((1Z,3E)-2-methyl-hepta-1,3,6-trienyl)-tetrahydro-pyran

There total 13 articles about (2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-2-((1Z,3E)-2-methyl-hepta-1,3,6-trienyl)-tetrahydro-pyran 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: 90.0%

: 878131-85-2
(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((1Z,3E)-5-chloro-2-methyl-penta-1,3-dienyl)-3-methyl-tetrahydro-pyran

: 7486-35-3
tri-n-butyl(vinyl)tin

: 878132-07-1
(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-2-((1Z,3E)-2-methyl-hepta-1,3,6-trienyl)-tetrahydro-pyran

Guidance literature:: With tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; at 50 ℃; for 37h;
DOI:10.1021/ol0527678

Reference yield:

: (3S,4R,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-3-methyl-tetrahydro-pyran-2-one

: 878132-07-1
(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-2-((1Z,3E)-2-methyl-hepta-1,3,6-trienyl)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 12 steps

1: 91 percent / 2,6-lutidine / dimethylformamide / 3.5 h / 20 °C

2: 90 percent / nBuLi / tetrahydrofuran; hexane / 3 h / -78 °C

3: 90 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / -30 °C

4: 100 percent / H₂ / Pd/C / ethanol / 48 h

5: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

6: 88 percent / NaI; DBU / tetrahydrofuran / 1.75 h / -78 - 0 °C

7: 98 percent / DIBALH / CH₂Cl₂; hexane / 0.17 h / -78 °C

8: 99 percent / MnO₂ / CH₂Cl₂; benzene / 24 h / 20 °C

9: 94 percent / toluene / 43 h / 130 °C

10: 96 percent / DIBALH / CH₂Cl₂; hexane / 1.5 h / -78 °C

11: 100 percent / PPH₃; CCl₄ / CH₂Cl₂ / 0.5 h / 70 °C

12: 90 percent / (o-tolyl)3P / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 37 h / 50 °C

With 2,6-dimethylpyridine; triethylsilane; tetrachloromethane; manganese(IV) oxide; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; tris-(o-tolyl)phosphine; sodium iodide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 5: Dess-Martin oxidation / 12: Stille coupling;
DOI:10.1021/ol0527678

Reference yield:

: 878131-83-0
4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-carbaldehyde

: 878132-07-1
(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-2-((1Z,3E)-2-methyl-hepta-1,3,6-trienyl)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / NaI; DBU / tetrahydrofuran / 1.75 h / -78 - 0 °C

2: 98 percent / DIBALH / CH₂Cl₂; hexane / 0.17 h / -78 °C

3: 99 percent / MnO₂ / CH₂Cl₂; benzene / 24 h / 20 °C

4: 94 percent / toluene / 43 h / 130 °C

5: 96 percent / DIBALH / CH₂Cl₂; hexane / 1.5 h / -78 °C

6: 100 percent / PPH₃; CCl₄ / CH₂Cl₂ / 0.5 h / 70 °C

7: 90 percent / (o-tolyl)3P / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 37 h / 50 °C

With tetrachloromethane; manganese(IV) oxide; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; tris-(o-tolyl)phosphine; sodium iodide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; hexane; dichloromethane; toluene; benzene; 7: Stille coupling;
DOI:10.1021/ol0527678