6-{6-[6-(6-{6-[2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2,4-dimethyl-hex-5-en-3-ol

Base Information

• Chemical Name: 6-{6-[6-(6-{6-[2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2,4-dimethyl-hex-5-en-3-ol
• CAS No.: 375827-05-7
• Molecular Formula: C₄₆H₈₆O₁₁Si
• Molecular Weight: 843.268
• Mol file: 375827-05-7.mol

Synonyms:6-{6-[6-(6-{6-[2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2,4-dimethyl-hex-5-en-3-ol

Chemical Property of 6-{6-[6-(6-{6-[2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2,4-dimethyl-hex-5-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-{6-[6-(6-{6-[2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2,4-dimethyl-hex-5-en-3-ol

There total 1 articles about 6-{6-[6-(6-{6-[2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2,4-dimethyl-hex-5-en-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: 75.0%

C62H96N2O11Si (375827-04-6) → 6-{6-[6-(6-{6-[2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2,4-dimethyl-hex-5-en-3-ol (375827-05-7) + 4-[6-(6-{6-[6-(4-benzyloxy-3,5-dimethyl-hex-1-enyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-(tert-butyl-dimethyl-silanyloxy)-pentan-1-ol

Guidance literature:

With [2,2]bipyridinyl; n-butyllithium; di(tert-butyl)-biphenyl; lithium; In tetrahydrofuran; at -78 ℃; for 0.333333h;

DOI:10.1016/S0040-4020(02)00666-X

Reference yield:

6-{6-[6-(6-{6-[2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2,4-dimethyl-hex-5-en-3-ol (375827-05-7) → dermostatin A (51053-36-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / N-chlorosuccinimide; TEMPO; Bu₄NCl / NaHCO₃; Na₂CO₃ / CH₂Cl₂; H₂O / 2 h / 20 °C / pH 8.6

2: 88 percent / chromous chloride / dioxane; tetrahydrofuran / 3.5 h / 20 °C

3: 100 percent / 4-dimethylaminopyridine; BOP / CH₂Cl₂ / 48 h / 20 °C

4: 77 percent / diisopropylethylamine; triphenylarsine / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 3 h / 20 °C

5: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 20 °C

6: 2.0 mg / LiCl; DBU / acetonitrile / 36 h / 20 °C

7: 77 percent / Dowex 50WX₈-100 acidic resin / methanol / 26 h / 20 - 50 °C

With chromium dichloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; triphenyl-arsane; Dowex 50WX₈-100 acidic resin; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium chloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetonitrile; 1: Einhorn's modified TEMPO oxidation / 4: Stille coupling / 5: Dess-Martin oxidation / 6: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/S0040-4020(02)00666-X

upstream raw materials:

C₆₂H₉₆N₂O₁₁Si

Downstream raw materials:

dermostatin A