(S)-1-{(S)-[6-(Bis-benzyloxy-methyl)-cyclohexa-1,5-dienyl]-hydroxy-methyl}-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enol

Base Information

• Chemical Name: (S)-1-{(S)-[6-(Bis-benzyloxy-methyl)-cyclohexa-1,5-dienyl]-hydroxy-methyl}-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enol
• CAS No.: 219780-68-4
• Molecular Formula: C₄₇H₆₂O₅SSi
• Molecular Weight: 767.158
• Mol file: 219780-68-4.mol

Synonyms:(S)-1-{(S)-[6-(Bis-benzyloxy-methyl)-cyclohexa-1,5-dienyl]-hydroxy-methyl}-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enol

Chemical Property of (S)-1-{(S)-[6-(Bis-benzyloxy-methyl)-cyclohexa-1,5-dienyl]-hydroxy-methyl}-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-{(S)-[6-(Bis-benzyloxy-methyl)-cyclohexa-1,5-dienyl]-hydroxy-methyl}-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enol

There total 6 articles about (S)-1-{(S)-[6-(Bis-benzyloxy-methyl)-cyclohexa-1,5-dienyl]-hydroxy-methyl}-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enol 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: 68.0%

(S)-1-Hydroxy-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enecarbaldehyde (162084-46-0) + 6-bromocyclohexa-1,5-dienecarbaldehyde dibenzyl acetal (219780-42-4) → (S)-1-{(S)-[6-(Bis-benzyloxy-methyl)-cyclohexa-1,5-dienyl]-hydroxy-methyl}-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enol (219780-68-4)

Guidance literature:

(S)-1-Hydroxy-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enecarbaldehyde; With tert-butylmagnesium chloride; In tetrahydrofuran; at -78 ℃; for 0.5h;

6-bromocyclohexa-1,5-dienecarbaldehyde dibenzyl acetal; With 2,6-di-tert-butylphenol; tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 1h; Further stages.;

DOI:10.1021/ja9939439

Reference yield:

2-bromo-1,6-dihydroxy-2-cyclohexenecarbaldehyde dimethyl acetal → (S)-1-{(S)-[6-(Bis-benzyloxy-methyl)-cyclohexa-1,5-dienyl]-hydroxy-methyl}-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enol (219780-68-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: p-toluenesulfonic acid / benzene / 6 h / Heating

2.1: 12.4 g / dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

3.1: 82 percent Spectr_. / 1,3-dimethyl-2-phenyl-1,3,2-diaza-phospholidine / tetrahydrofuran / 48 h / 20 °C

4.1: t-butylmagnesium chloride / tetrahydrofuran / 0.5 h / -78 °C

4.2: 68 percent / t-butyllithium; 2,6-di-t-butylphenol / tetrahydrofuran; pentane / 1 h / -78 °C

With 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; dmap; tert-butylmagnesium chloride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; benzene; 1.1: transacetalization / 2.1: cyclocondensation / 3.1: olefination / 4.1: Metallation / 4.2: Condensation;

DOI:10.1021/ja9939439

Reference yield:

(1R,2S)-2-(Bis-benzyloxy-methyl)-3-bromo-cyclohex-3-ene-1,2-diol → (S)-1-{(S)-[6-(Bis-benzyloxy-methyl)-cyclohexa-1,5-dienyl]-hydroxy-methyl}-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enol (219780-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 12.4 g / dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

2.1: 82 percent Spectr_. / 1,3-dimethyl-2-phenyl-1,3,2-diaza-phospholidine / tetrahydrofuran / 48 h / 20 °C

3.1: t-butylmagnesium chloride / tetrahydrofuran / 0.5 h / -78 °C

3.2: 68 percent / t-butyllithium; 2,6-di-t-butylphenol / tetrahydrofuran; pentane / 1 h / -78 °C

With 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; dmap; tert-butylmagnesium chloride; In tetrahydrofuran; dichloromethane; 1.1: cyclocondensation / 2.1: olefination / 3.1: Metallation / 3.2: Condensation;

DOI:10.1021/ja9939439

upstream raw materials:

(S)-1-Hydroxy-4,6,6-trimethyl-5-[1-phenylsulfanyl-meth-(E)-ylidene]-3-triisopropylsilanyloxy-cyclohex-3-enecarbaldehyde

6-bromocyclohexa-1,5-dienecarbaldehyde dibenzyl acetal

benzyl alcohol

Downstream raw materials:

2’-TES-7-TROC-taxol

C₄₃H₆₆O₁₁Si₂

C₄₀H₅₃Cl₃O₁₃Si

C₄₁H₆₄O₉Si₂