(3R,4S,7S,8R)-3-benzyloxy-1-(t-butyldimethylsiloxy)-7,9-[(R)-p-methoxybenzylidenedioxy]-4,8-dimethyl-cis-5-nonene

Base Information

• Chemical Name: (3R,4S,7S,8R)-3-benzyloxy-1-(t-butyldimethylsiloxy)-7,9-[(R)-p-methoxybenzylidenedioxy]-4,8-dimethyl-cis-5-nonene
• CAS No.: 668421-77-0
• Molecular Formula: C₃₂H₄₈O₅Si
• Molecular Weight: 540.816
• Mol file: 668421-77-0.mol

Synonyms:(3R,4S,7S,8R)-3-benzyloxy-1-(t-butyldimethylsiloxy)-7,9-[(R)-p-methoxybenzylidenedioxy]-4,8-dimethyl-cis-5-nonene

Chemical Property of (3R,4S,7S,8R)-3-benzyloxy-1-(t-butyldimethylsiloxy)-7,9-[(R)-p-methoxybenzylidenedioxy]-4,8-dimethyl-cis-5-nonene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,7S,8R)-3-benzyloxy-1-(t-butyldimethylsiloxy)-7,9-[(R)-p-methoxybenzylidenedioxy]-4,8-dimethyl-cis-5-nonene

There total 21 articles about (3R,4S,7S,8R)-3-benzyloxy-1-(t-butyldimethylsiloxy)-7,9-[(R)-p-methoxybenzylidenedioxy]-4,8-dimethyl-cis-5-nonene 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: 80.0%

(2R,4R,5R)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane-4-carbaldehyde (668421-70-3) + [(2R,3R)-3-benzyloxy-5-(tert-butyldimethylsiloxy)-2-methylpentyl]triphenylphosphonium iodide → (3R,4S,7S,8R)-3-benzyloxy-1-(t-butyldimethylsiloxy)-7,9-[(R)-p-methoxybenzylidenedioxy]-4,8-dimethyl-cis-5-nonene (668421-77-0)

Guidance literature:

With sodium hexamethyldisilazane; In toluene; at -78 - 20 ℃;

DOI:10.1016/j.tetlet.2003.10.213

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (3R,4S,7S,8R)-3-benzyloxy-1-(t-butyldimethylsiloxy)-7,9-[(R)-p-methoxybenzylidenedioxy]-4,8-dimethyl-cis-5-nonene (668421-77-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: CSA / CH₂Cl₂ / 2 h / 20 °C

2.1: TBAF / tetrahydrofuran / 1 h / 0 °C

3.1: NCS; K₂CO₃; N-t-butylbenzenesulfenamide / 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

4.1: NaHMDS / toluene / 0.08 h / 20 °C

4.2: toluene / 1 h / 20 °C

With N-chloro-succinimide; N-(phenylthio)-N-(tert-butyl)amine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium carbonate; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/chem.200500417

Reference yield:

[(2R,4R,5R)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]methanol (861695-51-4) → (3R,4S,7S,8R)-3-benzyloxy-1-(t-butyldimethylsiloxy)-7,9-[(R)-p-methoxybenzylidenedioxy]-4,8-dimethyl-cis-5-nonene (668421-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NCS; K₂CO₃; N-t-butylbenzenesulfenamide / 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

2.1: NaHMDS / toluene / 0.08 h / 20 °C

2.2: toluene / 1 h / 20 °C

With N-chloro-succinimide; N-(phenylthio)-N-(tert-butyl)amine; sodium hexamethyldisilazane; potassium carbonate; 4 A molecular sieve; In dichloromethane; toluene;

DOI:10.1002/chem.200500417

upstream raw materials:

(2R,4R,5R)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane-4-carbaldehyde

(2S,3R)-1,3-[(S)-benzylidenedioxy]-5-(t-butyldimethylsiloxy)-2-methylpentane

(2S,3R)-3-benzyloxy-5-(t-butyldimethylsiloxy)-2-methylpentanol

(2R,3R)-1-(triisopropylsiloxy)-2,4-[(R)-p-methoxybenzylidenedioxy]-3-methylbutane

Downstream raw materials:

(2R,3S,6S,7R)-7-benzyloxy-9-(t-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,6-dimethyl-cis-4-nonen-1-ol

(3R,4S,7S,8R)-3-benzyloxy-9-oxo-4,8-dimethylnonan-7-olide

(3S,4S,7S,8R)-3-benzyloxy-9-hydroxy-4,8-dimethylnonan-7-olide

(3R,4S,7S,8R)-3-benzyloxy-9-(tert-butyldiphenylsiloxy)-4,8-dimethylnonan-7-olide