(-)-(1R,2R,3S,4R)-1-[(2',2'-dimethyl-4'-tertbutyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene

Base Information

• Chemical Name: (-)-(1R,2R,3S,4R)-1-[(2',2'-dimethyl-4'-tertbutyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene
• CAS No.: 220564-14-7
• Molecular Formula: C₂₄H₄₀O₉Si
• Molecular Weight: 500.662
• Mol file: 220564-14-7.mol

Synonyms:(-)-(1R,2R,3S,4R)-1-[(2',2'-dimethyl-4'-tertbutyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene

Chemical Property of (-)-(1R,2R,3S,4R)-1-[(2',2'-dimethyl-4'-tertbutyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1R,2R,3S,4R)-1-[(2',2'-dimethyl-4'-tertbutyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene

There total 3 articles about (-)-(1R,2R,3S,4R)-1-[(2',2'-dimethyl-4'-tertbutyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene 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:

(+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol (4381-96-8,6216-24-6,25348-63-4,80226-74-0,109526-05-8,123354-99-4,123355-00-0,123355-01-1,129829-60-3,129829-61-4,133319-96-7,143615-78-5,143615-79-6) + 4-(tert-butyl-dimethylsilyl)oxy-2,2-dimethylbutyric acid (162537-40-8) → (+)-(1S,2R,3R,4S)-1,2,3,4-tetraacetoxy-5-cyclohexene (189389-04-6) + (1S,2S,3R,4S)-1-[(2',2'-dimethyl-4'-tert-butyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene + (-)-(1R,2R,3S,4R)-1-[(2',2'-dimethyl-4'-tertbutyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene (220564-14-7)

Guidance literature:

With sodium hydroxide; (R,R)-1,2-bis[(o-diphenylphosphino)benzoyl]cyclohexane; tetrahexylammonium bromide; bis(η3-allyl-μ-chloropalladium(II)); In dichloromethane; at 20 ℃; for 4h; Title compound not separated from byproducts.;

DOI:10.1002/1521-3765(20010903)7:17<3768::AID-CHEM3768>3.0.CO;2-C

Reference yield:

(+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol (4381-96-8,6216-24-6,25348-63-4,80226-74-0,109526-05-8,123354-99-4,123355-00-0,123355-01-1,129829-60-3,129829-61-4,133319-96-7,143615-78-5,143615-79-6) + 4-(tert-butyl-dimethylsilyl)oxy-2,2-dimethylbutyric acid (162537-40-8) → (-)-(1R,2S,3S,4R)-1,2,3,4-tetraacetoxy-5-cyclohexene (80226-74-0) + (+)-(1S,2R,3R,4S)-1,2,3,4-tetraacetoxy-5-cyclohexene (189389-04-6) + (-)-(1R,2R,3S,4R)-1-[(2',2'-dimethyl-4'-tertbutyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene (220564-14-7) + 4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-butyric acid 5,6-diacetoxy-4-[4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-butyryloxy]-cyclohex-2-enyl ester

Guidance literature:

With sodium hydroxide; bis(η3-allyl-μ-chloropalladium(II)); tetrahexylammonium bromide; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; In dichloromethane; water; Yields of byproduct given;

DOI:10.1016/S0040-4039(98)02274-6

Reference yield:

(+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol (4381-96-8,6216-24-6,25348-63-4,80226-74-0,109526-05-8,123354-99-4,123355-00-0,123355-01-1,129829-60-3,129829-61-4,133319-96-7,143615-78-5,143615-79-6) + 4-(tert-butyl-dimethylsilyl)oxy-2,2-dimethylbutyric acid (162537-40-8) → (-)-(1R,2S,3S,4R)-1,2,3,4-tetraacetoxy-5-cyclohexene (80226-74-0) + (+)-(1S,2R,3R,4S)-1,2,3,4-tetraacetoxy-5-cyclohexene (189389-04-6) + (1S,2S,3R,4S)-1-[(2',2'-dimethyl-4'-tert-butyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene + (-)-(1R,2R,3S,4R)-1-[(2',2'-dimethyl-4'-tertbutyldimethylsilyloxy)butanoyl]oxy-2,3,4-triacetoxy-5-cyclohexene (220564-14-7) + 4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-butyric acid 5,6-diacetoxy-4-[4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-butyryloxy]-cyclohex-2-enyl ester

Guidance literature:

With sodium hydroxide; bis(η3-allyl-μ-chloropalladium(II)); tetrahexylammonium bromide; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; In dichloromethane; water; Product distribution; kinetic resolution;

DOI:10.1016/S0040-4039(98)02274-6

upstream raw materials:

(+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol

4-(tert-butyl-dimethylsilyl)oxy-2,2-dimethylbutyric acid