53399-75-0

Basic information

• Product Name: 2β-acetoxy-4a,7-dihydroxy-1β-methyl-8-methylene-4aα,7β-gibbane-1α,10β-dicarboxylic acid-1=>4a lactone-10-methyl ester
• Synonyms: 2β-acetoxy-4a,7-dihydroxy-1β-methyl-8-methylene-4aα,7β-gibbane-1α,10β-dicarboxylic acid-1=>4a lactone-10-methyl ester
• CAS NO: 53399-75-0
• Molecular Weight: 404.46
• Mol File: 53399-75-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2β-acetoxy-4a,7-dihydroxy-1β-methyl-8-methylene-4aα,7β-gibbane-1α,10β-dicarboxylic acid-1=>4a lactone-10-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2β-acetoxy-4a,7-dihydroxy-1β-methyl-8-methylene-4aα,7β-gibbane-1α,10β-dicarboxylic acid-1=>4a lactone-10-methyl ester(53399-75-0)
• EPA Substance Registry System: 2β-acetoxy-4a,7-dihydroxy-1β-methyl-8-methylene-4aα,7β-gibbane-1α,10β-dicarboxylic acid-1=>4a lactone-10-methyl ester(53399-75-0)

Safety Data

• Hazardous Substances Data: 53399-75-0(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 4747-53-9 gibberellin A₁ methyl ester 
• 151670-90-5 ent-3α-acetoxy-10β-hydroxy-13-methylsulfonyloxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone 

Downstream Products

• 2074-29-5 gibberellin A₄ methyl ester 
• 198990-71-5 ent-3α-acetoxy-10β-hydroxy-13-toluene-p-sulfonyloxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone 
• 198990-72-6 ent-3α-acetoxy-10β-hydroxy-13-phenylsulfonyloxy-20-norgibberell-16-ene-7,19-dioic acid 7-methyl ester 19,10-lactone 

Relevant articles and documents

Displacement of bridgehead sulfonate esters with organometallic reagents: Synthesis of 13-alkylated gibberellins

Gibberellin A3 is converted to 13-methyl GA4 in nine steps and 58% overall yield. A key step in the synthesis is the substitution of a bridgehead sulfonate ester by an alkyl group. A series of organometallic reagents have been investigated to effect this transformation; optimal yields are obtained from reaction of a methanesulfonate with a Gilman-type organocuprate in diethyl ether, in the presence of boron trifluoride-diethyl ether, thus enabling a variety of bridgehead substituents to be introduced in good to excellent yield.