954390-26-2

Basic information

• Product Name: tert-butyl (1S,5S)-5-methyl-4-oxocyclohex-2-enyl carbonate
• Synonyms: tert-butyl (1S,5S)-5-methyl-4-oxocyclohex-2-enyl carbonate
• CAS NO: 954390-26-2
• Molecular Weight: 226.273
• Mol File: 954390-26-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: tert-butyl (1S,5S)-5-methyl-4-oxocyclohex-2-enyl carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (1S,5S)-5-methyl-4-oxocyclohex-2-enyl carbonate(954390-26-2)
• EPA Substance Registry System: tert-butyl (1S,5S)-5-methyl-4-oxocyclohex-2-enyl carbonate(954390-26-2)

Safety Data

• Hazardous Substances Data: 954390-26-2(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1043454-50-7 (2S,4S,5R)-4,5-dihydroxy-2-methyl cyclohexanone 

Downstream Products

• 1092513-27-3 tert-butyl (1S,4R,5S)-4-hydroxy-5-methylcyclohex-2-enyl carbonate 
• 1232680-27-1 methyl 2-((1S,5S)-5-methyl-4-oxocyclohex-2-enyloxy)benzoate 
• 1232680-21-5 (4S,6S)-6-methyl-4-phenoxycyclohex-2-enone 
• 1232680-18-0 (4S,6S)-4-benzyloxy-6-methylcyclohex-2-enone 
• 1232680-23-7 (4S,6S)-4-(7-bromo-5,8-dimethoxynaphthalen-1-yloxy)-6-methylcyclohex-2-enone 
• 1232680-28-2 (4S,6S)-4-(4-acetylphenoxy)-6-methylcyclohex-2-enone 
• 1232680-22-6 (4S,6S)-4-(4-methoxyphenoxy)-6-methylcyclohex-2-enone 
• 1232680-24-8 (4S,6S)-6-methyl-4-(o-tolyloxy)cyclohex-2-enone 
• 1232680-25-9 (4S,6S)-4-(2-tert-butylphenoxy)-6-methylcyclohex-2-enone 
• 1232680-26-0 (4S,6S)-4-(4-bromophenoxy)-6-methylcyclohex-2-enone 
• 1232680-30-6 2-((1S,5S)-5-methyl-4-oxocyclohex-2-enyloxy)naphthalene-1,4-dione 
• 1232680-29-3 7-((1S,5S)-5-methyl-4-oxocyclohex-2-enyloxy)-2H-chromen-2-one 
• 1232680-40-8 5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)-3-((1S,5S)-5-methyl-4-oxocyclohex-2-enyloxy)-4H-chromen-4-one 

Relevant articles and documents

Synthesis of O-linked Cyclitol Analogues of Gilvocarcin M and Antibacterial Activity

Two unnatural regioisomeric glycosylated Gilvocarcin analogues were proposed as model compounds to study the origin behind the biosynthetic development of the Gilvocarcins, a class of bioactive C-aryl glycoside natural products. More specifically, the origins behind the proposed O- to C-glycoside migration in the evolution of the biosynthesis for these classes of Angucycline antibiotic natural products. For stability reasons a 5a-carbasugar motif was used to mimic the sugar portion of the molecule and of synthetic ease the proposed abiotic rearrangement move the sugar analogue along with its O-glycoside linkage. The two proposed regioisomeric analogues were synthesized by a regio-divergent synthetic pathway and featured a Mitsunobu-like invertive cyclictolization reaction to install the carbasugar motif. The two regioisomeric Gilvocarcin analogues were evaluated as antibiotic with Gilvocarcin M as a control. Only one of the two isomers showing weak antibiotic activity as compared to Gilvocarcin M.