1376709-10-2

Basic information

• Product Name: (1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-en-1-yl formate
• Synonyms: (1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-en-1-yl formate
• CAS NO: 1376709-10-2
• Molecular Weight: 228.675
• Mol File: 1376709-10-2.mol

Chemical Properties

• CAS DataBase Reference: (1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-en-1-yl formate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-en-1-yl formate(1376709-10-2)
• EPA Substance Registry System: (1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-en-1-yl formate(1376709-10-2)

Safety Data

• Hazardous Substances Data: 1376709-10-2(Hazardous Substances Data)

Upstream product

• 64-18-6 formic acid 
• 1376709-08-8 (4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone 
• 90129-47-8 (4S,5R)-4-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone 

Downstream Products

• 1376709-28-2 (1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-chloroprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate 
• 1376709-12-4 (1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(3-iodoprop-1-en-2-yl)-3-methylcyclohex-2-en-1-yl formate 
• 1376709-03-3 (4aR,6R,8aR)-6-((tert-butyldimethylsilyl)oxy)-4-(((4-methoxybenzyl)oxy)methyl)-7-methyl-4a,5,6,8a-tetrahydro-2H-chromen-2-one 
• 1376709-27-1 (1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-hydroxy-3-methylcyclohex-2-en-1-yl formate 
• 1376709-22-6 C₃₃H₄₄O₅ 
• 1432620-45-5 (1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-(methoxymethoxy)-3-methylcyclohex-2-en-1-yl formate 
• 1448337-84-5 (1R,4R,6R)-6-(3-iodoprop-1-en-2-yl)-4-(methoxymethoxy)-3-methylcyclohex-2-en-1-yl formate 

Relevant articles and documents

Total synthesis and structure-activity relationship study of the potent cAMP signaling agonist (-)-alotaketal A

A detailed account of the first total synthesis of alotaketal A, a tricyclic spiroketal sesterterpenoid that potently activates the cAMP signaling pathway, is provided. The synthesis employs both intra- and intermolecular reductive allylation of esters for assembling one of the fragments and their coupling. A Hg(OAc)2-mediated allylic mercuration is used to introduce the C22-hydroxyl group. The subtle influence of substituents over the course of the spiroketalization process is revealed. The synthesis confirms the relative and absolute stereochemistry of (-)-alotaketal A and allows verification of alotaketal A's effect over cAMP signaling using reporter-based FRET imaging assays with HEK 293T cells. Our studies also revealed alotaketal A's unique activity in selectively targeting nuclear PKA signaling in living cells. The Royal Society of Chemistry 2013.

Total synthesis of the potent cAMP signaling agonist (-)-Alotaketal A

We have developed a convergent synthetic route to the potent cAMP signaling agonist (-)-alotaketal A that employs two stages of SmI2-mediated reductive allylation reactions for assembling the polycycle and fragment coupling. Also notable are a Hg(OAc)2-mediated selective alkene oxidation and the subtlety of the formation of the unprecedented spiroketal ring system. The probes AKAR4 and ICUE3 were used to evaluate the cAMP singaling agonistic activity of (-)-alotaketal A and elucidate its structure-activity relationship.