119756-56-8

Basic information

• Product Name: (1R,2R,3R,4R)-3-Amino-4-(tetrahydro-pyran-2-yloxy)-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid methyl ester
• CAS NO: 119756-56-8
• Molecular Weight: 281.352
• Mol File: 119756-56-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,2R,3R,4R)-3-Amino-4-(tetrahydro-pyran-2-yloxy)-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,3R,4R)-3-Amino-4-(tetrahydro-pyran-2-yloxy)-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid methyl ester(119756-56-8)
• EPA Substance Registry System: (1R,2R,3R,4R)-3-Amino-4-(tetrahydro-pyran-2-yloxy)-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid methyl ester(119756-56-8)

Safety Data

• Hazardous Substances Data: 119756-56-8(Hazardous Substances Data)

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 119756-54-6 1-(2'-tetrahydropyranyloxy)cyclohexa-1,4-diene 
• 119756-31-9 1-(2'-tetrahydropyranyloxy)cyclohexa-1,3-diene 
• 4203-50-3 2-phenoxytetrahydropyran 
• 119756-32-0 5-exo-methoxycarbonyl-6-endo-nitro-1-(2'-tetrahydropyranyloxy)bicyclo<2.2.2>oct-2-ene 

Relevant articles and documents

AN APPROACH TO THE SYNTHESIS OF GELSEMINE: THE INTRAMOLECULAR RAECTION OF AN ALLYLSILANE WITH AN ACYLIMINIUM ION FOR THE SYNTHESIS OF ONE OF THE QUATERNARY CENTRES

We describe an efficient synthesis (summarised in Schemes 8 and 10) of an advanced intermediate (34) suitable for the synthesis of gelsemine.The key steps in the synthesis are (i) the Diels-Alder reaction between 1-tetrahydropyranyloxycyclohexa-1,3-diene (10) and methyl β-nitroacrylate (11) giving an adduct (12), in which the chiral centre in the tetrahydropyranyl ring is produced substantially in only one sense, (ii) the rearrangement of a bicyclooctane (23) into a bicyclooctane (24), where control of which bridge migrates is achieved by a choice of the counterion in the Lewis acid, and (iii) the efficient formation of the quaternary centre by an intramolecular reaction between an allylsilane group and an acyliminium ion (33 -> 34).