956006-07-8

Basic information

• Product Name: ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(iodomethyl)cyclohexyl)methanol
• Synonyms: ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(iodomethyl)cyclohexyl)methanol
• CAS NO: 956006-07-8
• Molecular Weight: 466.359
• Mol File: 956006-07-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(iodomethyl)cyclohexyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(iodomethyl)cyclohexyl)methanol(956006-07-8)
• EPA Substance Registry System: ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(iodomethyl)cyclohexyl)methanol(956006-07-8)

Safety Data

• Hazardous Substances Data: 956006-07-8(Hazardous Substances Data)

Upstream product

• 956006-37-4 ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(iodomethyl)cyclohexylmethoxy)(tert-butyl)dimethylsilane 
• 956006-34-1 (1S,3R,4R,6R)-3-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylate 
• 956006-35-2 (1R,2R,4R,5R)-bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4-(benzyloxy)-5-hydroxycyclohexane-1,2-dicarboxylate 
• 956006-03-4 (1R,2R,4R,5R)-bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4,5-bis(benzyloxy)cyclohexane-1,2-dicarboxylate 
• 73627-88-0 (1R,2R,1'S,2'R,5'S)-cyclohex-4-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester 

Downstream Products

• 956006-11-4 (S)-3-((S)-1-((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(hydroxymethyl)cyclohexyl)-3-(tert-butyldimethylsilyloxy)propan-2-ylamino)-4-benzyloxazolidin-2-one 
• 1365034-52-1 2-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-4-yl)ethyl benzoate 
• 1365034-53-2 2-((3R,4R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-3-yl)ethyl benzoate 
• 207129-36-0 [(2S,4S,5R)-2-hydroxymethyl-5-vinyl-2-quinuclidine] 
• 1312224-56-8 1-((3S,4aR,6R,7R,8aR)-6,7-bis(benzyloxy)-3-((tert-butyldimethylsilyloxy)methyl)octahydroisoquinolin-2-(1H)-yl)-2,2,2-trifluoroethanone 
• 1312224-65-9 N-((S)-1-((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(hydroxymethyl)cyclohexyl)-3-(tert-butyldimethylsilyloxy)propan-2-yl)-2,2,2-trifluoroacetamide 

Relevant articles and documents

Scope of stereoselective Mn-mediated radical addition to chiral hydrazones and application in a formal synthesis of quinine

Stereocontrolled Mn-mediated addition of alkyl iodides to chiral N-acylhydrazones enables strategic C-C bond constructions at the stereogenic centers of chiral amines. Applying this strategy to quinine suggested complementary synthetic approaches to construct C-C bonds attached at the nitrogen-bearing stereogenic center using multifunctional alkyl iodides 6a-d as radical precursors, or using multifunctional chiral N-acylhydrazones 26a-d as radical acceptors. These were included among Mn-mediated radical additions of various alkyl iodides to a range of chiral N-acylhydrazone radical acceptors, leading to the discovery that pyridine and alkene functionalities are incompatible. In a revised strategy, these functionalities are avoided during the Mn-mediated radical addition of 6d to chiral N-acylhydrazone 22b, which generated a key C-C bond with complete stereochemical control at the chiral amine carbon of quinine. Subsequent elaboration included two sequential cyclizations to complete the azabicyclo[2.2.2]octane ring system. Group selectivity between two 2-iodoethyl groups during the second cyclization favored an undesired azabicyclo[3.2.1]octane ring system, an outcome that was found to be consistent with transition state calculations at the B3LYP/6-31G(d) level. Group differentiation at an earlier stage enabled an alternative regioconvergent pathway; this furnished the desired azabicyclo[2.2.2]octane ring system and afforded quincorine (21b), completing a formal synthesis of quinine.