178976-44-8Relevant academic research and scientific papers
Asymmetric syntheses of methyl N, O-diacetyl-d-3-epi-daunosaminide and methyl N, O-diacetyl-d-ristosaminide
Csatayova, Kristina,Davies, Stephen G.,Ford, J. Gair,Lee, James A.,Roberts, Paul M.,Thomson, James E.
, p. 12397 - 12408 (2014/01/17)
Ab initio asymmetric syntheses of methyl N,O-diacetyl-d-3-epi-daunosaminide and methyl N,O-diacetyl-d-ristosaminide, employing diastereoselective epoxidation and dihydroxylation, respectively, of alkyl (3S,αR,Z)-3-[N- benzyl-N-(α-methylbenzyl)amino]hex-4-
Highly diastereoselective and stereodivergent dihydroxylations of acyclic allylic amines: Application to the asymmetric synthesis of 3,6-dideoxy-3-amino- l-talose
Csatayova, Kristina,Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.,Wilson, David L.
supporting information; experimental part, p. 2606 - 2609 (2011/07/08)
Aminohydroxylation of tert-butyl sorbate [tert-butyl (E,E)-hexa-2,4- dienoate] using enantiopure lithium (R)-N-benzyl-N-(α-methylbenzyl)amide and (-)-camphorsulfonyloxaziridine gives tert-butyl (R,R,R,E)-2-hydroxy-3-[N- benzyl-N-(α-methylbenzyl)amino]hex-4-enoate in >99:1 dr. Subsequent dihydroxylation under Upjohn conditions (OsO4/NMO) gives tert-butyl (2R,3R,4S,5S,αR)-2,4,5-trihydroxy-3-[N-benzyl-N-(α-methylbenzyl) amino]hexanoate (in 95:5 dr) while dihydroxylation under Donohoe conditions (OsO4/TMEDA) proceeds with antipodal diastereofacial selectivity to give the (R,R,R,R,R)-diastereoisomer (in 95:5 dr). The amino triols resulting from these dihydroxylation reactions are useful for further elaboration, as demonstrated by the asymmetric synthesis of 3,6-dideoxy-3-amino-l-talose.
Syntheses of derivatives of L-daunosamine and its C-3 epimer employing as the key step the asymmetric conjugate addition of a homochiral lithium amide to tert-butyl (E,E)-hexa-2,4-dienoate
Davies, Stephen G.,Smyth, G. Darren,Chippindale, Ann M.
, p. 3089 - 3104 (2007/10/03)
The highly diastereoselective asymmetric conjugate addition of lithium (R)-N-benzyl-α-methylbenzylamide to methyl or tert-butyl (E,E)-hexa-2,4-dienoate, followed by osmium tetroxide-catalysed dihydroxylation of the resulting adducts, provides a concise ro
Asymmetric synthesis of methyl α-L-daunosaminide hydrochloride
Davies, Stephen G.,Smyth, G. Darren
, p. 1273 - 1274 (2007/10/03)
Methyl α-L-daunosaminide hydrochloride was synthesised in five steps from methyl (E,E)-hexa-2,4-dienoate, via the conjugate addition of (R)-lithium N-benzyl-α-methylbenzylamide, and osmium tetroxide catalysed dihydroxylation of the resulting adduct.
