64951-98-0Relevant academic research and scientific papers
Deleterious effect of 7-methyl group on glycosylation of 2-naphthols
Mitra, Prithiba,Mandal, Subhajit,Chakraborty, Soumen,Mal, Dipakranjan
, p. 5610 - 5619 (2015/08/03)
C-Glycosylations of several 2-naphthols with different glycosyl donors have been investigated in the pursuit of the total synthesis of mayamycin (1). While glycosylations of the parent 2-naphthol are readily achievable, those of 5-methoxy-7-methyl-2-napht
The Synthesis of Some Pyrrolidines as Potential Precursors to Retronecine
Ferro, Vito,Skelton, Brian W.,Stick, Robert V.,White, Allan H.
, p. 787 - 803 (2007/10/02)
Methyl β-D-galactopyranoside was converted into methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside, but subsequent transformation of the anomeric centre into a dithioacetal was unsatisfactory. Alternatively, methyl β-D-galactopyranoside easily gave methyl 4-azido-3,6-di-O-benzyl-2,4-dideoxy-β-D-arabino-hexoside, and this could be transformed by a reductive amination into two pyrrolidines as potential precursors to retronecine. Related chemistry gave (4S,5S,6R)-6-benzyloxy-4-benzyloxymethyl-3-oxa-1-azabicyclooctan-2-one, the structure of which was confirmed by a single-crystal X-ray structure determination. Finally, the synthesis of a potential precursor to heliotridine (an epimer of retronecine), namely methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-α-D-ribo-hexoside, from methyl α-D-mannopyranoside is reported.
Synthesis and Utilization of the Chiral Synthon Methyl 3-O-Benzyl-2,4,6-trideoxy-6-iodo-α-D-erythro-hexopyranoside in the Synthesis of a Potent HMG-CoA Reductase Inhibitor
Prugh, John D.,Rooney, C. Stanley,Deana, Albert A.,Ramjit, Harri G.
, p. 648 - 657 (2007/10/02)
Synthesis of the potent HMG-CoA reductase inhibitor 1a has been achieved by utilizing the chiral synthon 2, which was prepared from methyl α-D-glucopyranoside in 12 steps (6 new).A key step in this sequence, which should have general applicability for the
PROCESS FOR PREPARING INHIBITORS OF 3-HYDROXY-3-METHYLGLUTARYL COENZYME A REDUCTASE VIA A CHIRAL SYNTHON
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, (2008/06/13)
Totally synthetic analogs of the known inhibitors of 3-hydroxy-3-methylglutaryl coenzyme A reductase, compactin and mevinolin, are prepared from a chiral synthon derived from D-glucose which has the same chirality as the natural products.
