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Sodium cyanoborohydride benzylic compounds

Synthesis from aldonolactones The synthesis of p-homonojirimycin (2) from tetra-(9-benzyl-D-glucono-1,5-lactone (56) (Scheme 8) was achieved by treatment of the latter with (methoxymethoxy)methyl lithium to give the a-D-gluco-heptulose derivative 57, which underwent reduction with LiAlITj to produce a mixture of heptitols 58 (1 1 ratio). Oxidation of 58 using Swern oxidation (DMSO-TFAA) gave the heptodiulose 59. Compound 59 was immediately submitted to reductive amination using ammonium formate in the presence of sodium cyanoborohydride to produce 60 in 50% yield from 58. Removal... [Pg.160]

See other pages where Sodium cyanoborohydride benzylic compounds is mentioned: [Pg.95]    [Pg.1709]    [Pg.281]    [Pg.302]    [Pg.313]    [Pg.336]    [Pg.134]    [Pg.45]    [Pg.446]    [Pg.53]    [Pg.181]    [Pg.81]    [Pg.134]   
See also in sourсe #XX -- [ Pg.969 ]

See also in sourсe #XX -- [ Pg.8 ]

See also in sourсe #XX -- [ Pg.8 ]



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Sodium cyanoborohydride

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