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The Synthesis of 3-Amino-2,3,6-trideoxy-l-xylo-hexopyranose Derivatives by Tak-Ming Cheung; Derek Horton; Roderick J. Sorenson; Wolfgang Weckerle is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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## Derivatives (the 3-acetamido4benzoate 12, the 3-acetamido4acetat.e 13, and the N-ace@ derivative 14) of the methyl giycoside of the title sugar were prepared in a sequence of high-yielding steps from methyl 3-azido-4,6-O-benzyhdene-2,3-d& deoxy-a-D-arabino-hexopyranoside (4). N-Bromosuccinimide converted 4 into the crystalline 4-0-benzoyl-6-bromide 5, which was treated with silver fluoride to afford the 5,6unsaturated glycoside 6. Catalytic hydrogenation of 6 led, essentially, to a 7: 1 mixture of 12 and its 5-epimeric D-arabino isomer 7. Alternatively, 6 was debenzoylated to 10, and the latter treated with lithium ahuninum hydride to give crystahine methyl 3-amino-2,3,6-trideoxy-cr-D-threo-hex-5-enopyranoside (11). Reduction of 11 (as its sah) by hydrogen, with subsequent N-acetylation, furnished the methyl /I-L-xylo-glycoside 13 almost exclusively, with net inversion at C-5. Compouud 13 was readily converted into the crystalhne target compound 14. When dehydrobromination by silver fluoride was attempted with the 3-acetatnido analog (2) of 5, a 3,6-anhydro product (1) was obtained, instead of the expected 5,fkIkene 3.

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Author

Tak-Ming Cheung; Derek Horton; Roderick J. Sorenson; Wolfgang Weckerle

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1978

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)