Glucoside methyl 2- 2-deoxy-6-0-tosyl

A solution of silver nitrate in acetonitrile converts co-deoxy-oj-iodo-aldo.se derivatives to the corresponding w-nitrates without20 123 260 occurrence of desulfonylation. Thus, methyl 2,3-di-0-acetyl-6-deoxy-6-iodo-4-0-tosyl-/3-D-glucoside gave20 an 89% yield of the 6-nitrate after boiling for 2 hours. Boiling for 4 hours was required for preparation of methyl 2,3,4-... 

Of incidental interest is the observation that an w-chlorine atom may be replaced by iodine under Oldham and Rutherford s conditions, without affecting secondary sulfonyloxy groups. Thus, Levene and Tipson107 found that 5-chloro-5-deoxy-2,3-di-0-tosyl-uridine affords the corresponding 5-deoxy-5-iodo derivative plus sodium chloride on the other hand, methyl 4-chloro-4-deoxy-2,3,6-tri-0-tosyl-a-D- glucoside gives117 the 4-chloro-4,6-dideoxy-6-iodo derivative. These observations, taken... 

An unusual reaction occurs116 when methyl 2-(benzyloxycarbonylamino)-2-deoxy-6-0-tosyl-a-D-glucoside (XL) is treated with aqueous, ethanolic alkali solution. The product is methyl 2-amino-3,6-anhydro-2-IV, 4-0-car-bonyl-2-deoxy-a-D-glucoside (XLI). It appears that 3,6-anhydro ring-for-... 

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