6-chloro-6-deoxy preparation

Some of the rare sugars that have been prepared by way of chloro-deoxy derivatives are 4,6-dideoxy-3-0-methyl-D-xyZo-hexose (D-chal-cose), 3,6-dideoxy-D-n foo-hexose (paratose), 3,6-dideoxy-D-arafcmo-hexose (tyvelose), methyl 2,3-dideoxy-/3-D-glr/cero-hex-2-enopyrano-sid-4-ulose, and certain aminodeoxy sugars. 

Table IV lists most of the sulfates of sugars and their derivatives found in the literature. Where the position of the sulfate group is known with reasonable certainty, this is indicated otherwise, no position is given. Not all of the values of melting points and optical rotations are given for those sulfates that have been prepared a number of times, but the more serious discrepancies have been included. Cyclic sulfates and the chloro-deoxy sulfates, prepared by the action of sulfuryl chloride, have been excluded, since they can be found in a few published papers. ...

The deoxygenation of intact nucleosides has been used to prepare 2- and 3-deoxyguanosine from guanosine via chloro-deoxy sugar intermediates (see also below),5 -deoxy-D-ribo-, -D-arabino-, -D-lyxo-, and -L-lyxo-nucleosides of... 

The 2- and 3-deoxy-D-er> f/i/-o-pentosyl derivatives of 4-amino-5-ethoxy-carbonylimidazole (45) have been prepared from the corresponding ribofuranosyl derivative via l - and 3 -chloro-nucleosides prepared by treatment with O-acetyl-salicyloyl chloride. Scheme 8 shows the reaction of cytosine with thionyl chloride giving 5 -chloro-5 -deoxy-ribo- and -arabino-analogues, which were then... 

Sinclair (92) has described an improved method for the preparation of methyl 6-chloro-6-deoxy- -D-glucopyranoside (137) from methyl a-D-glucopyranoside (11). The reaction was effected with sulfur monochloride S2C12 in N,N-dimethylformamide at room temperature and the... 

Deoxy-5 -fluoroadenosine (911) and the analogs 910, 912, 913 were prepared by coupling of 5-deoxy-5-fluoro-D-ribofuranose and 6-chloro-purine. 2, 5 -Dideoxy-5 -fluoroadenosine (914) was prepared through a displacement reaction of the corresponding 5 -0-tosyl precursor with fluoride (BU4NF in DMF). The carbocyclic nucleosides 915 and 916 have been prepared and their antiviral activities evaluated. 

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