Phosphono-sugars

Dimethyl phosphite has been added to glycosulose derivatives (for example, 218) as a means of preparing C-phosphono sugars.474 Methyl 2,3,6-tri-0-benzoyl-a-D-n 6o-hexopyranosid-4-ulose reacts with 1,2-ethanedithiol to form the corresponding 4,4-ethylene dithioacetal.475... 

Scheme 63 Preparation of phosphono sugars 200 from allyl allylphosphonates 198...

Phosphono sugars, (2R,4R,5R)- and (2S,4J ,5J )-4,5-dimethoxy-2-oxo-2-phenyl-l,2-oxaphosphorinates (211A and 211B), are prepared from 1,4-dibromo-l,4-dideoxy-2,3-di-0-methyl-L-threitol (209), being prepared from... 

Inorganic Derivatives >- The racemic phosphono-sugar derivative (34). "... 

Sulfation of the sugar moieties of chondroitins occurs by a sequence of steps, the first of which involves formation of 3 -0-phosphono-5 -adenylyl hydrogen sulfate, the sulfate donor.346,347 This enzyme is present in a number of the tissues in which these glycoproteins... 

Formation of a new stereogenic carbon center during the addition of a dialkyl phosphite to the C - C double bond of a sugar system usually proceeds with high stereoselectivity. For example, methyl 4,6-0-benzylidcnc-2,3-dideoxy-3-nitro-/ -D-criv/ ro-hex-2-cnopyranosidc reacts with dialkyl phosphites in the presence of catalytic amounts of triethylumine to give preferentially the 3-nitro-2-phosphono- /wo derivatives 1714. 

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