135654-78-3Relevant academic research and scientific papers
Preparation of Some 2-Deoxy- and 2,6-Dideoxy-glycosyl Fluorides
Juenneman, Josef,Lundt, Inge,Thiem, Joachim
, p. 494 - 498 (2007/10/02)
Treatment of 1,3,4,6-tetra-O-acetyl-2-deoxy-D-arabino-hexose (1) and 1,3,4-tri-O-acetyl-2,6-dibromo-2,6-dideoxy-D-glucose (7) with HF*pyridine gave the corresponding α-glycosyl fluorides 2 and 9, respectively, whereas traetment of 3,4,6-tri-O-acetyl-2-deoxy-D-arabino-hexose (4) and of 3,4-di-O-acetyl-2,6-dibromo-2,6-dideoxy-D-glucose (8) with diethylaminosulfur trifluoride (DAST) led to mixtures of the α- and β-fluorides 2 and 5, and 12, respectively.The 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-β-D-glucopyranosyl fluoride (6) was obtained as the only product from treatment of 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-α-D-glucopyranosyl bromide (3) with silver fluoride.Similarly, the 3,4-di-O-acetyl-2,6-dibromo-2,6-dideoxy-α-D-glucopyranosyl bromide (17) gave the corresponding β-fluoride (12) by treatment with silver fluoride.The 3,4-di-O-acetyl-2,6-dibromo-2,6-dideoxy-D-mannopyranosyl derivatives (19, 20, 21) all gave the 3,4-di-O-acetyl-2,6-dibromo-2,6-dideoxy-α-D-mannopyranosyl fluoride (22) by the three methods mentioned.The bromodeoxyglucosyl fluorides 6, 9, 12 and 22 were converted into 2-deoxy- and 2,6-dideoxy-α- or -β-glycosyl fluorides,(5, 11, and 16) by treatment with tributylstannate.Deacetylation of the glycosyl fluorides 9 and 22 gave the deprotected fluorides. 2,6-dibromo-2,6-dideoxy-α-D-gluco- (10) and -D-mannopyranosyl fluoride (23), respectively.Benzylation of the glucosyl fluoride 10 gave the 3,4-di-O-benzylated fluoride 15, whereas the mannosyl fluoride 23 reacted to give the mono-O-benzylated 3,6-anhydro sugar 14 as the only product.
