272106-60-2

Upstream product

• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 272106-58-8 ((4aR,8R,8aS)-7-Benzyloxy-8-hydroxy-2,2-dimethyl-4a,7,8,8a-tetrahydro-4H-1,3-dioxa-5,7-diaza-naphthalen-6-yl)-carbamic acid benzyl ester 
• 272106-56-6 C₃₉H₄₇N₃O₆Si 
• 272106-57-7 C₂₃H₂₉N₃O₆ 
• 187972-12-9 1-benzyloxy-3-benzyloxycarbonylthiourea 

Downstream Products

• 272106-61-3 (4aR,8R,8aS)-6-Amino-2,2-dimethyl-4,4a,8,8a-tetrahydro-1,3-dioxa-5,7-diaza-naphthalene-7,8-diol 

Relevant academic research and scientific papers

Synthesis of 2-Substituted Polyhydroxytetrahydropyrimidines (N-Hydroxy Cyclic Guanidino-Sugars): Transition-State Mimics of Enzymatic Glycosidic Cleavage

The synthesis of 2-substituted polyhydroxytetrahydropyrimidines as transition-state mimics of enzymatic glycosidic cleavage has been achieved by using guanylation and cyclization methodologies. The D-galacto type N-hydroxy cyclic guanidino-sugar 21 was synthesized in six steps from amine 7 and thiourea 14 in an overall yield of 59%. To further derivatize compound 21 to incorporate the leaving group moiety, we have synthesized 2-methylsulfanyl compounds 26-29 as key intermediates. The 2-methylsulfanyl group in 29 was displaced with amines, assisted by silver tetrafluoroborate as Lewis acid, to give protected cyclic guanidines 30-32 in moderate yields (60-67%). Removal of the protecting groups in 32 gave the D-galacto-type N-hydroxy cyclic guanidino-sugar 34. The key steps in the synthesis of the 6-deoxy-DL-galacto type N-hydroxy cyclic guanidino-sugars 49, 54, and 64-66 involve cyclization of the appropriate acetal intermediates (45, 50, and 58-60) followed by removal of the protecting groups.