272106-61-3

Basic information

• Product Name: 4H-1,3-Dioxino[5,4-d]pyrimidin-8-ol, 6-amino-4a,7,8,8a-tetrahydro-7-hydroxy-2,2-dimethyl-, (4aR,8R,8aS)- (9CI)
• Synonyms: 4H-1,3-Dioxino[5,4-d]pyrimidin-8-ol, 6-amino-4a,7,8,8a-tetrahydro-7-hydroxy-2,2-dimethyl-, (4aR,8R,8aS)- (9CI)
• CAS NO: 272106-61-3
• Molecular Formula: C8H15N3O4
• Molecular Weight: 217.2224
• Product Categories: ALCOHOL
• Mol File: 272106-61-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4H-1,3-Dioxino[5,4-d]pyrimidin-8-ol, 6-amino-4a,7,8,8a-tetrahydro-7-hydroxy-2,2-dimethyl-, (4aR,8R,8aS)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1,3-Dioxino[5,4-d]pyrimidin-8-ol, 6-amino-4a,7,8,8a-tetrahydro-7-hydroxy-2,2-dimethyl-, (4aR,8R,8aS)- (9CI)(272106-61-3)
• EPA Substance Registry System: 4H-1,3-Dioxino[5,4-d]pyrimidin-8-ol, 6-amino-4a,7,8,8a-tetrahydro-7-hydroxy-2,2-dimethyl-, (4aR,8R,8aS)- (9CI)(272106-61-3)

Safety Data

• Hazardous Substances Data: 272106-61-3(Hazardous Substances Data)

Upstream product

• 272106-60-2 ((4aR,8R,8aS)-7-Benzyloxy-2,2-dimethyl-8-triethylsilanyloxy-4a,7,8,8a-tetrahydro-4H-1,3-dioxa-5,7-diaza-naphthalen-6-yl)-carbamic acid benzyl ester 
• 272106-56-6 C₃₉H₄₇N₃O₆Si 
• 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 
• 272106-57-7 C₂₃H₂₉N₃O₆ 

Relevant articles and documents

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.