1528732-01-5

Basic information

• Product Name: C₂₆H₂₉NO₃
• CAS NO: 1528732-01-5
• Molecular Weight: 403.521
• Mol File: 1528732-01-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₂₆H₂₉NO₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₆H₂₉NO₃(1528732-01-5)
• EPA Substance Registry System: C₂₆H₂₉NO₃(1528732-01-5)

Safety Data

• Hazardous Substances Data: 1528732-01-5(Hazardous Substances Data)

Upstream product

• 16054-77-6 3,5-di-O-benzyl-L-xylofuranose 
• 120693-81-4 (3aS,5S,6R,6aS)-6-(benzyloxy)-5-((benzyloxy)dimethyl)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxole 
• 114861-22-2 1,2-O-isopropylidene-α-L-xylofuranose 
• 87-72-9 L-xylopyranose 
• 1528731-97-6 C₃₄H₃₇NO₄ 
• 124-63-0 methanesulfonyl chloride 

Relevant articles and documents

Diastereoselective concise syntheses of the polyhydroxylated alkaloids DMDP and DAB

A diastereoselective concise synthesis of the iminosugars DMDP and DAB is presented starting from l-xylose and affording the two alkaloids in good yields of 35% and 22% over seven and eight steps, respectively. The Petasis borono-Mannich reaction of 3,5-di-O-benzyl-l-xylofuranose with benzylamine and (E)-styrylboronic acid served as the nitrogen-introducing key step furnishing the new C-N bond in an entirely diastereoselective manner. A chemo- and regioselective O-mesylation followed by an intramolecular SN2- cyclisation allowed the formation of the pyrrolidine ring. Ozonolysis of the styryl double bond and subsequent reduction to form the C-5 hydroxymethyl substituent followed by hydrogenolysis of the benzyl protecting groups concluded the DMDP synthesis. Furthermore, an unexpected fragmentation process during the ozonolysis reaction also gave access to the C-5 decarbinolated DMDP derivative DAB.