217324-99-7

Basic information

• Product Name: methyl (methyl-3-O-benzyl-2-O-methoxymethyl-α-D-xylofuranoside) uronate
• Synonyms: methyl (methyl-3-O-benzyl-2-O-methoxymethyl-α-D-xylofuranoside) uronate
• CAS NO: 217324-99-7
• Molecular Weight: 326.346
• Mol File: 217324-99-7.mol

Chemical Properties

• CAS DataBase Reference: methyl (methyl-3-O-benzyl-2-O-methoxymethyl-α-D-xylofuranoside) uronate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (methyl-3-O-benzyl-2-O-methoxymethyl-α-D-xylofuranoside) uronate(217324-99-7)
• EPA Substance Registry System: methyl (methyl-3-O-benzyl-2-O-methoxymethyl-α-D-xylofuranoside) uronate(217324-99-7)

Safety Data

• Hazardous Substances Data: 217324-99-7(Hazardous Substances Data)

Upstream product

• 39682-04-7 (3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 217325-05-8 ((2S,3R,4R,5S)-3-Benzyloxy-2-benzyloxymethyl-5-methoxy-4-methoxymethoxy-tetrahydro-furan-2-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 
• 250584-44-2 (6R)-methyl-3-O-benzyl-2-O-methoxymethyl-4-C-benzyloxymethyl-6,7-O-isopropyl-β-L-altrofuranoside 
• 217325-03-6 (1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane 
• 250584-41-9 (6R)-methyl-3-O-benzyl-2-O-methoxymethyl-4-C-benzyloxymethyl-6,7-O-isopropyl-α-D-galactofuranoside 
• 250584-40-8 (6R)-methyl-3-O-benzyl-2-O-methoxymethyl-4-C-hydroxymethyl-6,7-O-isopropyl-α-D-galacto/α-D-gluco/β-L-altrofuranoside 
• 217325-00-3 methyl (methyl-3-O-benzyl-2-O-methoxymethyl-4-C-(hydroxy-(2,2-dimethyl[1,3]dioxolan-4-yl)methyl)-α-D-xylo/β-L-arabinofuranoside) uronate 

Relevant articles and documents

An approach to the bicyclic core of the zaragozic acids via the aldol reaction between methyl (α-D-xylofuranoside)uronate and D-(R)-glyceraldehyde acetonide

The aldol reaction between methyl (methyl-3-O-benzyl-2-O-methoxymethyl- α-D-xylofurano-side)uronate and D-(R)-glyceraldehyde acetonide, promoted by cerium(III) chloride, led to three diastereoisomers in good yield and high level of stereoselectivity at the newly created quaternary center of the furanoside. Under acidic conditions, the aldol derivatives undergo transketalization to afford different bicyclic ketal isomers. This reaction was used as the key step in the synthesis of a functionalized bicyclic core of the zaragozic acids.

A short synthesis of the bicyclic core of the zaragozic acids

A synthesis of the highly functionalized bicyclic core of the zaragozic acids is described, in which the key step involves the construction of the C4 quaternary carbon center by a CeCl3-promoted aldol reaction between the α- D-xylofuranuronic acid derivative 2 and D-(R)-glyceraldehyde acetonide.