130359-48-7

Basic information

• Product Name: 1,2-O-isopropylidene-3,5-di-O-(3-methoxybenzyl)-α-D-xylofuranose
• CAS NO: 130359-48-7
• Molecular Weight: 430.498
• Mol File: 130359-48-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2-O-isopropylidene-3,5-di-O-(3-methoxybenzyl)-α-D-xylofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-isopropylidene-3,5-di-O-(3-methoxybenzyl)-α-D-xylofuranose(130359-48-7)
• EPA Substance Registry System: 1,2-O-isopropylidene-3,5-di-O-(3-methoxybenzyl)-α-D-xylofuranose(130359-48-7)

Safety Data

• Hazardous Substances Data: 130359-48-7(Hazardous Substances Data)

Upstream product

• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 824-98-6 m-methoxybenzyl chloride 

Downstream Products

• 103173-92-8 (6aS,7S,13bS)-6a,7,9,13b-tetrahydro-7-<(1R)-1-hydroxy-2-<(3-methoxybenzyl)oxy>-ethyl>-3,11-dimethoxy-5H-<2>benzopyrano<3,4-d><2>benzoxepin 
• 130359-65-8 methyl 3,5-di-O-(3-methoxybenzyl)-β-D-xylofuranoside 
• 130359-49-8 methyl 3,5-di-O-(3-methoxybenzyl)-α-D-xylofuranoside 
• 130359-52-3 (3S)-1,3,4,5-tetrahydro-3-<(1R)-1-hydroxy-2-<<3-methoxybenzyl>oxy>-ethyl>-8-methoxy-2-benzoxepin-4-one 
• 130359-53-4 (2S,3R,3aS,4aR,6R,7S,7aR,8aS)-3,7-Bis-(3-methoxy-benzyloxy)-2,6-bis-(3-methoxy-benzyloxymethyl)-octahydro-difuro[2,3-b;2',3'-e][1,4]dioxine 

Relevant articles and documents

Multiple and long-range participation of benzyl groups in intramolecular C-arylation reactions of benzylated glycosides.

The intrinsic reactivity of furanosides bearing activated O-benzyl substituents (3-methoxybenzyl), in the presence of bidentate Lewis acids such as tin(IV) chloride, was explored. These glycosides were found to exhibit extremely interesting chemical properties. Thus, with three reactive substituents (at O-2,3,5), the corresponding glycosides (1 and 7) underwent a novel internal bis-C-arylation process, which involved successive alkylations of the benzyl groups at O-2 and O-3 ("multiple participation"), leading to the formal replacement of the two C-O bonds at the anomeric center of the glycoside by two C-C bonds. The bis-C-arylated constitution of the resulting polycyclic compounds 4 and 8, and the cis configuration of their fused ring system (a tetrahydro-[2]benzopyrano[3,4-d][2]benzoxepin derivative), were determined on the basis of their n.m.r.-spectral parameters. With two 3-methoxybenzyl substituents (at O-3 and O-5, compound 6), intramolecular alkylation of the benzyl group at O-3 or O-5 occurred when glycoside 6 was reacted with titanium(IV) chloride or tin(IV) chloride, respectively, thereby leading to novel bicyclic internal aryl C-glycosides (9 and 12) as major products ("long-range participation"). The constitution of compounds 9 and 12 was unambiguously established by the reactions of analogs of 6 bearing only one 3-methoxybenzyl substituent at a specific position (at O-3: 15; at O-5: 20). The unexpected divergent behavior of 6 in the presence of titanium(IV) and tin(IV) chloride remains to be explained. The availability of compound 9 made it possible to independently prepare the bis-C-arylated derivative 8 (by way of the reverse sequence of internal C-arylation reactions) and thereby to definitively demonstrate its constitution. These unprecedented reactions extend the scope of the intramolecular C-glycosidation of substituted sugars and provide novel methodologies in synthetic carbohydrate chemistry.