287102-08-3

Basic information

• Product Name: 5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol
• Synonyms: 5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol
• CAS NO: 287102-08-3
• Molecular Weight: 461.558
• Mol File: 287102-08-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol(287102-08-3)
• EPA Substance Registry System: 5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol(287102-08-3)

Safety Data

• Hazardous Substances Data: 287102-08-3(Hazardous Substances Data)

Upstream product

• 287102-05-0 6-deoxy-3,4-O-isopropylidene-5-O-methanesulfonyl-1-O-trityl-D-mannitol 
• 287102-06-1 6-deoxy-3,4-isopropylidene-5-azido-1-O-trityl-D-mannitol 
• 287102-04-9 6-deoxy-3,4-O-isopropylidene-1-O-trityl-D-mannitol 
• 147860-06-8 5-azide-5,6-dideoxy-L-xylo-hexo-2-ulose 
• 84608-23-1 3,4-O-isopropylidene-1-O-trityl-D-mannitol 
• 100-39-0 benzyl bromide 

Downstream Products

• 287102-09-4 1-amino-1-N-benzyloxy-5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-1,2,5,6-tetradeoxy-L-iditol 

Relevant articles and documents

A strategy for the solution-phase parallel synthesis of N- (pyrrolidinylmethyl)hydroxamic acids

Both five- and six-membered iminocyclitols have proven to be useful transition-state analogue inhibitors of glycosidases. They also mimic the transition-state sugar moiety of the nucleoside phosphate sugar in glycosyltransferase-catalyzed reactions. Described here is the development of a general strategy toward the parallel synthesis of a five-membered iminocyclitol linked to a hydroxamic acid group designed to mimic the transition state of GDP-fucose complexed with Mn(II) in fucosyltransferase reactions. The iminocyclitol 8 containing a protected hydroxylamine unit was prepared from D-mannitol. The hydroxamic acid moiety was introduced via the reaction of 8 with various acid chlorides. The strategy is generally applicable to the construction of libraries for identification of glycosyltransferase inhibitors.