302788-33-6

Basic information

• Product Name: 3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydo-hexos-5-ulo-2,5-furanose
• Synonyms: 3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydo-hexos-5-ulo-2,5-furanose
• CAS NO: 302788-33-6
• Molecular Weight: 398.456
• Mol File: 302788-33-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydo-hexos-5-ulo-2,5-furanose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydo-hexos-5-ulo-2,5-furanose(302788-33-6)
• EPA Substance Registry System: 3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydo-hexos-5-ulo-2,5-furanose(302788-33-6)

Safety Data

• Hazardous Substances Data: 302788-33-6(Hazardous Substances Data)

Upstream product

• 17682-70-1 2,3:4,6-bis-O-isopropylidene-L-sorbose 
• 74342-16-8 1-O-benzyl-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose 
• 100-39-0 benzyl bromide 
• 302788-32-5 1,4-di-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose 
• 164024-55-9 1-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose 

Downstream Products

• 302788-34-7 3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydohexos-5-ulo-2,5-furanose N-benzylimine 
• 858675-36-2 (1R)-3,6-di-O-benzyl-1-C-butyl-N-butyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 858675-34-0 (6R)-1,4-di-O-benzyl-6-butylamino-6-C-butyl-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose 
• 858675-37-3 (1R)-3,6-di-O-benzyl-1-C-octyl-N-octyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 858675-35-1 (6R)-1,4-di-O-benzyl-6-deoxy-2,3-O-isopropylidene-6-C-octyl-6-octylamino-α-L-sorbofuranose 
• 473931-86-1 (6S)-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-6-C-diethylphosphono-α-L-sorbofuranose 
• 473931-76-9 (6R)-1,4-di-O-benzyl-6-benzylamino-6-C-n-butyl-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose 
• 473931-79-2 (6S)-1,4-di-O-benzyl-6-benzylamino-6-C-n-butyl-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose 
• 473931-80-5 (1R)-N-benzyl-3,6-di-O-benzyl-1-C-n-butyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 473931-77-0 (6R)-1,4-di-O-benzyl-6-benzylamino-6-deoxy-6-C-ethyl-2,3-O-isopropylidene-α-L-sorbofuranose 
• 473931-81-6 (2R,3R,4R,5S,6R)-1-Benzyl-4-benzyloxy-2-benzyloxymethyl-6-ethyl-piperidine-3,5-diol 
• 302788-36-9 (6R)-6-C-allyl-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose 
• 302788-35-8 (6R)-1,4-di-O-benzyl-6-benzylamino-6-deoxy-6-C-ethenyl-2,3-O-isopropylidene-α-L-sorbofuranose 
• 302788-37-0 (6S)-1,4-di-O-benzyl-6-benzylamino-6-deoxy-6-C-ethenyl-2,3-O-isopropylidene-α-L-sorbofuranose 

Relevant articles and documents

A general strategy for the practical synthesis of nojirimycin C-glycosides and analogues. Extension to the first reported example of an iminosugar 1-phosphonate

An efficient and versatile strategy for the synthesis of nojirimycin C-glycosides and related compounds with full stereocontrol is reported. The key steps of the process are the addition of organometallic reagents onto an L-sorbose-derived imine (13) followed by an internal reductive amination. The addition step, which controls the α vs β-configuration at the pseudoanomeric center in the final product, is highly diastereoselective (re-face addition), and the stereoselectivity can be effectively inverted by adding an external monodentate Lewis acid (si-face addition). The complete synthesis could be achieved in 10 steps only from commercially available 2,3;4,6-di-O-isopropylidene-C-L-sorbofuranose and provided α or β-1-C-substituted 1-deoxynojirimycin derivatives in 27-52% overall yield. The strategy was successfully extended to the first example of an iminosugar 1-phosphonate. The methodology provides access to a wide range of biologically relevant glycoconjugate mimetics in which the glycosidic function is replaced by an imino-C-glycosidic linkage.