164024-55-9

Basic information

• Product Name: 1-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose
• Synonyms: 1-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose
• CAS NO: 164024-55-9
• Molecular Weight: 310.347
• Mol File: 164024-55-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose(164024-55-9)
• EPA Substance Registry System: 1-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose(164024-55-9)

Safety Data

• Hazardous Substances Data: 164024-55-9(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 1106973-98-1 C₃₀H₃₃O₇P 
• 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 
• 302788-36-9 (6R)-6-C-allyl-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose 
• 302788-40-5 (1R)-1-C-allyl-N-benzyl-3,6-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 302788-33-6 3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydo-hexos-5-ulo-2,5-furanose 
• 122371-65-7 N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-D-glucitol 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 945394-91-2 2-benzoyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol 
• 945394-89-8 N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol 
• 945394-86-5 6-azido-6-deoxy-1-O-benzyl-α-L-sorbofuranose 
• 945394-84-3 6-azido-6-deoxy-1-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose 

Relevant articles and documents

Synthesis of a mixture of (2S,5R)- and (2S,5S)-2-methyl-1,6-dioxaspiro[4.5]decane, the odor bouquet minor components of Paravespula vulgaris (L.), from L-sorbose

The synthesis of (2S,5RS)-2-methyl-1,6-dioxaspiro[4.5]decane (1) from (2S,4S,5R)- (26) and (2S,4S,5S)-4-hydroxy-2-methyl-1,6-dioxaspiro[4.5]decane (27), obtained in thirteen and fourteen steps from L-sorbose by two convergent syntheses, has been accomplished using Wittig methodology, Barton deoxygenation, reduction, and spiroketalation of the appropriately protected derivatives.

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.