1012331-11-1

Basic information

• Product Name: benzyl 2,6-di-O-benzyl-β-L-arabino-hexofuranosid-5-ulose
• Synonyms: benzyl 2,6-di-O-benzyl-β-L-arabino-hexofuranosid-5-ulose
• CAS NO: 1012331-11-1
• Molecular Weight: 448.516
• Mol File: 1012331-11-1.mol

Chemical Properties

• CAS DataBase Reference: benzyl 2,6-di-O-benzyl-β-L-arabino-hexofuranosid-5-ulose(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 2,6-di-O-benzyl-β-L-arabino-hexofuranosid-5-ulose(1012331-11-1)
• EPA Substance Registry System: benzyl 2,6-di-O-benzyl-β-L-arabino-hexofuranosid-5-ulose(1012331-11-1)

Safety Data

• Hazardous Substances Data: 1012331-11-1(Hazardous Substances Data)

Upstream product

• 134039-10-4 (5R)-2,6-di-O-benzyl-5-C-benzyloxy-α-L-arabino-hexopyranoside 
• 100-51-6 benzyl alcohol 

Relevant articles and documents

1-Deoxygalactonojirimycin-lysine hybrids as potent d-galactosidase inhibitors

Cyclization by double reductive amination of l-arabino-hexos-5-ulose with suitably protected d- as well as l-lysine derivatives provided 1-deoxygalactonojirimycin lysine hybrids without any observable epimer formation at C-5. Modifications on the lysine m

Iminosugar glycoconjugates

The iminosugar conjugates according to the invention are N-alkylated 1,5-dideoxy-1,5-iminohexitol or 1,5-dideoxy-1,5-iminopentitol derivatives. The iminosugar component can be, for example, D-gluco-, L-ido-, D-galacto-, D-manno-, 2-acetamido-2-deoxy-D-gluco- or xylo-configuration. The N-substituent is a protected L-α-aminoacid derivative, showing L-lysine-like structural features. The linkage between the carbohydrate and the peptide component is not via the usual glycosidic position, but shows structural features of a very stable tertiary amine. Thus the linkage is very stable. These new compounds are synthesised by using catalytic intramolecular reductive amination of dicarbonyl sugars with partially protected amino acids. The process of intramolecular reductive amination itself is carried out using Pearlman's catalyst (Pd(OH)2/C) and H2 at ambient pressure and room temperature. The resulting accessible class of iminosugar conjugate compounds is represented by the general structure shown in Figure 4(c). The alkyl chain length parameter n can be freely chosen from n=0 upwards. Preferably n is between 0 and 10, and more preferably n is 2, 3, or 4. Residue R1 can be chosen from H, OH, or NHAc, with Ac being Acetyl. R2 can be H, OH, or NHAc. R3, R4, R5, R6 can be H or OH. R7 and R8 can be H, CH2OH CH3, COQH, or COOR with R being Alkyl or Aryl. R9 and R10 can be chosen from H, NH2, NHR, with R being a protective group, an amino acid, a peptide, or a protein. R11 can be OH, O-Alkyl, O-Aryl, NH2, N-Alkyl, N-Aryl, amino acid or peptide, connected via an amide bond.