100806-53-9

Basic information

• Product Name: 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-D-xylitol
• Synonyms: 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-D-xylitol
• CAS NO: 100806-53-9
• Molecular Weight: 578.705
• Mol File: 100806-53-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-D-xylitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-D-xylitol(100806-53-9)
• EPA Substance Registry System: 1,4-di-O-methanesulfonyl-2,3,5-tri-O-benzyl-D-xylitol(100806-53-9)

Safety Data

• Hazardous Substances Data: 100806-53-9(Hazardous Substances Data)

Upstream product

• 87-72-9 D-Xylose 
• 1824-96-0 methyl xylofuranoside 
• 163396-30-3 2’,3’,5’-O-tribenzyl-D-xylonic acid-1’,4’-lactone 
• 16838-89-4 2,3,5-tri-O-benzyl-D-xylofuranose 
• 892858-75-2 methyl 2-O-benzyl-D-xylofuranoside 
• 51755-00-1 methyl 3-O-benzyl-3,5-O-isopropylidene-α-D-xylofuranoside 
• 7045-40-1 Methyl 3,5-O-Isopropylidene-α-D-xylofuranoside 
• 1824-96-0 methyl α-D-xylofuranoside 
• 79083-40-2 2,3,5-tri-O-benzyl-1-O-methyl-α-D-xylofuranoside 
• 100-39-0 benzyl bromide 
• 197716-38-4 2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside 
• 100896-16-0 2,3,5-tri-O-benzyl-D-xylitol 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 100806-54-0 1-azido-1-deoxy-4-O-methanesulphonyl-2,3,5-tri-O-benzyl-D-xylitol 
• 918419-38-2 C₂₉H₃₃NO₃ 
• 126264-87-7 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-imino-N-benzyl-L-arabinitol 
• 6741-71-5 1-(4-thio-α-L-arabino-furanosyl)thymine 
• 6741-71-5 1-(4-thio-β-L-arabino-furanosyl)thymine 
• 208755-45-7 1-(2,3,5-tri-O-benzyl-4-thio-L-arabino-furanosyl)thimine 
• 208755-44-6 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-α,β-L-arabinofuranose 
• 208755-43-5 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-L-arabinitol 

Relevant articles and documents

Synthesis of L-enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides

L-Enantiomers of 4'-thioarabinofuranosyl pyrimidine nucleosides were synthesized from D-xylose. Methyl 2,3,5-tri-O-benzyl-D-xylofuranoside 6 was converted to the corresponding xylitol 7, which was treated with MsCl and then Na2S to give 1,4-anhydro-L-4-thioarabitol 8. As previously reported, Pummerer rearrangement of 8 followed by glycosylation with a silylated thymine and N4-acetylcytosine derivative and deprotection gave the corresponding α- and β-L-4'-thioarabinofuranosyl pyrimidine nucleosides.

GLYCOSIDASE INHIBITORS AND METHODS OF SYNTHESIZING SAME

The compounds of the present invention relate to chain-extended and chain-modified analogues of salacinol, including embodiments where the sulfate moiety has been substituted with a carboxylate or phosphate moiety. In other embodiments the sulfate moiety has been shifted by one carbon atom in the zwitterionic structure. In another embodiment the polyhydroxylated side chain may be replaced with a lipophilic alkyl chain and a suitable counterion. The invention also encompasses methods for synthesizing the salacinol analogues and using the analogues for enzyme inhibition applications.

POTENT COMPETITIVE INHIBITION OF &α-GALACTOSIDASE AND &α-GLUCOSIDASE ACTIVITY BY 1,4-DIDEOXY-1,4-IMINOPENTITOLS: SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL AND OF BOTH ENANTIOMERS OF 1,4-DIDEOXY-1,4-IMINOARABINITOL

The syntheses of 1,4-dideoxy-1,4-imino-D-lyxitol (3), 1,4-dideoxy-1,4-imino-D-arabinitol (4) and 1,4-dideoxy-1,4-imino-L-arabinitol (5) are reported; (3) is a potent competitive inhibitor of α-galactosidase (green coffee beans) and (4) a competitive inhibitor of α-glucosidase (Brewer's yeast) suggesting that iminopentitols have considerable potential as glycosidase inhibitors. (4) was found to be identical to an alkaloid recently isolated from Angylocalyx boutiqueanus.