2,3,4,6-Tetra-O-acetyl-a-D-mannopyranose is a phosphorylated glycolipid that inhibits the activity of transferases and endoplasmic reticulum enzymes. This compound has been shown to inhibit the activity of mannosyltransferase and glycosyltransferase in the endoplasmic reticulum. This inhibition may be due to steric hindrance by the acetyl group. The diastereoselectivity of this compound is also notable. It is one of a few compounds that have shown to be chiral phosphoramidites, which are used in the synthesis of DNA.
CAS Number | 22860-22-6 |
Product Name | 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranose |
IUPAC Name | [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-hydroxyoxan-2-yl]methyl acetate |
Molecular Formula | C14H20O10 |
Molecular Weight | 348.303 |
InChI | InChI=1S/C14H20O10/c1-6(15)20-5-10-11(21-7(2)16)12(22-8(3)17)13(14(19)24-10)23-9(4)18/h10-14,19H,5H2,1-4H3/t10-,11-,12+,13+,14+/m1/s1 |
InChI Key | IEOLRPPTIGNUNP-DGTMBMJNSA-N |
SMILES | CC(=O)OCC1C(C(C(C(O1)O)OC(=O)C)OC(=O)C)OC(=O)C |
CAS No: 22860-22-6 MDL No: MFCD08274522 Chemical Formula: C14H20O10 Molecular Weight: 348.303 |
References: 1. Mikamo M, et.al.,, Carbohyd. Res., 1989, 191, p150 |