1,6-Anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose, commonly referred to as tri-O-benzyl glucal or TBG, is a monosaccharide with the chemical formula C30H28O5. It is a derivative of glucose and belongs to the family of glucals. TBG has been extensively investigated as a building block for the synthesis of biologically relevant compounds and as a potential starting material for the preparation of complex carbohydrates.
| CAS Number | 10548-46-6 |
| Product Name | 1,6-Anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose |
| IUPAC Name | (1R,2R,3S,4R,5R)-2,3,4-tris(phenylmethoxy)-6,8-dioxabicyclo[3.2.1]octane |
| Molecular Formula | C27H28O5 |
| Molecular Weight | 432.51 g/mol |
| InChI | InChI=1S/C27H28O5/c1-4-10-20(11-5-1)16-28-24-23-19-31-27(32-23)26(30-18-22-14-8-3-9-15-22)25(24)29-17-21-12-6-2-7-13-21/h1-15,23-27H,16-19H2/t23-,24-,25+,26-,27-/m1/s1 |
| InChI Key | JSRSLTCFTYHIRT-IURCNINISA-N |
| SMILES | C1C2C(C(C(C(O1)O2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5 |
| Synonyms | 1,6-Anhydro-2,3,4-tris-O-(phenylmethyl)-?-D-glucopyranose; Tri-O-benzyllevoglucosan; |
| Canonical SMILES | C1C2C(C(C(C(O1)O2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5 |
| Isomeric SMILES | C1[C@@H]2[C@H]([C@@H]([C@H]([C@H](O1)O2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5 |
| CAS No: 10548-46-6 MDL No: MFCD02683260 Chemical Formula: C27H28O5 Molecular Weight: 432.51 |
References: 1. Fraser-Reid B, et al., J. Am. Chem. Soc. 1984, 106, p7312. Edwards MP, et al., J. Org. Chem. 1984, 49, p35033. Kochetkov NK, et al., Tetrahedron Lett. 1981, 22, p43154. Georges M, et al., Carbohydr. Res. 1984, 130, p1155. Toshiyuki U, Kenichi H, Kei M, Die Makromolekulare Chemie, 181, 10, p2137 |
| Size | 1 G, 100 MG, 5 G, Other |
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IUPAC:Fuc(a1-2)Gal(b1-3)GlcNAc(b1-3)Gal(b1-4)Glc, G00050MO
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IUPAC:Gal(b1-3)GlcNAc(b1-3)Gal(b1-3)GlcNAc(b1-3)Gal(b1-4)Glc, G62097SF
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