1,6-Anhydro-2,3,4-tri-O-benzyl-Beta-D-glucopyranose
Product Code
TRC-A658750
CAS Number
Product Format
Neat
Molecular Formula
C27 H28 O5
Molecular Weight
432.51
Product Categories
TRC, Macrolides, Pharmaceutical Toxicology Reference Materials
Product Information
Chemical Data
Analyte Name
1,6-Anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose
CAS Number
10548-46-6
Molecular Formula
C27 H28 O5
Molecular Weight
432.51
Accurate Mass
432.1937
SMILES
C(O[C@@H]1[C@H]2CO[C@H](O2)[C@H](OCc3ccccc3)[C@H]1OCc4ccccc4)c5ccccc5
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
IUPAC
(1R,2R,3S,4R,5R)-2,3,4-tris(phenylmethoxy)-6,8-dioxabicyclo[3.2.1]octane
Product Data
Storage Temperature
-20°C
Shipping Temperature
Room Temperature
Country of Origin
CANADA
Product Format
Neat
Product Description
1,6-Anhydrohexopyranoses have proven to be valuable synthons for the preparation of biologically important and structurally diverse products (e.g. rifamycin S, indanomycin, thromboxane B2, (+)-biotin, tetrodotoxin, quinone, and macrolide antibiotics) as well as for modified sugars.
References: Fraser-Reid, B., et al. J. Am. Chem. Soc. 106, 731 (1984); Edwards, M.P., et al. J. Org. Chem. 49, 3503 (1984); Kelly, A.G., and Roberts, J.S. J. Chem. Soc., Chem. Commun. 228, (1980); Ogawa, T., et al. Carbohydr. Res. 57, C31 (1977); Isobe, M., et al. Tetrahedron Lett. 28, 6485 (1987); Fresnos, J.N. and Swenton, J.S. , J. Chem. Soc., Chem. Commun. 658, (1985); Kochetkov, N.K. et al., Tetrahedron Lett. 22, 4315, 4319 (1981); Georges, M. et al., Carbohydr. Res. 130, 115 (1984); Paulsen, et al., Chem. Ber. 114, 322 (1981).
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