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Catalog Number
ACM3601896
Product Name
1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose
Structure
CAS
3601-89-6
Category
Main Products
Description
The synthesis pathway for the compound '(2R,3S)-5-chloro-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate' involves the protection of the hydroxyl group in the tetrahydrofuran ring, followed by the introduction of the 4-methylbenzoyl group at the C-3 position. The resulting intermediate is then reacted with 4-methylbenzoic acid to form the final product.
What is the molecular formula of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?
The molecular formula is C21H21ClO5.
What is the molecular weight of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?
The molecular weight is 388.8 g/mol.
What is the IUPAC name of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?
The IUPAC name is [(2R,3S,5S)-5-chloro-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate.
What is the InChI of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?
The InChI is InChI=1S/C21H21ClO5/c1-13-3-7-15(8-4-13)20(23)25-12-18-17(11-19(22)26-18)27-21(24)16-9-5-14(2)6-10-16/h3-10,17-19H,11-12H2,1-2H3/t17-,18+,19+/m0/s1.
What is the InChIKey of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?
The InChIKey is FJHSYOMVMMNQJQ-IPMKNSEASA-N.
What is the canonical SMILES of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?
The canonical SMILES is CC1=CC=C(C=C1)C(=O)OCC2C(CC(O2)Cl)OC(=O)C3=CC=C(C=C3)C.
What is the CAS number of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?
The CAS number is 4330-21-6.
What is the EC number of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?
The EC number is 224-367-3.
What is the XLogP3-AA value of 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose?
The XLogP3-AA value is 4.9.
How many hydrogen bond acceptor counts does 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose have?
It has 5 hydrogen bond acceptor counts.
Synthetic Route of DNA Base Analogues via SN2 Reaction at the Anomeric Center of Hoffer's Chlorosugar
Bag S S,et al. Bioorganic & Medicinal Chemistry Letters, 2016, 26(8): 2044-2050.
1-Chloro-2-deoxy-3,5-di-O-toluoyl-a-D-ribofuranoose (also known as Hoffer's chlorosugar) is a synthetic building block used in nucleic acid research that provides a range of α- and β-linked 2 ' -Deoxyribose derivatives. For example, the SN2 substitution reaction at the anomeric center of Hoffer's chlorosugar with various 5-substituted aromatic tetrazoles in THF in presence of K2CO3 proceeds with regioselectivity at N2-tetrazoles and stereoselectivity at α-chlorosugar with very good yield.
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Bag S S,et al. Bioorganic & Medicinal Chemistry Letters, 2016, 26(8): 2044-2050.
