3,5-Di-O-(p-toluyl)-2-deoxy-D-ribofuranosyl chloride

Key facts

CAS number

4330-21-6

Form

Solid

form

Molecular weight

388.8 Da

Molecular formula

C₂₁H₂₁ClO₅

PubChem

12907234

Nature

Synthetic

Solubility

Soluble in DMSO (slightly).

Biochemical name

(2R,3S)-5-chloro-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Biological description

Ribose analog used as an intermediate for synthesis of deoxynucleotides. Reacts with nucleophilic bases to produce beta-D-ribofuranosyl glycosides.

Canonical smiles

CC1=CC=C(C=C1)C(=O)OCC2C(CC(O2)Cl)OC(=O)C3=CC=C(C=C3)C

Isomeric smiles

CC1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H](CC(O2)Cl)OC(=O)C3=CC=C(C=C3)C

InChi

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

InChiKey

FJHSYOMVMMNQJQ-PAMZHZACSA-N

IUPAC Name

[(2R,3S)-5-chloro-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate