2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate, CAS No. 122111-01-7

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122111-01-7

Catalog No. EBD46517

CAS 122111-01-7

Name 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

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Basic Information

Synonyms: 2-Deoxy-2,2-difluoro-D-erythropentonicacidgamma-lactone3,5-dibenzoate 2-Deoxy-2,2-difluoro-D-erythro-pentonicacidgamma-lactone3,5-dibenzoate 2-Deoxy-2,2-difuoro-D-Ribofuranofuranose-3,5-dibenzoate 3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-D-erythropentane-1,4-lactone IntermediateofCapecitabine 2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate 2-Deoxy-2,2-difluoropentofuranos-1-ulose-3,5-dibenzoate 2-Deoxy-2,2-difluoro-D-erythro-pentofuranous-1-ulose-3,5-dibenzoate 2-Deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate 4,4-difluoro-5-oxo-2-{[(phenylcarbonyl)oxy]methyl}tetrahydrofuran-3-ylbenzoate(non-preferredname) 2'-Deoxy-2',2',-difluoro-D-erythro-pentofuranous-1-ulose-3,5-dibenzoate 2'-Deoxy-2',2'-difluoro-D-erythro-pentofuranous-1-ulose-3,5-dibenzoate 2-Deoxy-2,2-difluoro-D-erythro-

Molecular Formula: C19H14F2O6

Molecular Weight: 376.31

MDL Number: MFCD04220997

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates

Product Description:

2-Deoxy-2,2-difluoro-D-erythro-pentofuranosyl-1-keto-3,5-dibenzoate is a key sugar-modified nucleoside intermediate. Its structure features a difluorinated ribose moiety with benzoate protecting groups at the 3' and 5' positions, which is crucial for the synthesis of modified nucleoside analogs. This compound is a vital synthetic precursor in the production of Gemcitabine (Gemzar®), a potent chemotherapeutic agent used to treat various cancers, including pancreatic, non-small cell lung, breast, and ovarian cancers. The 2',2'-difluoro modification on the sugar ring is essential for Gemcitabine's mechanism of action, which involves incorporation into DNA to inhibit DNA synthesis and replication, leading to cell death. The benzoate protecting groups in this intermediate facilitate selective chemical transformations during the multi-step synthesis of the final active pharmaceutical ingredient (API). Its production and purity are critical for ensuring the efficacy and safety of the final anticancer drug.

Physical Properties

Melting Point: 117-119 °C(lit.)

Boiling Point: 437.216 °C at 760 mmHg

Flash Point: 210.499 °C

Density: 1.41 g/cm3

Analytical Data

Appearance: off-white solid