2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate, CAS No. 122111-11-9

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122111-11-9

Catalog No. EBD42576

CAS 122111-11-9

Name 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate

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Basic Information

Synonyms: D-erythro-pentofuranose,2-deoxy-2,2-difluoro-,3,5-dibenzoate1-methanesulfonate 2-dexy-2,2-difluoro-3,5-o-dibenzoylribosemesylate 2-deoxy-2,2-difluoro-d-erythro-ribofuranose-3,5-dibenzoate1-methanesulfonate 2-deoxy-2,2-difluoro-d-ribofuranose-3,5-dibenzoate-1-methanesulfonate 2-Deoxy-2,2-difluoro-3,5-dibenzoyl-D-ribofuranose-1-methanesulfonate 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate-1-methanesulfonate 4-amino-1-[(2S,4S,5S)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate(racemate) 2-Deoxy-2,2-Difluoro-D-Erythro-Pentofuranose-3,5-Dibenzoate-1-Methanesulfonate(T8) 2-Deoxy-2,2,-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate D-erythro-pentofuranose,

Molecular Formula: C20H18F2O8S

Molecular Weight: 456.41

MDL Number: MFCD08460089

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

Product Description:

2-Deoxy-2,2-difluoro-D-erythro-pentofuranosyl 3,5-dibenzoate 1-methanesulfonate is a key chiral synthetic intermediate. Its structure features a difluorinated ribose sugar core protected with benzoate groups and activated at the anomeric position with a mesylate leaving group. This compound is a crucial building block in the synthesis of nucleoside analogs, most notably for the production of the anticancer drug Gemcitabine. The mesylate group at the 1-position is highly reactive, facilitating the subsequent glycosylation step to attach the nucleobase, which is a critical transformation in the final stages of the API synthesis. The D-erythro configuration and the 2',2'-difluoro modification are essential for the biological activity of the final drug. As a high-value, purpose-designed intermediate, its primary and almost exclusive application is within the pharmaceutical manufacturing supply chain for specific active pharmaceutical ingredients (APIs). Its synthesis and handling require expertise in carbohydrate and fluorinated chemistry.

Physical Properties

Boiling Point: 588.439 °C at 760 mmHg

Flash Point: 309.677 °C

Density: 1.464 g/cm3

Analytical Data

Appearance: Brown liquid