(2S,3R,5R)-5-Chloro-2-(((4-methylbenzoyl)oxy)-methyl)tetrahydrofuran-3-yl 4-methylbenzoate, CAS No. 141846-57-3

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141846-57-3

Catalog No. EBD2335421

CAS 141846-57-3

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

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Basic Information

Synonyms: (2S,3R,5R)-5-Chloro-2-(((4-methylbenzoyl)oxy)-methyl)tetrahydrofuran-3-yl4-methylbenzoate alpha-l-erythro-pentofuranosylchloride-2-deoxy-bis(4-methylbenzoate) 1-chloro-3,5-di-o-toluoyl-2-deoxy-l-ribofuranose 1-chloro-2-deoxy-3,5-di-o-toluoyl-l-ribose 2-deoxy-3,5-di-o-p-toluoyl-α-l-ribofuranosylchloride 2-deoxy-α-l-erythro-pentofuranosylchloride3,5-bis(4-methylbenzoate) chloro-3,5-di-o-toluoyl-2-deoxy-α-l-ribofuranose 2-deoxy-3,5-di-o-p-toluoyl-a-l-ribofuranosylchloride 2-deoxy-a-l-erythro-pentofuranosylchloride3,5-bis(4-methylbenzoate)

Molecular Formula: C21H21ClO5

Molecular Weight: 388.84

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates

Product Description:

1-Chloro-2-deoxy-3,5-di-O-p-toluoyl-L-ribofuranose is a key chiral synthetic intermediate, specifically a protected L-ribofuranose derivative. Its structure features a reactive chlorine atom at the anomeric carbon (C1) and p-toluoyl protecting groups on the 3- and 5-hydroxyl positions. This configuration makes it a crucial building block for the synthesis of L-nucleoside analogs. This compound is primarily employed in the pharmaceutical research and development of antiviral and anticancer nucleoside drugs. It serves as a fundamental precursor for constructing the sugar moiety of L-nucleosides, such as Lamivudine (3TC) and other related therapeutic agents. The chiral integrity of the L-ribose scaffold is essential for the biological activity and metabolic stability of the final drug molecules. As a specialized, application-driven intermediate, it is not a general-purpose synthetic reagent. Its synthesis and use are highly targeted within medicinal chemistry for the preparation of bioactive nucleoside derivatives, highlighting its role in the development of novel therapeutics.

Physical Properties

Melting Point: 117-119°C

Boiling Point: 518.414 °C at 760 mmHg

Flash Point: 185.58 °C

Density: 1.283 g/cm3

Analytical Data

Appearance: White Solid