Description

1-Chloro-3,5-Di-O-P-Chlorobenzoyl-2-Deoxy-D-Ribose (CAS No. 3601-90-9) is a high-purity chlorinated ribose derivative widely used in pharmaceutical research and organic synthesis. With the molecular formula C₁₉H₁₅Cl₃O₅, this compound features a 2-deoxy-D-ribose backbone functionalized with p-chlorobenzoyl groups at the 3- and 5-positions and a chloro substituent at the 1-position. Its stereospecific structure ((2R,3S)-5-chloro-2-(((4-chlorobenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-chlorobenzoate) makes it a valuable intermediate for nucleoside analog synthesis, antiviral drug development, and carbohydrate chemistry applications. Offered as a white to off-white crystalline powder, it is characterized by high stability under inert conditions and compatibility with anhydrous reaction environments. Store in a tightly sealed container at 2-8°C to maintain optimal purity (>95% by HPLC).

Properties

• CAS Number: 3601-90-9
• Complexity: 515
• IUPAC Name: [(2R,3S)-5-chloro-3-(4-chlorobenzoyl)oxy-tetrahydrofuran-2-yl]methyl 4-chlorobenzoate
• InChI: InChI=1S/C19H15Cl3O5/c20-13-5-1-11(2-6-13)18(23)25-10-16-15(9-17(22)26-16)27-19(24)12-3-7-14(21)8-4-12/h1-8,15-17H,9-10H2/t15-,16+,17?/m0/s1
• InChI Key: QEHCZULNFYDPPL-RTKIROINSA-N
• Exact Mass: 427.998507
• Molecular Formula: C19H15Cl3O5
• Molecular Weight: 429.7
• SMILES: C1[C@@H]([C@H](OC1Cl)COC(=O)C2=CC=C(C=C2)Cl)OC(=O)C3=CC=C(C=C3)Cl
• Topological: 61.8
• Monoisotopic Mass: 427.998507
• Synonyms: 3601-90-9, 1-Chloro-3,5-Di-O-P-Chlorobenzoyl-2-Deoxy-D-Ribose, 695-046-7, (2R,3S)-5-Chloro-2-(((4-chlorobenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-chlorobenzoate, 1-Chloro-3,5-di-(p-chlorobenzoyl)-2-deoxy-D-ribose, 21740-23-8, 1-Chloro-3,5-di(4-chlorbenzoyl)-2-deoxy-D-ribose, (2R,3S)-5-Chloro-2-(((4-chlorobenzoyl)oxy)methyl)-tetrahydrofuran-3-yl 4-chlorobenzoate, 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose, MFCD00672145, 1-Chloro-3,5-di-(p-chlorobenzoyl)-2-deoxy-D-ribofuranose, SCHEMBL2182170, 3,5-O-Bis(4-chlorobenzoyl)-2-deoxy-D-ribofuranosyl chloride, [(2R,3S)-5-chloro-3-(4-chlorobenzoyl)oxyoxolan-2-yl]methyl 4-chlorobenzoate, AKOS015999555, MC03466, [(2R,3S)-5-CHLORO-3-(4-CHLOROBENZOYLOXY)OXOLAN-2-YL]METHYL 4-CHLOROBENZOATE, AS-74143, MC145897, CS-0017828, F10764, 1-Chloro-3 pound not5-di(4-chlorbenzoyl)-2-deoxy-D-ribose, 2-deoxy-3,5-di-O-(p-chlorobenzoyl)-ribofuranosyl chloride, 1-Chloro-3,5-di-(p-chlorobenzoyl)-2-deoxy-D-ribose, techn., 1-Chloro-3,5-di-O-(4-chlorobenzoyl)-2-deoxy-a-D-ribofuranose, 1-Chloro-3,5-di-O-(4-chlorobenzoyl)-2-deoxy-D-ribofuranose, 2-deoxy-3,5-bis-O-(p-chlorobenzoyl)-D-ribofuranosyl chloride, 3,5-Di-O-(p-chlorobenzoyl)-2-deoxy-a-D-ribofuranosyl Chloride, 1-A-CHLORO-3,5-DI-O-(4-CHLOROBENZOYL)-2-DEOXY-D-RIBOFURANOSE, D-erythro-Pentofuranosylchloride, 2-deoxy-, 3,5-bis(4-chlorobenzoate), 3,5-Di-O-(4-chlorobenzoyl)-2-deoxy-D-erythro-pentofuranosyl chloride;1-Chloro-3,5-di-O-(4-chlorobenzoyl)-2-deoxy-D-ribose;(2R,3S,4R, 5R)-5-Chloro-2-((4-chlorobenzoyloxy)methyl)-4-hydroxytetrahydrofuran-3-yl 4-chlorobenzoate;3,5-O-Bis(4-chlorobenzoyl)-

This compound is primarily employed as a key intermediate in the synthesis of modified nucleosides and nucleotide analogs, particularly for antiviral and anticancer research. Its chlorobenzoyl-protected groups enhance solubility in organic solvents, facilitating glycosylation reactions in oligonucleotide chemistry. Researchers also utilize it in the development of prodrugs targeting RNA viruses due to its ribose-like scaffold. Strict handling under inert atmospheres (e.g., argon) is recommended to prevent hydrolysis of the labile chloro substituent.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

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