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161599-46-8 (2′,3′-Di-O-acetyl-5′-deoxy-5-fluoro-D-cytidine)

161599-46-8 (2′,3′-Di-O-acetyl-5′-deoxy-5-fluoro-D-cytidine) Manufacturers in Hyderabad, India

Overview & Chemical Identity

CAS Number: 161599-46-8

Chemical Name: 2′,3′-Di-O-acetyl-5′-deoxy-5-fluoro-D-cytidine

IUPAC Name:
(2R,3S,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-(acetyloxymethyl)oxolane-3,4-diyl diacetate

Synonyms:
2′,3′-Diacetyl-5′-deoxy-5-fluorocytidine;
Protected 5-fluoro-D-cytidine derivative;
Di-O-acetyl 5-fluoro cytidine intermediate

Molecular Formula: C₁₃H₁₆FN₃O₇

Molecular Weight: ~345.28 g/mol

Physical & Chemical Properties

Appearance: White to off-white crystalline powder

Physical State: Solid

Melting Point: Typically reported in the range of 150–170 °C (may vary depending on purity)

Boiling Point: Not applicable (decomposes upon strong heating)

Solubility:
Soluble in polar organic solvents such as methanol, ethanol, acetonitrile, and DMSO; limited solubility in water due to acetyl protection

Stability:
Stable under dry, controlled laboratory conditions; hydrolyzes under strongly acidic or basic conditions; sensitive to prolonged moisture exposure

Structural & Molecular Identifiers

Functional Groups:

  • Fluorinated pyrimidine base (5-fluorocytosine moiety)

  • Ribose sugar derivative

  • Two acetyl ester groups (–OCOCH₃)

  • Amide (cytosine carbonyl group)

  • Heterocyclic nitrogen atoms

Chemical Class:

Fluorinated nucleoside derivative / Protected pyrimidine nucleoside

SMILES (representative):
CC(=O)O[C@H]1C@HC@HO[C@H]1CO

InChI Key (representative):
(Varies by database; available from chemical registries)

Functionality & Applications

Protected Nucleoside Intermediate

161599-46-8 is a protected fluorinated nucleoside used primarily as an intermediate in pharmaceutical synthesis. The acetyl groups serve to:

  • Protect hydroxyl functionalities

  • Improve lipophilicity

  • Enhance reaction selectivity

  • Enable controlled deprotection in multi-step synthesis

The 5-fluoro substitution significantly modifies biological activity and metabolic stability.

Pharmaceutical Applications

This compound is widely used in:

  • Anticancer drug development

  • Antiviral research

  • Synthesis of fluoropyrimidine-based APIs

  • Preparation of nucleoside analog therapeutics

Fluorinated cytidine derivatives are structurally related to well-known chemotherapeutic agents used in oncology.

Nucleoside & Prodrug Chemistry

Commonly employed in:

  • Synthesis of modified RNA/DNA building blocks

  • Development of prodrug strategies

  • Glycosylation and phosphorylation reactions

  • Structure–activity relationship (SAR) studies

Acetyl protection enhances membrane permeability and improves handling during synthetic processes.

Research & Development

Used in:

  • Medicinal chemistry laboratories

  • Oncology drug research

  • Antimetabolite development programs

  • Enzyme inhibition studies

  • Advanced carbohydrate chemistry research

Its dual nature as both a nucleobase and sugar-modified compound makes it highly valuable in nucleoside chemistry.

Safety & Handling

GHS Classification (typical for similar fluorinated nucleoside intermediates):

  • Harmful if swallowed

  • May cause skin and eye irritation

  • May cause respiratory irritation

Common Hazard Statements:

  • H302: Harmful if swallowed

  • H315: Causes skin irritation

  • H319: Causes serious eye irritation

  • H335: May cause respiratory irritation

Precautionary Statements:

  • P261: Avoid breathing dust

  • P280: Wear protective gloves and eye protection

  • P305 + P351 + P338: IF IN EYES, rinse cautiously with water

  • P301 + P312: IF SWALLOWED, call a doctor if you feel unwell

Handle in a well-ventilated laboratory using appropriate personal protective equipment (PPE).

Practical Details & Supplier Information

Typical Purity: 98–99% (Research and Pharmaceutical Intermediate Grade)

Storage Conditions:

  • Store in a tightly sealed container

  • Keep in a cool, dry environment

  • Protect from moisture and direct sunlight

  • Avoid strong acids and bases

Commercial Use:
Available from specialty chemical manufacturers for pharmaceutical intermediate production, nucleoside synthesis, and advanced research applications.
Not intended for direct pharmaceutical, food, or diagnostic use without proper regulatory compliance.

Summary Statement

161599-46-8 (2′,3′-DI-O-ACETYL-5′-DEOXY-5-FLUORO-D-CYTIDINE) is an important fluorinated nucleoside intermediate widely utilized in pharmaceutical and medicinal chemistry applications. Its acetyl-protected sugar moiety and 5-fluoro-substituted cytosine base make it a valuable building block in anticancer, antiviral, and nucleoside analog research, supporting advanced synthetic and therapeutic development programs.

As a trusted manufacturer and supplier in Hyderabad, SriniChem provides high-quality 161599-46-8 (2′,3′-DI-O-ACETYL-5′-DEOXY-5-FLUORO-D-CYTIDINE) produced under strict quality control standards. Our product, with CAS No: 161599-46-8, is suitable for both research and industrial use. Choose SriniChem for reliable supply, technical expertise, and customer-focused service. Contact SriniChem today for 2′,3′-DI-O-ACETYL-5′-DEOXY-5-FLUORO-D-CYTIDINE.

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