2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine

Base Information

• Chemical Name: 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine
• CAS No.: 161599-46-8
• Molecular Formula: C13H16FN3O6
• Molecular Weight: 329.285
• Hs Code.: 29389090
• European Community (EC) Number: 605-260-4
• Mol file: 161599-46-8.mol

Synonyms:5'-Deoxy-2',3'-di-O-acetyl-5-fluorocytidine;

Chemical Property of 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine

Chemical Property:

• Appearance/Colour: WHITE
• Melting Point: 196-198?C
• Boiling Point: 427.4 °C at 760 mmHg
• PKA: 2.49±0.10(Predicted)
• Flash Point: 212.3 °C
• PSA: 122.74000
• Density: 1.57 g/cm³
• LogP: 0.32650
• Storage Temp.: -20°C Freezer
• Solubility.: soluble in Methanol
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 329.10231340
• Heavy Atom Count: 23
• Complexity: 605

Purity/Quality:

99% ^*data from raw suppliers

2’,3’-Di-O-acetyl-5’-deoxy-5-fluorocytidine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(O1)N2C=C(C(=NC2=O)N)F)OC(=O)C)OC(=O)C
• Uses: Capecitabine intermediate A metabolite of Capecitabine. A metabolite of Capecitabine. Capecitabine Diacetyl Amino Impurity (USP).

Technology Process of 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine

There total 30 articles about 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.1%

2',3'-di-O-ethanoyl-5-fluorocytidine (1054449-33-0) → (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate (161599-46-8,2230479-30-6)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In chloroform; at -10 - -5 ℃; for 3h; Solvent; Temperature; Inert atmosphere;

Reference yield: 88.6%

Flucytosine (2022-85-7) + 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose (27821-07-4,27930-18-3,37076-71-4,62211-93-2,63903-44-6,76497-54-6) → (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate (161599-46-8,2230479-30-6)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 10 - 20 ℃; for 4h; Solvent;

Reference yield: 86.0%

di-O-acetyl-5-deoxy-ξ-D-ribofuranosyl chloride (110022-91-8) + 2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine (111878-21-8) → (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate (161599-46-8,2230479-30-6)

Guidance literature:

di-O-acetyl-5-deoxy-ξ-D-ribofuranosyl chloride; 2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine; In 1,2-dichloro-ethane; for 4h; Inert atmosphere; Schlenk technique; Reflux;

With water; Inert atmosphere; Schlenk technique;

DOI:10.3390/molecules22010084

upstream raw materials:

Flucytosine

1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose

5'-deoxy-5-fluorocytidine

5'-deoxy-2',3'-di-O-acetyl-5-fluoro-N₄-((5-nitrothien-2-yl)methoxycarbonyl)cytidine

Downstream raw materials:

N¹-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N⁴-(pentyloxycarbonyl)cytosine

Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[5-fluoro-2-oxo-4-(3,4,5-trimethoxy-benzoylamino)-2H-pyrimidin-1-yl]-5-methyl-tetrahydro-furan-3-yl ester

Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-butoxycarbonylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester

5'-deoxy-5-fluoro-N⁴-(3,4,5-trimethoxybenzoyl)cytidine