5`-deoxy-5-fluore-N-[(pentoyloxy)carbonyl]cytidine 2`,3`-diacetate

Base Information

• Chemical Name: 5`-deoxy-5-fluore-N-[(pentoyloxy)carbonyl]cytidine 2`,3`-diacetate
• CAS No.: 162204-20-8
• Molecular Formula: C19H26FN3O8
• Molecular Weight: 443.429
• Hs Code.: 29349990
• Mol file: 162204-20-8.mol

Synonyms:Carbamicacid, [1-(2,3-di-O-acetyl-5-deoxy-b-D-ribofuranosyl)-5-fluoro-1,2-dihydro-2-oxo-4-pyrimidinyl]-, pentylester;2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl)cytidine;

Chemical Property of 5`-deoxy-5-fluore-N-[(pentoyloxy)carbonyl]cytidine 2`,3`-diacetate

Chemical Property:

• Appearance/Colour: Powder
• Melting Point: 100-102?C
• PKA: 5.36±0.40(Predicted)
• PSA: 135.05000
• Density: 1.4 g/cm³
• LogP: 1.97480
• Storage Temp.: Refrigerator
• Solubility.: soluble in Methanol

Purity/Quality:

99% ^*data from raw suppliers

2’,3’-Di-O-acetyl-5’-deoxy-5-fluoro-N4-(pentoxycarbonxyl)cytidine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2’,3’-Di-O-acetyl-5’-deoxy-5-fluoro-N4-(pentoxycarbonxyl)cytidine (cas# 162204-20-8) is a compound useful in organic synthesis.

Technology Process of 5`-deoxy-5-fluore-N-[(pentoyloxy)carbonyl]cytidine 2`,3`-diacetate

There total 27 articles about 5`-deoxy-5-fluore-N-[(pentoyloxy)carbonyl]cytidine 2`,3`-diacetate 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: 94.2%

pentyl chloroformate (638-41-5) + (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) → N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine (162204-20-8)

Guidance literature:

With potassium phosphate; In dichloromethane; isopropyl alcohol; at 0 - 25 ℃; for 4h; Reagent/catalyst; Inert atmosphere;

Reference yield: 93.0%

(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamic acid amyl ester (862508-03-0) + C24H24O7 → N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine (162204-20-8)

Guidance literature:

(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamic acid amyl ester; With N,O-Bis(trimethylsilyl)trifluoroacetamide; In acetonitrile; at 50 ℃; for 0.5h; Inert atmosphere;

C₂₄H₂₄O₇; In acetonitrile; at 20 ℃; for 0.75h; Inert atmosphere; Molecular sieve;

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 20 ℃; for 2h;

Reference yield: 91.6%

pentan-1-ol (71-41-0) + 1,1'-carbonyldiimidazole (530-62-1) + (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) → N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine (162204-20-8)

Guidance literature:

In dichloromethane; at 20 ℃; for 4h;

upstream raw materials:

pentyl chloroformate

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

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

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

Downstream raw materials:

capecitabine

Refernces

• 1、 -. "Preparation of capecitabine intermediate". Paragraph 0021-0024. . Retrieved 2021/09/01.
• 2、 -. "A capecitabine synthetic method". Paragraph 0018; 0019; 0020; 0022; 0025; 0028. . Retrieved 2018/06/21.