Welcome to chemicalbook!
Chinese English Japanese Germany Korea
010-86108875
logo
Inquriy
Try our best to find the right business for you.
Messages
Do not miss inquiry messages Please log in to view all inquiry messages.
My chemicalbook

Welcome back!

Structured search
18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
ChemicalBook CAS DataBase List 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine
1011529-10-4

4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine synthesis

3synthesis methods
The synthesis is carried out starting from benzoyl protected fluorofuranose 1.1. Bromination with HBr in acetic acid followed by displacement of bromide 1.2 with protected cytosine 1.3 gives intermediate 1.4. Deprotection of the benzoyl group with ammonia in methanol gives diol 1.5, which is then converted to the alkyl iodide 1.6 via a Mitsunobu reaction. Elimination of iodine with sodium methoxide followed by addition of sodium azide and iodine chloride to the resulting olefin gives azide 1.7. Both the alcohol and amine are reprotected with benzoyl chloride, and the iodine is displaced by m-chlorobenzoic acid in an oxidative nucleophilic substitution reaction to give the penultimate intermediate 1.9. All protecting groups are then removed in methanol-ammonia to give azithromycin (1).
4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine
2(1H)-Pyrimidinone, 1-(5-O-acetyl-4-C-azido-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-4-amino-

1030595-44-8
2 suppliers
inquiry

4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine

1011529-10-4
61 suppliers
inquiry

-

Yield:1011529-10-4 89%

Reaction Conditions:

with methanol;triethylamine at 20; for 12 h;

Steps:

1

The synthesis of compound xv: The compound xiv (5mmol) was dissolved in 5% methanol-triethylamine (100ml), and the solution was stirred at a room temperature for 12 hours. After completion of the reaction, the solvent was removed through evaporation and the residue was purified by column chromatography to obtain the compound xv (89.0%).ESI-MS: 287[M+H]. 1H NMR(DMSO-d6, 300 MHz)δ: 8.14 (d, 1H), 7.32 (d, 1H), 7.21 (br, 2H), 6.08 (dd, 1H), 5.82 (d, 1H), 5.11 (t, 1H), 4.92 (dt, 1H), 4.16 (dt, 1H), 3.62-3.69 (m, 2H).

References:

EP2177527,2010,A1 Location in patent:Page/Page column 12

4'-Azido-3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-beta-D-arabinouridine

1145869-37-9
6 suppliers
inquiry

4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine

1011529-10-4
61 suppliers
inquiry

References
1333126-30-9 Synthesis
4’-Azido-3’-O-benzoyl-5’-O-(m-chlorobenzoyl)-2’-deoxy-2’-fluoro-beta-D-arabinouridine

1333126-30-9
22 suppliers
inquiry

4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine

1011529-10-4
61 suppliers
inquiry

References