N6-Benzoyl-9-(2'-deoxy-5'-O-DMT-2'-fluoro-b-D-arabinofuranosyl)adenine 3'-CE-phosphoramidite - CAS 329187-86-2

Catalog number: BRA-036

N6-Benzoyl-9-(2'-deoxy-5'-O-DMT-2'-fluoro-b-D-arabinofuranosyl)adenine 3'-CE-phosphoramidite is an antiviral agent that inhibits the replication of DNA.

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Ordering Information

Catalog Number	Size	Price	Stock	Quantity
BRA-036	1 g	$1449	In stock

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Synonyms

N6-Bz-5'-O-DMTr-2'-fluoro-2'-deoxyarabinoadenosine-3'-CEN-phosphoramidite; 2'-Fluoro-2'-deoxy-ara-A-3'-phosphoramidite; N6-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-fluoro-2'-deoxyarabinoadenosine-3'-O-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite; 5'-O-DMT-N6-Benzoyl-2'-fluoro-2'-arabinofuranosyl-2'-deoxyadenosine 3'-CE phosphoramidite; 9-{5-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-3-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-2-deoxy-2-fluoro-β-D-arabinofuranosyl}-6-{[hydroxy(phenyl)methylene]amino}-9H-purine

CAS

329187-86-2

IUPAC Name

N-[9-[(2R,3S,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-fluorooxolan-2-yl]purin-6-yl]benzamide

Molecular Weight

875.92

Molecular Formula

C47H51FN7O7P

Canonical SMILES

CC(C)N(C(C)C)P(OCCC#N)OC1C(OC(C1F)N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)COC(C5=CC=CC=C5)(C6=CC=C(C=C6)OC)C7=CC=C(C=C7)OC

InChI

InChI=1S/C47H51FN7O7P/c1-31(2)55(32(3)4)63(60-27-13-26-49)62-42-39(61-46(40(42)48)54-30-52-41-43(50-29-51-44(41)54)53-45(56)33-14-9-7-10-15-33)28-59-47(34-16-11-8-12-17-34,35-18-22-37(57-5)23-19-35)36-20-24-38(58-6)25-21-36/h7-12,14-25,29-32,39-40,42,46H,13,27-28H2,1-6H3,(H,50,51,53,56)/t39-,40+,42-,46-,63?/m1/s1

InChIKey

VCCMVPDSLHFCBB-SAHKUVNLSA-N

Boiling Point

905.8±75.0°C at 760 mmHg

Purity

≥95%

Chemical Structure:

Reference Reading

1. Synthesis of some purine and pyrimidine nucleosides of 3-amino-2,3,6-trideoxy-L-lyxo-hexopyranose (daunosamine)

E Lazzari, A Vigevani, F Arcamone. Carbohydr Res. 1977 Jun;56(1):35-42. doi: 10.1016/s0008-6215(00)84234-2.

The daunosaminyl analogue of the antibiotic puromycin and the nucleoside derivatives of daunosamine with adenine, thymine, and cytosine have been synthesised. The nucleoside derivatives of 6-dimethylaminopurine, thymine, and cytosine were prepared by melting the protected daunosamine with the protected base in vacuo. Daunosaminyladenine was obtained by condensing N-trifluoroacetyl-O-trifluoroacetyl-alpha-daunosaminyl chloride either with N6-benzoyl-9-chloromercuryadenine in boiling xylene or with N6-benzoyladenine in dichloromethane at room temperature in the presence of a molecular sieve. In each reaction, the beta-anomeric nucleoside was obtained, as shown by p.m.r. data. The protecting groups were removed with barium hydroxide or methanolic ammonia to give the free aminonucleosides in good yield. 9-beta-Daunosaminyl-6-dimethylaminopurine was coupled to N-benzylocyxcarbonyl-O-methyltyrosine, giving, after hydrogenolysis, the daunosaminyl analogue of puromycin.

2. An approach to the total synthesis of sinefungin

G A Mock, J G Moffatt. Nucleic Acids Res. 1982 Oct 25;10(20):6223-34. doi: 10.1093/nar/10.20.6223.

Condensation of N6-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde with nitromethane followed by acid catalyzed acetylation and borohydride reduction leads to N6-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-6-nitro-beta-D-ribo-hexofuranosyl)adenine (4). A second nitroaldol condensation between 4 and N-benzyloxycarbonly-L-aspartic acid-beta-semialdehyde alpha-benzyl ester (5) followed by acetylation and borohydride reduction leads to a fully protected 6'-nitro modification of sinefungin and its C6'-epimer (7). Hydrolysis of the acetonide followed by sequential reduction of the benzyl derived protecting groups and the nitro group and debenzoylation leads to a modest yield of a 3: 1 mixture of sinefungin (1) and 6'-episinefungin which can only be separated by analytical ion exchange chromatography.