9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-5-phenyl-β-D-ribofuranosyl]adenine

Base Information

Chemical Name:9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-5-phenyl-β-D-ribofuranosyl]adenine
CAS No.:885671-72-7
Molecular Formula:C₃₆H₃₉N₅O₈
Molecular Weight:669.734
Hs Code.:

Synonyms:9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-5-phenyl-β-D-ribofuranosyl]adenine

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Chemical Property of 9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-5-phenyl-β-D-ribofuranosyl]adenine

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Technology Process of 9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-5-phenyl-β-D-ribofuranosyl]adenine

There total 17 articles about 9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-5-phenyl-β-D-ribofuranosyl]adenine 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: 100.0%

: 518332-50-8
Isobutyric acid (2R,3R,4R,5R)-2-(6-benzoylamino-purin-9-yl)-5-benzyl-4-((2R,3R,4S,5R,6R)-3-benzyloxy-6-benzyloxymethyl-4,5-bis-isobutyryloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester

: 885671-72-7
9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-5-phenyl-β-D-ribofuranosyl]adenine

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 24h;
DOI:10.1021/ol0602710

Reference yield:

: 518332-41-7
2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-phenylsulfinyl-β-D-glucopyranoside

: 885671-72-7
9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-5-phenyl-β-D-ribofuranosyl]adenine

Guidance literature:: Multi-step reaction with 9 steps

1.1: 78 percent / 2,6-di-tert-butyl-4-methylpyridine / diethyl ether / 8 h / -78 °C

2.1: 82 percent / TBAF / tetrahydrofuran / 20 °C

3.1: tetrahydrofuran / 20 °C

4.1: PhOCSCl; DMAP / acetonitrile / 20 °C

4.2: 93 percent / Bu₃SnH; AIBN / toluene / Heating

5.1: aq. TFA / 20 °C

6.1: Et₃N; DMAP / acetonitrile / 20 °C

7.1: hexamethyldisilazane; pyridine

7.2: 60 percent / SnCl₄ / acetonitrile / 20 °C

8.1: 100 percent / NaOMe / methanol / 20 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; sodium methylate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; phenylcarbonochloridothioate; In tetrahydrofuran; methanol; diethyl ether; acetonitrile; 3.1: Moffatt oxidation / 5.2: Barton deoxygenation / 8.2: Vorbrueggen glycosylation;
DOI:10.1021/jm060310d

Reference yield:

: 518332-60-0
3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-phenyl-α-D-ribofuranose

: 885671-72-7
9-[5-deoxy-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-5-phenyl-β-D-ribofuranosyl]adenine

Guidance literature:: Multi-step reaction with 5 steps

1.1: PhOCSCl; DMAP / acetonitrile / 20 °C

1.2: 93 percent / Bu₃SnH; AIBN / toluene / Heating

2.1: aq. TFA / 20 °C

3.1: Et₃N; DMAP / acetonitrile / 20 °C

4.1: hexamethyldisilazane; pyridine

4.2: 60 percent / SnCl₄ / acetonitrile / 20 °C

5.1: 100 percent / NaOMe / methanol / 20 °C

With pyridine; dmap; sodium methylate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; phenylcarbonochloridothioate; In methanol; acetonitrile; 1.2: Barton deoxygenation / 4.2: Vorbrueggen glycosylation;
DOI:10.1021/jm060310d