N⁶-benzoyl-9-(3-O-tert-butyldimethylsily-2-O-methyl-β-D-xylofuranos-5-urosyl)adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-(3-O-tert-butyldimethylsily-2-O-methyl-β-D-xylofuranos-5-urosyl)adenine
• CAS No.: 252000-89-8
• Molecular Formula: C₂₄H₃₁N₅O₅Si
• Molecular Weight: 497.626

Synonyms:N⁶-benzoyl-9-(3-O-tert-butyldimethylsily-2-O-methyl-β-D-xylofuranos-5-urosyl)adenine

Chemical Property of N⁶-benzoyl-9-(3-O-tert-butyldimethylsily-2-O-methyl-β-D-xylofuranos-5-urosyl)adenine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-benzoyl-9-(3-O-tert-butyldimethylsily-2-O-methyl-β-D-xylofuranos-5-urosyl)adenine

There total 6 articles about N⁶-benzoyl-9-(3-O-tert-butyldimethylsily-2-O-methyl-β-D-xylofuranos-5-urosyl)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:

N6-benzoyl-9-(3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-xylofuranosyl)adenine (252000-88-7) → N6-benzoyl-9-(3-O-tert-butyldimethylsily-2-O-methyl-β-D-xylofuranos-5-urosyl)adenine (252000-89-8)

Guidance literature:

With dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In pyridine; at 20 ℃; for 2h;

DOI:10.1021/ja992608h

Reference yield:

2'-O-methyl adenosine (2140-79-6) → N6-benzoyl-9-(3-O-tert-butyldimethylsily-2-O-methyl-β-D-xylofuranos-5-urosyl)adenine (252000-89-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / pyridine / 12 h / 60 °C

2: CrO₃; Ac₂O; pyridine / CH₂Cl₂ / 0 °C

3: NaBH₄; AcOH / 12 h / 4 °C

4: imidazole / dimethylformamide / 15 h / 20 °C

5: pyridine / 3 h / 20 °C

6: 81 percent / 80 percent aq. TFA / CH₂Cl₂ / 1 h / 20 °C

7: DCC; DMSO; CF₃COOH / pyridine / 2 h / 20 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; sodium tetrahydroborate; acetic anhydride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Oxidation / 3: Reduction / 4: silylation / 5: Acylation / 6: trityl deprotection / 7: Oxidation;

DOI:10.1021/ja992608h

Reference yield:

(2R,4S,5R)-5-(6-Amino-purin-9-yl)-4-methoxy-2-trityloxymethyl-dihydro-furan-3-one → N6-benzoyl-9-(3-O-tert-butyldimethylsily-2-O-methyl-β-D-xylofuranos-5-urosyl)adenine (252000-89-8)

Guidance literature:

Multi-step reaction with 5 steps

1: NaBH₄; AcOH / 12 h / 4 °C

2: imidazole / dimethylformamide / 15 h / 20 °C

3: pyridine / 3 h / 20 °C

4: 81 percent / 80 percent aq. TFA / CH₂Cl₂ / 1 h / 20 °C

5: DCC; DMSO; CF₃COOH / pyridine / 2 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: silylation / 3: Acylation / 4: trityl deprotection / 5: Oxidation;

DOI:10.1021/ja992608h

upstream raw materials:

N⁶-benzoyl-9-(3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-xylofuranosyl)adenine

2'-O-methyl adenosine

9-(2-O-methyl-5-O-trityl-β-D-xylofuranosyl)adenine

N⁶-benzoyl-9-(3-O-tert-butyldimethylsilyl-2-O-methyl-5-O-trityl-β-D-xylofuranosyl)adenine

Downstream raw materials:

3-[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-ylmethyl]-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester

3-{[5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester

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