Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester
• CAS No.: 200404-37-1
• Molecular Formula: C₂₅H₃₄F₃N₅O₁₀S
• Molecular Weight: 653.634

Synonyms:Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester

Chemical Property of Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester

Chemical Property:

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Technology Process of Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester

There total 1 articles about Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester 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:

9-β-D-arabinofuranosylguanine (38819-10-2) → Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester (200404-37-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) TMSCl, pyridine, 3.) NH₄OH

2: TsOH / dioxane

3: DMAP / CH₂Cl₂

With pyridine; dmap; ammonium hydroxide; chloro-trimethyl-silane; toluene-4-sulfonic acid; In 1,4-dioxane; dichloromethane;

DOI:10.1080/07328319708006246

Reference yield:

Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester (200404-37-1) → 2'-deoxy-2'-fluoroguanosine (78842-13-4)

Guidance literature:

Multi-step reaction with 3 steps

1: TBAF / tetrahydrofuran

2: Dowex-50 / methanol

3: NH₄OH / 24 h / 55 °C

With ammonium hydroxide; Dowex-50; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol;

DOI:10.1080/07328319708006246

Reference yield:

Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester (200404-37-1) → N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide (144089-96-3)

Guidance literature:

Multi-step reaction with 3 steps

1: tertbutylammonium fluoride / tetrahydrofuran / 5 h / 5 °C

2: 41 percent / Dowex 50W x 2-100 / methanol / 1 h / 23 °C

3: 87 percent / pyridine, Et₃N / 4 h / 23 °C

With pyridine; tert-butyl-ammonium fluoride; Dowex 50W x 2-100; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1021/jm00059a007

upstream raw materials:

9-β-D-arabinofuranosylguanine

Downstream raw materials:

2’-fluoro-N2-isobutyryl-2’-deoxyguanosine

2'-deoxy-2'-fluoroguanosine

N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide

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