N⁶-benzoyl-9-[5-O-benzyl-3-deoxy-3-(3-O-benzyl-7-O-trityl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-β-D-ribo-pentofuranosyl]adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-[5-O-benzyl-3-deoxy-3-(3-O-benzyl-7-O-trityl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-β-D-ribo-pentofuranosyl]adenine
• CAS No.: 280574-44-9
• Molecular Formula: C₅₇H₅₅N₅O₉
• Molecular Weight: 954.092

Synonyms:N⁶-benzoyl-9-[5-O-benzyl-3-deoxy-3-(3-O-benzyl-7-O-trityl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-β-D-ribo-pentofuranosyl]adenine

Chemical Property of N⁶-benzoyl-9-[5-O-benzyl-3-deoxy-3-(3-O-benzyl-7-O-trityl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-β-D-ribo-pentofuranosyl]adenine

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Technology Process of N⁶-benzoyl-9-[5-O-benzyl-3-deoxy-3-(3-O-benzyl-7-O-trityl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-β-D-ribo-pentofuranosyl]adenine

There total 5 articles about N⁶-benzoyl-9-[5-O-benzyl-3-deoxy-3-(3-O-benzyl-7-O-trityl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-β-D-ribo-pentofuranosyl]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: 95.0%

trityl chloride (76-83-5) + N-{9-[(2R,3R,4S,5S)-4-((2R,3R,4S,5S,6R)-3-Benzyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylmethyl)-5-benzyloxymethyl-3-hydroxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide → N6-benzoyl-9-[5-O-benzyl-3-deoxy-3-(3-O-benzyl-7-O-trityl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-β-D-ribo-pentofuranosyl]adenine (280574-44-9)

Guidance literature:

With pyridine; at 0 - 50 ℃;

DOI:10.1016/S0040-4039(00)00171-4

Reference yield:

5-O-benzyl-1,2-di-O-acetyl-3-deoxy-3-(3-O-benzyl-4,5,7-tri-O-acetyl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-α,β-D-ribo-pentofuranose (280574-41-6) → N6-benzoyl-9-[5-O-benzyl-3-deoxy-3-(3-O-benzyl-7-O-trityl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-β-D-ribo-pentofuranosyl]adenine (280574-44-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HMDS; pyridine / 1 h / Heating

1.2: 265 mg / SnCl₄ / acetonitrile / 12 h / 0 - 20 °C

2.1: sodium methoxide / methanol / 0.83 h / 0 °C

3.1: 235 mg / pyridine / 1 h / 50 °C

With pyridine; sodium methylate; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; 1.1: silylation / 1.2: Vorbrueggen glycosylation / 2.1: Deacetylation / 3.1: Esterification;

DOI:10.1021/jo0001333

Reference yield:

N6-benzoyl-9-[5-O-benzyl-3-deoxy-3-(3-O-benzyl-4,5,7-tri-O-acetyl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-β-D-ribo-pentofuranosyl]adenine (280574-43-8) → N6-benzoyl-9-[5-O-benzyl-3-deoxy-3-(3-O-benzyl-7-O-trityl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-β-D-ribo-pentofuranosyl]adenine (280574-44-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methoxide / methanol / 0.83 h / 0 °C

2: 235 mg / pyridine / 1 h / 50 °C

With pyridine; sodium methylate; In methanol; 1: Deacetylation / 2: Esterification;

DOI:10.1021/jo0001333

upstream raw materials:

trityl chloride

N₆-benzoyladenine

5-O-benzyl-1,2-di-O-acetyl-3-deoxy-3-(3-O-benzyl-4,5,7-tri-O-acetyl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-α,β-D-ribo-pentofuranose

N⁶-benzoyl-9-[5-O-benzyl-3-deoxy-3-(3-O-benzyl-4,5,7-tri-O-acetyl-2,6-anhydro-1-deoxy-D-glycero-D-ido-heptitol-1-yl)-β-D-ribo-pentofuranosyl]adenine

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