(3'S,5'R)-N⁶-benzoyl-9-<2'-deoxy-5'-O-<(4,4'-dimethoxytriphenyl)methyl>-3',5'-ethano-α-D-ribofuranosyl>adenine

Base Information

• Chemical Name: (3'S,5'R)-N⁶-benzoyl-9-<2'-deoxy-5'-O-<(4,4'-dimethoxytriphenyl)methyl>-3',5'-ethano-α-D-ribofuranosyl>adenine
• CAS No.: 174692-10-5
• Molecular Formula: C₄₀H₃₇N₅O₆
• Molecular Weight: 683.764

Synonyms:(3'S,5'R)-N⁶-benzoyl-9-<2'-deoxy-5'-O-<(4,4'-dimethoxytriphenyl)methyl>-3',5'-ethano-α-D-ribofuranosyl>adenine

Chemical Property of (3'S,5'R)-N⁶-benzoyl-9-<2'-deoxy-5'-O-<(4,4'-dimethoxytriphenyl)methyl>-3',5'-ethano-α-D-ribofuranosyl>adenine

Chemical Property:

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Technology Process of (3'S,5'R)-N⁶-benzoyl-9-<2'-deoxy-5'-O-<(4,4'-dimethoxytriphenyl)methyl>-3',5'-ethano-α-D-ribofuranosyl>adenine

There total 1 articles about (3'S,5'R)-N⁶-benzoyl-9-<2'-deoxy-5'-O-<(4,4'-dimethoxytriphenyl)methyl>-3',5'-ethano-α-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: 79.0%

(3'S,5'R)-N6-benzoyl-9-(2'-deoxy-3',5'-ethano-α-D-ribofuranosyl)adenine (174692-09-2) + 4,4’-dimethoxytrityl trifluoromethanesulfonate (239808-67-4) → (3'S,5'R)-N6-benzoyl-9-<2'-deoxy-5'-O-<(4,4'-dimethoxytriphenyl)methyl>-3',5'-ethano-α-D-ribofuranosyl>adenine (174692-10-5)

Guidance literature:

With pyridine; for 2h; Ambient temperature;

DOI:10.1002/hlca.19950780816

Reference yield: 81.0%

(chloro)(diisopropylamino)[(prop-2-enyl)oxy]phosphine (174617-87-9) + (3'S,5'R)-N6-benzoyl-9-<2'-deoxy-5'-O-<(4,4'-dimethoxytriphenyl)methyl>-3',5'-ethano-α-D-ribofuranosyl>adenine (174692-10-5) → (3'S,5'R)-9-<3'-O-<(allyloxy)(diisopropylamino)phosphino>-2'-deoxy-5'-O-<(4,4'-dimethoxytriphenyl)methyl>-3',5'-ethano-α-D-ribofuranosyl>-N6-benzoyladenine

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 4.5h; Ambient temperature;

DOI:10.1002/hlca.19950780816

Reference yield:

(3'S,5'R)-N6-benzoyl-9-<2'-deoxy-5'-O-<(4,4'-dimethoxytriphenyl)methyl>-3',5'-ethano-α-D-ribofuranosyl>adenine (174692-10-5) → (3'S,5'R)-N6-benzoyl-9-<2'-deoxy-5'-O-<(4,4'-dimethoxytriphenyl)methyl>-3',5'-ethano-3'-O-<4-(4-nitrophenyloxy)succinyl>-α-D-ribofuranosyl>adenine

Guidance literature:

Multi-step reaction with 2 steps

1: 204 mg / 4-(dimethylamino)pyridine / pyridine / 70 h / Ambient temperature

2: dicyclohexylcarbodiimide / dioxane / 1.33 h / Ambient temperature

With dmap; dicyclohexyl-carbodiimide; In 1,4-dioxane; pyridine;

DOI:10.1002/hlca.19950780816

upstream raw materials:

(3'S,5'R)-N⁶-benzoyl-9-(2'-deoxy-3',5'-ethano-α-D-ribofuranosyl)adenine

4,4’-dimethoxytrityl trifluoromethanesulfonate

Downstream raw materials:

Succinic acid mono-{(2S,3aS,6R,6aR)-2-(6-benzoylamino-purin-9-yl)-6-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-hexahydro-cyclopenta[b]furan-3a-yl} ester

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