(3'S,5'R,6'R)-N⁶-benzoyl-9-{2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl}adenine

Base Information

• Chemical Name: (3'S,5'R,6'R)-N⁶-benzoyl-9-{2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl}adenine
• CAS No.: 918886-47-2
• Molecular Formula: C₄₁H₃₇N₅O₆
• Molecular Weight: 695.775

Synonyms:(3'S,5'R,6'R)-N⁶-benzoyl-9-{2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl}adenine

Chemical Property of (3'S,5'R,6'R)-N⁶-benzoyl-9-{2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl}adenine

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of (3'S,5'R,6'R)-N⁶-benzoyl-9-{2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl}adenine

There total 2 articles about (3'S,5'R,6'R)-N⁶-benzoyl-9-{2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3',5'-ethano-5',6'-methano-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: 92.0%

4,4’-dimethoxytrityl trifluoromethanesulfonate (239808-67-4) + (3'S,5'R,6'S)-N6-benzoyl-9-(2'-deoxy-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl)adenine (200931-85-7) → (3'S,5'R,6'R)-N6-benzoyl-9-{2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl}adenine (918886-47-2)

Guidance literature:

In pyridine; at 20 ℃; for 3h;

DOI:10.1002/chem.200600597

Reference yield:

N-{9-[1a-(tert-butyl-dimethyl-silanyloxy)-4a-hydroxy-octahydro-2-oxa-cyclopropa[a]pentalen-3-yl]-9H-purin-6-yl}-benzamide → (3'S,5'R,6'R)-N6-benzoyl-9-{2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl}adenine (918886-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / HF*pyridine / 4 h / 20 °C

2: 92 percent / pyridine / 3 h / 20 °C

With pyridine hydrogenfluoride; In pyridine;

DOI:10.1002/chem.200600597

Reference yield: 83.0%

(3'S,5'R,6'R)-N6-benzoyl-9-{2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl}adenine (918886-47-2) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → (3'S,5'R,6'S)-N6-benzoyl-9-{3'-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl}adenine

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 2h;

DOI:10.1002/chem.200600597

upstream raw materials:

4,4’-dimethoxytrityl trifluoromethanesulfonate

(3'S,5'R,6'S)-N⁶-benzoyl-9-(2'-deoxy-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl)adenine

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