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

Base Information

• Chemical Name: (3'S,5'R,6'S)-N⁶-benzoyl-9-(2'-deoxy-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl)adenine
• CAS No.: 200931-85-7
• Molecular Formula: C₂₀H₁₉N₅O₄
• Molecular Weight: 393.402

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

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

There total 8 articles about (3'S,5'R,6'S)-N⁶-benzoyl-9-(2'-deoxy-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: 81.0%

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'S)-N6-benzoyl-9-(2'-deoxy-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl)adenine (200931-85-7)

Guidance literature:

With pyridine hydrogenfluoride; at 20 ℃; for 4h;

DOI:10.1002/chem.200600597

Reference yield: 76.0%

N-{9-[(1aR,1bS,3S,4aS,5aS)-1a-(tert-Butyl-dimethyl-silanyloxy)-4a-trimethylsilanyloxy-octahydro-2-oxa-cyclopropa[a]pentalen-3-yl]-9H-purin-6-yl}-benzamide (200931-83-5) → (3'S,5'R,6'S)-N6-benzoyl-9-(2'-deoxy-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl)adenine (200931-85-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; 2.5 h, room t. and 1.5 h, 50 deg C;

DOI:10.1002/hlca.19970800812

Reference yield:

(1'R,5'R,6'S)-(6'-hydroxy-3',3'-dimethyl-2',4'-dioxabicyclo[3.3.0]oct-6'-yl)acetaldehyde → (3'S,5'R,6'S)-N6-benzoyl-9-(2'-deoxy-3',5'-ethano-5',6'-methano-α-D-ribofuranosyl)adenine (200931-85-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / Amberlyst 15 (H⁺ form) / 16 h, room t. and 2 h, reflux

2: 67 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3-(1H)-one / CH₂Cl₂ / 2 h / Ambient temperature

3: 1.) LDA / 1.) THF, -74 deg C, 45 min, 2.) THF, Et₃N, -74 deg C and room t., 2 h

4: 1.) Ag-Zn / 1.) Et₂O, 1 h, room t., 2.) Et₂O, 3 h, reflux

5: 42 percent / CF₃SO₃SiMe₃ / 1,2-dichloro-ethane / 7 h / 83 °C

6: 76 percent / Bu₄NF / tetrahydrofuran; hexane / 2.5 h, room t. and 1.5 h, 50 deg C

With zinc-silver couple; trimethylsilyl trifluoromethanesulfonate; Amberlyst 15 (H⁺ form); tetrabutyl ammonium fluoride; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/hlca.19970800812

upstream raw materials:

N-{9-[(1aR,1bS,3S,4aS,5aS)-1a-(tert-Butyl-dimethyl-silanyloxy)-4a-trimethylsilanyloxy-octahydro-2-oxa-cyclopropa[a]pentalen-3-yl]-9H-purin-6-yl}-benzamide

(1R,5R,6S)-6-(2'-hydroxyethyl)-3,3-dimethyl-2,4-dioxabicyclo[3.3.0]octan-6-ol

(1aR,1bS,4aS,5aR)-1a-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-hexahydro-2-oxa-cyclopropa[a]pentalen-4a-ol

Downstream raw materials:

(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

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