N⁶-benzoyl-2',3',5'-trideoxy-3'-(hydroxymethyl)-5'-<(tritylthio)methyl>-1'a-carbaadenosine

Base Information

• Chemical Name: N⁶-benzoyl-2',3',5'-trideoxy-3'-(hydroxymethyl)-5'-<(tritylthio)methyl>-1'a-carbaadenosine
• CAS No.: 149551-11-1
• Molecular Formula: C₃₉H₃₇N₅O₂S
• Molecular Weight: 639.821

Synonyms:N⁶-benzoyl-2',3',5'-trideoxy-3'-(hydroxymethyl)-5'-<(tritylthio)methyl>-1'a-carbaadenosine

Chemical Property of N⁶-benzoyl-2',3',5'-trideoxy-3'-(hydroxymethyl)-5'-<(tritylthio)methyl>-1'a-carbaadenosine

Chemical Property:

Purity/Quality:

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Technology Process of N⁶-benzoyl-2',3',5'-trideoxy-3'-(hydroxymethyl)-5'-<(tritylthio)methyl>-1'a-carbaadenosine

There total 13 articles about N⁶-benzoyl-2',3',5'-trideoxy-3'-(hydroxymethyl)-5'-<(tritylthio)methyl>-1'a-carbaadenosine 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: 91.0%

N6-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-5'-<(tritylthio)methyl>-1'a-carbaadenosine (149551-10-0) → N6-benzoyl-2',3',5'-trideoxy-3'-(hydroxymethyl)-5'-<(tritylthio)methyl>-1'a-carbaadenosine (149551-11-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1002/hlca.19930760207

Reference yield:

5-norbornene-2-methanol (13360-81-1,15507-06-9,42070-72-4,42070-82-6,67505-46-8,67671-05-0,67671-06-1,69831-10-3,95-12-5) → N6-benzoyl-2',3',5'-trideoxy-3'-(hydroxymethyl)-5'-<(tritylthio)methyl>-1'a-carbaadenosine (149551-11-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 89 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

2: 1) (+)-(1R)-α-pinene, BH3-THF, 2) 30percent aq. H2O2, 3N aq. NaOH

3: pyridinium chlorochromate, Celite / CH₂Cl₂ / 4 h / Ambient temperature

4: 3-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 18 h / 4 °C

5: methanol / Heating

6: PPh₃, diethyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C

7: NH₃ / methanol / 2.5 h / 0 °C

9: 69 percent / NH₃ / methanol / 0.5 h / 0 °C

10: 80 percent / pyridine / CH₂Cl₂ / Ambient temperature

11: 91 percent / Bu₄NF * 3 H₂O / tetrahydrofuran / Ambient temperature

With pyridine; 1H-imidazole; sodium hydroxide; borane-THF; Celite; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; sodium hydrogencarbonate; 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/hlca.19930760207

Reference yield:

methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate (149654-56-8) → N6-benzoyl-2',3',5'-trideoxy-3'-(hydroxymethyl)-5'-<(tritylthio)methyl>-1'a-carbaadenosine (149551-11-1)

Guidance literature:

Multi-step reaction with 4 steps

2: 69 percent / NH₃ / methanol / 0.5 h / 0 °C

3: 80 percent / pyridine / CH₂Cl₂ / Ambient temperature

4: 91 percent / Bu₄NF * 3 H₂O / tetrahydrofuran / Ambient temperature

With pyridine; tetrabutyl ammonium fluoride; ammonia; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/hlca.19930760207

upstream raw materials:

N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-5'-<(tritylthio)methyl>-1'a-carbaadenosine

5-norbornene-2-methanol

methyl (1R,2S,4S)-2-(<(tert-butyl)diphenylsilyloxy>methyl)-4-hydroxycyclopentaneacetate

5'-<(acetylthio)methyl>-N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine

Downstream raw materials:

N⁶-benzoyl-2',3',5'-trideoxy-3'-<(methylsulfonyloxy)methyl>-5'-<(tritylthio)methyl>-1'a-carbaadenosine

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