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

Base Information

• Chemical Name: N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-5'-(mercaptomethyl)-1'a-carbaadenosine
• CAS No.: 149551-12-2
• Molecular Formula: C₃₆H₄₁N₅O₂SSi
• Molecular Weight: 635.905

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

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

Chemical Property:

Purity/Quality:

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

There total 12 articles about N⁶-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-5'-(mercaptomethyl)-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: 69.0%

5'-<(acetylthio)methyl>-N6-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-1'a-carbaadenosine (149654-60-4) → N6-benzoyl-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-5'-(mercaptomethyl)-1'a-carbaadenosine (149551-12-2)

Guidance literature:

With ammonia; In methanol; at 0 ℃; for 0.5h;

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-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-5'-(mercaptomethyl)-1'a-carbaadenosine (149551-12-2)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; sodium hydroxide; borane-THF; Celite; 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-3'-(<(tert-butyl)diphenylsilyloxy>methyl)-2',3',5'-trideoxy-5'-(mercaptomethyl)-1'a-carbaadenosine (149551-12-2)

Guidance literature:

Multi-step reaction with 2 steps

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

With ammonia; In methanol;

DOI:10.1002/hlca.19930760207

upstream raw materials:

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

5-norbornene-2-methanol

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

(1R,4R,5S)-5-(<(tert-butyl)diphenylsilyloxy>methyl)bicyclo<2.2.1>heptan-2-one

Downstream raw materials:

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

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

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

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