N²-isobutyryl-2',3',5'-trideoxy-5'-(methoxycarbonyl)-O⁶-<2-(4-nitrophenyl)ethyl>-3'-<(trityloxy)methyl>-1'a-carbaguanosine

Base Information

• Chemical Name: N²-isobutyryl-2',3',5'-trideoxy-5'-(methoxycarbonyl)-O⁶-<2-(4-nitrophenyl)ethyl>-3'-<(trityloxy)methyl>-1'a-carbaguanosine
• CAS No.: 149654-61-5
• Molecular Formula: C₄₅H₄₆N₆O₇
• Molecular Weight: 782.896

Synonyms:N²-isobutyryl-2',3',5'-trideoxy-5'-(methoxycarbonyl)-O⁶-<2-(4-nitrophenyl)ethyl>-3'-<(trityloxy)methyl>-1'a-carbaguanosine

Chemical Property of N²-isobutyryl-2',3',5'-trideoxy-5'-(methoxycarbonyl)-O⁶-<2-(4-nitrophenyl)ethyl>-3'-<(trityloxy)methyl>-1'a-carbaguanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N²-isobutyryl-2',3',5'-trideoxy-5'-(methoxycarbonyl)-O⁶-<2-(4-nitrophenyl)ethyl>-3'-<(trityloxy)methyl>-1'a-carbaguanosine

There total 10 articles about N²-isobutyryl-2',3',5'-trideoxy-5'-(methoxycarbonyl)-O⁶-<2-(4-nitrophenyl)ethyl>-3'-<(trityloxy)methyl>-1'a-carbaguanosine 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: 71.0%

methyl (1R,2S,4S)-4-hydroxy-2-<(trityloxy)methyl>cyclopentaneacetate (149654-55-7) + N2-Isobutyryl-O6-[2-(4-nitrophenylethyl)]guanine (143325-60-4) → N2-isobutyryl-2',3',5'-trideoxy-5'-(methoxycarbonyl)-O6-<2-(4-nitrophenyl)ethyl>-3'-<(trityloxy)methyl>-1'a-carbaguanosine (149654-61-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; 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) → N2-isobutyryl-2',3',5'-trideoxy-5'-(methoxycarbonyl)-O6-<2-(4-nitrophenyl)ethyl>-3'-<(trityloxy)methyl>-1'a-carbaguanosine (149654-61-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / pyridine, Bu₄N(ClO₄) / CH₂Cl₂ / 4.5 h / Ambient temperature

2: 1) (+)-(1R)-α-pinene, BH3-THF, 2) 30percent aq. H2O2, 3N aq. NaOH, NaHSO3

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

4: NaHCO₃, 3-chloroperbenzoic acid / 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

8: 71 percent / PPh₃, diethyl azodicarboxylate / dioxane; tetrahydrofuran / Ambient temperature

With pyridine; sodium hydroxide; borane-THF; Celite; tetrabutylammonium perchlorate; ammonia; dihydrogen peroxide; sodium hydrogencarbonate; 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene; sodium hydrogensulfite; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1002/hlca.19930760207

Reference yield:

trityl chloride (76-83-5) → N2-isobutyryl-2',3',5'-trideoxy-5'-(methoxycarbonyl)-O6-<2-(4-nitrophenyl)ethyl>-3'-<(trityloxy)methyl>-1'a-carbaguanosine (149654-61-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / pyridine, Bu₄N(ClO₄) / CH₂Cl₂ / 4.5 h / Ambient temperature

2: 1) (+)-(1R)-α-pinene, BH3-THF, 2) 30percent aq. H2O2, 3N aq. NaOH, NaHSO3

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

4: NaHCO₃, 3-chloroperbenzoic acid / 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

8: 71 percent / PPh₃, diethyl azodicarboxylate / dioxane; tetrahydrofuran / Ambient temperature

With pyridine; sodium hydroxide; borane-THF; Celite; tetrabutylammonium perchlorate; ammonia; dihydrogen peroxide; sodium hydrogencarbonate; 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene; sodium hydrogensulfite; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1002/hlca.19930760207

upstream raw materials:

methyl (1R,2S,4S)-4-hydroxy-2-<(trityloxy)methyl>cyclopentaneacetate

N²-Isobutyryl-O⁶-[2-(4-nitrophenylethyl)]guanine

5-norbornene-2-methanol

trityl chloride

Downstream raw materials:

[(1R,2S,4R)-4-(6-Hydroxy-2-isobutyrylamino-purin-9-yl)-2-trityloxymethyl-cyclopentyl]-acetic acid methyl ester

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