3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-2-diazo-3-oxo-propionic acid methyl ester

Base Information

• Chemical Name: 3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-2-diazo-3-oxo-propionic acid methyl ester
• CAS No.: 357928-43-9
• Molecular Formula: C₂₆H₂₆N₈O₉
• Molecular Weight: 594.541

Synonyms:3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-2-diazo-3-oxo-propionic acid methyl ester

Chemical Property of 3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-2-diazo-3-oxo-propionic acid methyl ester

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Technology Process of 3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-2-diazo-3-oxo-propionic acid methyl ester

There total 4 articles about 3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-2-diazo-3-oxo-propionic acid methyl ester 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: 86.0%

3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-3-oxo-propionic acid methyl ester (357928-62-2) → 3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-2-diazo-3-oxo-propionic acid methyl ester (357928-43-9)

Guidance literature:

With triethylamine; Methanesulfonyl azide; In dichloromethane; at 20 ℃;

DOI:10.1021/ol015995k

Reference yield:

2',3'-isopropylideneadenosine-5'-carboxylic acid (19234-66-3) → 3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-2-diazo-3-oxo-propionic acid methyl ester (357928-43-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / BOP; 1-hydroxybenzotriazole hydrate / dimethylformamide / 4 h / 20 °C

2: 66 percent / NaHCO₃ / acetonitrile; CH₂Cl₂ / 22 h / 20 °C

3: 50 percent / toluene / 110 °C

4: 86 percent / Et₃N; MsN₃ / CH₂Cl₂ / 20 °C

With sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1-hydroxybenzotriazol-hydrate; triethylamine; Methanesulfonyl azide; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ol015995k

Reference yield:

5'-N-methyl-2',3'-O-isopropylidenecarboxamidoadenosine (39491-51-5) → 3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-2-diazo-3-oxo-propionic acid methyl ester (357928-43-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / NaHCO₃ / acetonitrile; CH₂Cl₂ / 22 h / 20 °C

2: 50 percent / toluene / 110 °C

3: 86 percent / Et₃N; MsN₃ / CH₂Cl₂ / 20 °C

With sodium hydrogencarbonate; triethylamine; Methanesulfonyl azide; In dichloromethane; toluene; acetonitrile;

DOI:10.1021/ol015995k

upstream raw materials:

3-{[(3aS,4S,6R,6aR)-6-(6-Benzyloxycarbonylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl]-methyl-amino}-3-oxo-propionic acid methyl ester

2',3'-isopropylideneadenosine-5'-carboxylic acid

5'-N-methyl-2',3'-O-isopropylidenecarboxamidoadenosine

[9-((3aR,4R,6S,6aS)-2,2-Dimethyl-6-methylcarbamoyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-carbamic acid benzyl ester

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