[(3aR,4R,6R,6aR)-6-(6-amino-2-phenyl-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl sulfamate

Base Information

Chemical Name:[(3aR,4R,6R,6aR)-6-(6-amino-2-phenyl-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl sulfamate
CAS No.:939794-87-3
Molecular Formula:C₁₉H₂₂N₆O₆S
Molecular Weight:462.486
Hs Code.:

Synonyms:[(3aR,4R,6R,6aR)-6-(6-amino-2-phenyl-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl sulfamate

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Chemical Property of [(3aR,4R,6R,6aR)-6-(6-amino-2-phenyl-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl sulfamate

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Technology Process of [(3aR,4R,6R,6aR)-6-(6-amino-2-phenyl-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl sulfamate

There total 3 articles about [(3aR,4R,6R,6aR)-6-(6-amino-2-phenyl-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl sulfamate 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: 66.0%

: 144456-15-5
2-phenyl-9-β-(2′,3′-O-isopropylidene-D-ribofuranosyl)adenine

: 939794-87-3
[(3aR,4R,6R,6aR)-6-(6-amino-2-phenyl-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl sulfamate

Guidance literature:: 2-phenyl-9-β-(2′,3′-O-isopropylidene-D-ribofuranosyl)adenine; With sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; at 0 ℃; for 0.5h; Inert atmosphere;

With sulphamoyl chloride; In tetrahydrofuran; 1,2-dimethoxyethane; at 20 ℃; for 16h; Inert atmosphere;
DOI:10.1021/jm800567v

Reference yield:

: 146-77-0
2-Chloroadenosine

: 939794-87-3
[(3aR,4R,6R,6aR)-6-(6-amino-2-phenyl-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl sulfamate

Guidance literature:: Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / 20 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; tetrahydrofuran / 12 h / Reflux

3: sulphamoyl chloride / N,N-dimethyl acetamide / 3 h / 0 - 20 °C / Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulphamoyl chloride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl acetamide; water; 2: |Suzuki Coupling;
DOI:10.1021/acs.jmedchem.9b01131

Reference yield:

: 24639-06-3
((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

: 939794-87-3
[(3aR,4R,6R,6aR)-6-(6-amino-2-phenyl-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl sulfamate

Guidance literature:: Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; tetrahydrofuran / 12 h / Reflux

2: sulphamoyl chloride / N,N-dimethyl acetamide / 3 h / 0 - 20 °C / Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulphamoyl chloride; potassium carbonate; In tetrahydrofuran; N,N-dimethyl acetamide; water; 1: |Suzuki Coupling;
DOI:10.1021/acs.jmedchem.9b01131