((3aS,4R,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methyl benzoate

Base Information

Chemical Name:((3aS,4R,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methyl benzoate
CAS No.:1203544-69-7
Molecular Formula:C₂₇H₂₆IN₅O₄S
Molecular Weight:643.505
Hs Code.:

Synonyms:((3aS,4R,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methyl benzoate

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Chemical Property of ((3aS,4R,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methyl benzoate

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Technology Process of ((3aS,4R,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methyl benzoate

There total 10 articles about ((3aS,4R,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methyl benzoate 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: 88.0%

: 900810-19-7
benzoic acid (3aS,4R,6R,6aR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester

: 696-40-2
3-iodobenzylamine

: 1203544-69-7
((3aS,4R,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methyl benzoate

Guidance literature:: With triethylamine; In ethanol; at 20 ℃; for 24h;
DOI:10.1016/j.bmc.2009.10.011

Reference yield:

: ((3aR,4S,6aR)-2,2-dimethyl-6-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl benzoate

: 1203544-69-7
((3aS,4R,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1: sodium tetrahydroborate / methanol / 3 h / 0 - 20 °C

2: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere

3: sodium sulfide hydrate / N,N-dimethyl-formamide / 15 h / 100 °C / Inert atmosphere

4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -78 °C / Inert atmosphere

5: triethylamine / acetonitrile; 1,2-dichloro-ethane / 96 h / 80 °C / Inert atmosphere

6: triethylamine / ethanol / 24 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; sodium sulfide hydrate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; 5: |Pummerer Sulfoxide Rearrangement;
DOI:10.1021/acs.jmedchem.7b00805

Reference yield:

: 152006-17-2
2,3-O-isopropylidene-L-lyxono-1,4-lactone

: 1203544-69-7
((3aS,4R,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2: sodium tetrahydroborate / methanol / 3 h / 0 - 20 °C

3: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere

4: sodium sulfide hydrate / N,N-dimethyl-formamide / 15 h / 100 °C / Inert atmosphere

5: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -78 °C / Inert atmosphere

6: triethylamine / acetonitrile; 1,2-dichloro-ethane / 96 h / 80 °C / Inert atmosphere

7: triethylamine / ethanol / 24 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; sodium sulfide hydrate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; 6: |Pummerer Sulfoxide Rearrangement;
DOI:10.1021/acs.jmedchem.7b00805