((2R,3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)tetrahydrothiophen-2-yl)methanol

Base Information

Chemical Name:((2R,3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)tetrahydrothiophen-2-yl)methanol
CAS No.:1203544-73-3
Molecular Formula:C₂₉H₄₆IN₅O₃SSi₂
Molecular Weight:727.857
Hs Code.:

Synonyms:

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Chemical Property of ((2R,3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)tetrahydrothiophen-2-yl)methanol

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Technology Process of ((2R,3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)tetrahydrothiophen-2-yl)methanol

There total 13 articles about ((2R,3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)tetrahydrothiophen-2-yl)methanol 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:

: 1203544-71-1
C₃₆H₅₀IN₅O₄SSi₂

: 1203544-73-3
((2R,3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)tetrahydrothiophen-2-yl)methanol

Guidance literature:: With methanol; sodium methylate; at 20 ℃; for 4h;
DOI:10.1016/j.bmc.2009.10.011

Reference yield:

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

: 1203544-73-3
((2R,3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)tetrahydrothiophen-2-yl)methanol

Guidance literature:: Multi-step reaction with 10 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

8: acetic acid / water / 70 °C / Inert atmosphere

9: pyridine / 5 h / 50 °C / Inert atmosphere

10: sodium methylate / methanol / 4 h / 20 °C / Inert atmosphere

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

Reference yield:

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

: 1203544-73-3
((2R,3S,4R,5R)-3,4-bis((tert-butyldimethylsilyl)oxy)-5-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)tetrahydrothiophen-2-yl)methanol

Guidance literature:: Multi-step reaction with 9 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

7: acetic acid / water / 70 °C / Inert atmosphere

8: pyridine / 5 h / 50 °C / Inert atmosphere

9: sodium methylate / methanol / 4 h / 20 °C / Inert atmosphere

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