(2R,3R,4S,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate

Base Information

Chemical Name:(2R,3R,4S,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate
CAS No.:1341075-09-9
Molecular Formula:C₄₃H₄₆FN₅O₈SSi
Molecular Weight:840.017
Hs Code.:

(2R,3R,4S,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate

Synonyms:(2R,3R,4S,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate

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Chemical Property of (2R,3R,4S,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate

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Technology Process of (2R,3R,4S,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate

There total 1 articles about (2R,3R,4S,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate 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: 78.0%

: 700-49-2
2-fluoroadenine

: 212970-74-6
Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

: 1341075-09-9
(2R,3R,4S,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate

Guidance literature:: 2-fluoroadenine; Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 80 ℃; for 1.5h; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 80 ℃; for 3h; Inert atmosphere;

With sodium hydrogencarbonate; In water; acetonitrile; Inert atmosphere;
DOI:10.1016/j.bmc.2011.07.022

Reference yield: 81.0%

: 1341075-09-9
(2R,3R,4S,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate

: 1341075-12-4
9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((tert-butyldiphenylsilyloxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-2-fluoro-9H-purin-6-amine

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; water; at 0 - 25 ℃; for 15h; Inert atmosphere;
DOI:10.1016/j.bmc.2011.07.022

Reference yield:

: 1341075-09-9
(2R,3R,4S,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate

: 1341074-28-9
((1S,3R,4R,7S)-3-(6-amino-2-morpholino-9H-purin-9-yl)-7-(benzyloxy)-2,5-dioxabicyclo[2.2.1]heptan-1-yl)methanol

Guidance literature:: Multi-step reaction with 3 steps

1: sodium hydroxide / tetrahydrofuran; water / 15 h / 0 - 25 °C / Inert atmosphere

2: dimethyl sulfoxide / 24 h / 95 °C / Inert atmosphere

3: pyridine hydrogenfluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With pyridine hydrogenfluoride; sodium hydroxide; In tetrahydrofuran; water; dimethyl sulfoxide;
DOI:10.1016/j.bmc.2011.07.022