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

Base Information

Chemical Name:(2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3-yl acetate
CAS No.:557771-59-2
Molecular Formula:C₂₈H₃₂BrN₅O₄Si
Molecular Weight:610.583
Hs Code.:

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

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

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

There total 4 articles about (2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-((tert-butyldiphenylsilyloxy)methyl)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: 79.5%

: 40635-67-4
acetoxyisobutyryl bromide

: 119898-65-6
(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3,4-diol

: Acetic acid (2R,3R,5R)-5-(6-amino-purin-9-yl)-4-bromo-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester

: 557771-59-2
(2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3-yl acetate

Guidance literature:: With water; In acetonitrile; at 0 ℃; for 5h;
DOI:10.1002/hlca.200390069

Reference yield: 59.0%

: 40635-67-4
acetoxyisobutyryl bromide

: 119898-65-6
(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3,4-diol

: 557771-59-2
(2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3-yl acetate

Guidance literature:: With sodium hydrogencarbonate; In water; acetonitrile; at 0 ℃; for 5.5h; Inert atmosphere;

Reference yield:

: 58-61-7
adenosine

: 557771-59-2
(2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3-yl acetate

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; pyridine / 72 h / 20 °C / Inert atmosphere

2: sodium hydrogencarbonate / acetonitrile; water / 5.5 h / 0 °C / Inert atmosphere

With pyridine; dmap; sodium hydrogencarbonate; In water; acetonitrile;