(-)-(2R,3R,4R,5S)-5-(6-Amino-9H-purin-9-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate

Base Information

Chemical Name:(-)-(2R,3R,4R,5S)-5-(6-Amino-9H-purin-9-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate
CAS No.:1392126-62-3
Molecular Formula:C₃₅H₄₃N₅O₇SSi
Molecular Weight:705.907
Hs Code.:

Synonyms:(-)-(2R,3R,4R,5S)-5-(6-Amino-9H-purin-9-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate

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Chemical Property of (-)-(2R,3R,4R,5S)-5-(6-Amino-9H-purin-9-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate

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Technology Process of (-)-(2R,3R,4R,5S)-5-(6-Amino-9H-purin-9-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate

There total 4 articles about (-)-(2R,3R,4R,5S)-5-(6-Amino-9H-purin-9-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate 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%

: 904893-24-9
(-)-(2R,3R,4R)-1,3,4-tris(benzyloxy)-5-oxopentan-2-yl methanesulfonate

: 130372-34-8
9-Trimethylsilanyl-9H-purin-6-ylamine

: 1392126-62-3
(-)-(2R,3R,4R,5S)-5-(6-Amino-9H-purin-9-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate

Guidance literature:: With magnesium bromide diethyl etherate; In dichloromethane; acetonitrile; at -20 ℃; for 16h; Inert atmosphere;
DOI:10.1021/jo3012754

Reference yield:

: 158226-97-2
(-)-(2R,3S,4R)-1,3,4-tris(benzyloxy)-5,5-bis(ethylthio)pentan-2-ol

: 1392126-62-3
(-)-(2R,3R,4R,5S)-5-(6-Amino-9H-purin-9-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 2.5 h / -40 - 0 °C / Inert atmosphere

2: 2,6-dimethylpyridine; N-Bromosuccinimide; water / acetone / 0.25 h / 0 °C / Inert atmosphere

3: magnesium bromide diethyl etherate / dichloromethane; acetonitrile / 16 h / -20 °C / Inert atmosphere

With 2,6-dimethylpyridine; N-Bromosuccinimide; water; magnesium bromide diethyl etherate; triethylamine; In dichloromethane; acetone; acetonitrile;
DOI:10.1021/jo3012754

Reference yield:

: 1392126-44-1
(-)-(2R,3R,4R)-1,3,4-tris(benzyloxy)-5,5-bis(ethylthio)pentan-2-yl methanesulfonate

: 1392126-62-3
(-)-(2R,3R,4R,5S)-5-(6-Amino-9H-purin-9-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl methanesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1: 2,6-dimethylpyridine; N-Bromosuccinimide; water / acetone / 0.25 h / 0 °C / Inert atmosphere

2: magnesium bromide diethyl etherate / dichloromethane; acetonitrile / 16 h / -20 °C / Inert atmosphere

With 2,6-dimethylpyridine; N-Bromosuccinimide; water; magnesium bromide diethyl etherate; In dichloromethane; acetone; acetonitrile;
DOI:10.1021/jo3012754