(-)-(2R,3R,4R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate

Base Information

Chemical Name:(-)-(2R,3R,4R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate
CAS No.:1392126-73-6
Molecular Formula:C₄₁H₄₆N₄O₁₁SSi
Molecular Weight:830.988
Hs Code.:

Synonyms:(-)-(2R,3R,4R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate

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Chemical Property of (-)-(2R,3R,4R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate

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Technology Process of (-)-(2R,3R,4R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate

There total 5 articles about (-)-(2R,3R,4R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate 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: 77.0%

: 1392126-70-3
(-)-(2R,3R,4R,5S)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate

: 108-24-7
acetic anhydride

: 1392126-73-6
(-)-(2R,3R,4R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate

Guidance literature:: With pyridine; In dichloromethane; at 0 - 25 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jo3012754

Reference yield:

: 16838-89-4,17073-88-0,60933-68-8,60933-69-9,73068-66-3,89361-52-4,89615-42-9,89615-45-2,96192-07-3
2,3,5-tri-O-benzyl-D-lyxofuranoside

: 1392126-73-6
(-)-(2R,3R,4R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / hexane; tetrahydrofuran; benzene / 2 h / 0 - 25 °C / Inert atmosphere

1.2: 2 h / 0 - 100 °C

2.1: triethylamine; dmap / dichloromethane / 16 h / 0 - 50 °C / Inert atmosphere

3.1: ozone / dichloromethane / 0.67 h / -78 °C

3.2: 0.5 h / 25 °C

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

5.1: pyridine / dichloromethane / 2 h / 0 - 25 °C / Inert atmosphere

With pyridine; dmap; n-butyllithium; magnesium bromide diethyl etherate; ozone; triethylamine; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; benzene; 1.1: |Wittig-Horner Reaction / 1.2: |Wittig-Horner Reaction;
DOI:10.1021/jo3012754

Reference yield:

: 201290-06-4
3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enitol

: 1392126-73-6
(-)-(2R,3R,4R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3,4-tris(benzyloxy)-5-((trimethylsilyl)oxy)pentan-2-yl 4-nitrobenzenesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine; dmap / dichloromethane / 16 h / 0 - 50 °C / Inert atmosphere

2.1: ozone / dichloromethane / 0.67 h / -78 °C

2.2: 0.5 h / 25 °C

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

4.1: pyridine / dichloromethane / 2 h / 0 - 25 °C / Inert atmosphere

With pyridine; dmap; magnesium bromide diethyl etherate; ozone; triethylamine; In dichloromethane; acetonitrile;
DOI:10.1021/jo3012754