(-)-N-(1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

Base Information

Chemical Name:(-)-N-(1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide
CAS No.:1392126-83-8
Molecular Formula:C₃₂H₃₃N₃O₆
Molecular Weight:555.631
Hs Code.:

Synonyms:(-)-N-(1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

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Chemical Property of (-)-N-(1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

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Technology Process of (-)-N-(1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

There total 5 articles about (-)-N-(1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide 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: 52.0%

: 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

: 1392126-83-8
(-)-N-(1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

Guidance literature:: With aluminum isopropoxide; In dimethyl sulfoxide; at 90 ℃; for 3h; Inert atmosphere;
DOI:10.1021/jo3012754

Reference yield:

: 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

: 1392126-83-8
(-)-N-(1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

Guidance literature:: Multi-step reaction with 2 steps

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

2: aluminum isopropoxide / dimethyl sulfoxide / 3 h / 90 °C / Inert atmosphere

With pyridine; aluminum isopropoxide; In dichloromethane; dimethyl sulfoxide;
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

: 1392126-83-8
(-)-N-(1-((2S,3R,4S,5S)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

Guidance literature:: Multi-step reaction with 6 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

6.1: aluminum isopropoxide / dimethyl sulfoxide / 3 h / 90 °C / Inert atmosphere

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