[(2S,3S,4R,5R)-4-acetoxy-3-benzyloxy-2-(benzyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate

Base Information

Chemical Name:[(2S,3S,4R,5R)-4-acetoxy-3-benzyloxy-2-(benzyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate
CAS No.:206055-49-4
Molecular Formula:C₂₉H₃₂N₂O₉
Molecular Weight:552.581
Hs Code.:

Synonyms:[(2S,3S,4R,5R)-4-acetoxy-3-benzyloxy-2-(benzyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate

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Chemical Property of [(2S,3S,4R,5R)-4-acetoxy-3-benzyloxy-2-(benzyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate

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Technology Process of [(2S,3S,4R,5R)-4-acetoxy-3-benzyloxy-2-(benzyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate

There total 8 articles about [(2S,3S,4R,5R)-4-acetoxy-3-benzyloxy-2-(benzyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)tetrahydrofuran-2-yl]methyl 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: 84.7%

: 65-71-4,28806-14-6,691841-57-3
thymin

: 206055-48-3
4-C-acetoxymethyl-1,2-di-O-acetyl-3,5-di-O-benzyl-D-ribofuranose

: 206055-49-4
[(2S,3S,4R,5R)-4-acetoxy-3-benzyloxy-2-(benzyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate

Guidance literature:: thymin; 4-C-acetoxymethyl-1,2-di-O-acetyl-3,5-di-O-benzyl-D-ribofuranose; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 80 ℃; for 1h; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 50 - 80 ℃; for 1h; Inert atmosphere;

Reference yield: 76.0%

: 65-71-4,28806-14-6,691841-57-3
thymin

: Acetic acid (2S,3S,4R,5R)-4,5-diacetoxy-3-benzyloxy-2-benzyloxymethyl-tetrahydro-furan-2-ylmethyl ester

: 206055-49-4
[(2S,3S,4R,5R)-4-acetoxy-3-benzyloxy-2-(benzyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate

Guidance literature:: With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile;
DOI:10.1039/a708608c

Reference yield:

: 63593-03-3
1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

: 206055-49-4
[(2S,3S,4R,5R)-4-acetoxy-3-benzyloxy-2-(benzyloxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)tetrahydrofuran-2-yl]methyl acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH / 1.) DMF, -5 deg C, 1.5 h, 2.) room temperature, 3 h

2: 90 percent / pyridine / 3 h / Ambient temperature

3: 80percent AcOH / 4 h / 90 °C

4: pyridine / 72 h / Ambient temperature

5: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TMS-triflate / 1.) CH₃CN, reflux, 1 h, 2.) 65 deg C, 2 h

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; acetic acid; In pyridine;
DOI:10.1016/S0040-4020(98)00094-5