ethyl (3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate

Base Information

• Chemical Name: ethyl (3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate
• CAS No.: 877621-26-6
• Molecular Formula: C₃₆H₄₇N₃O₉Si
• Molecular Weight: 693.869

Synonyms:ethyl (3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate

Chemical Property of ethyl (3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate

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Technology Process of ethyl (3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate

There total 1 articles about ethyl (3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate 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: 64.7%

ethyl 2-hydroxyacetate (623-50-7) + (4S,5R)-5-[(1R)-2-[[1-(tert-butyl)-1,1-diphenylsilyl]oxy]-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime + 1-allyl-5-methyl-1H-pyrimidine-2,4-dione (70184-00-8) → ethyl (3S,5S)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate + ethyl (3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate (877621-26-6) + ethyl (3R,5S)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate (877621-25-5) + ethyl (3R,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate (877621-28-8)

Guidance literature:

In toluene; at 80 ℃; for 12h;

DOI:10.1016/j.tet.2005.10.075

Reference yield: 60.0%

ethyl (3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate (877621-26-6) → 1-({(3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl}methyl)-5-methylpyrimidine-2,4(1H,3H)-dione (877621-32-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2005.10.075

upstream raw materials:

ethyl 2-hydroxyacetate

1-allyl-5-methyl-1H-pyrimidine-2,4-dione

Downstream raw materials:

1-({(3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl}methyl)-5-methylpyrimidine-2,4(1H,3H)-dione

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