5'-O-(4-Monomethoxytrityl)-3'-nitro-2',3'-dideoxy-2',3'-didehydrothymidine

Base Information

• Chemical Name: 5'-O-(4-Monomethoxytrityl)-3'-nitro-2',3'-dideoxy-2',3'-didehydrothymidine
• CAS No.: 148279-88-3
• Molecular Formula: C₃₀H₂₇N₃O₇
• Molecular Weight: 541.56

Synonyms:5'-O-(4-Monomethoxytrityl)-3'-nitro-2',3'-dideoxy-2',3'-didehydrothymidine

Chemical Property of 5'-O-(4-Monomethoxytrityl)-3'-nitro-2',3'-dideoxy-2',3'-didehydrothymidine

Chemical Property:

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Technology Process of 5'-O-(4-Monomethoxytrityl)-3'-nitro-2',3'-dideoxy-2',3'-didehydrothymidine

There total 1 articles about 5'-O-(4-Monomethoxytrityl)-3'-nitro-2',3'-dideoxy-2',3'-didehydrothymidine 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: 29.0%

methyl vinyl ketone (78-94-4,25038-87-3) + 1-{(2R,3R,5S)-5-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-4-nitro-3-phenylsulfanyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione → 5'-O-(4-Monomethoxytrityl)-3'-nitro-2',3'-dideoxy-2',3'-didehydrothymidine (148279-88-3) + 1-<5-O-(MMTr)-2,3-dideoxy-2-(R)-thiophenyl-3-(S)-(3-oxobutyl)-3-nitro-β-D-pentofuranosyl>thymine (153279-86-8) + 1-<5-O-(MMTr)-2,3-dideoxy-2-(R)-thiophenyl-3-(R)-(3-oxobutyl)-3-nitro-β-D-pentofuranosyl>thymine

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Yields of byproduct given; 0 deg C and 10 min, room t.;

DOI:10.1016/S0040-4020(01)80201-5

Reference yield: 78.0%

thiophenol (108-98-5) + 5'-O-(4-Monomethoxytrityl)-3'-nitro-2',3'-dideoxy-2',3'-didehydrothymidine (148279-88-3) → 1-{(2R,3R,5S)-5-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-4-nitro-3-phenylsulfanyl-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:

With N,N,N',N'-tetramethylguanidine; In acetonitrile; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80201-5

Reference yield: 68.0%

furan (110-00-9) + 5'-O-(4-Monomethoxytrityl)-3'-nitro-2',3'-dideoxy-2',3'-didehydrothymidine (148279-88-3) → 1-<5-O-(MMTr)-2,3-dideoxy-3-nitro-2,3-C-(endo-1,4-dihydrofuran-1,4-yl)-β-D-ribofuranosyl>thymine

Guidance literature:

In toluene; at 70 ℃; for 48h;

DOI:10.1016/S0040-4020(01)91224-4

upstream raw materials:

methyl vinyl ketone

Downstream raw materials:

1-<5-O-(MMTr)-2,3-dideoxy-3-nitro-2,3-C-(endo-2-cyclopentene-1,4-yl)-β-D-ribofuranosyl>thymine

1-<5-O-(MMTr)-2,3-dideoxy-3-nitro-2,3-C-(exo-2-cyclopentene-1,4-yl)-β-D-ribofuranosyl>thymine

1-<5-O-(MMTr)-2,3-dideoxy-2-(R)-thiophenyl-3-(S)-hydroxymethyl-3-nitro-β-D-pentofuranosyl>thymine

1-<5-O-(MMTr)-2,3-dideoxy-2-(R)-thiophenyl-3-(R)-hydroxymethyl-3-nitro-β-D-pentofuranosyl>thymine

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