1-[(2R,4S,5S)-4-(4-Fluoro-benzylamino)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2R,4S,5S)-4-(4-Fluoro-benzylamino)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 153907-32-5
• Molecular Formula: C₃₆H₃₄FN₃O₄
• Molecular Weight: 591.682

Synonyms:1-[(2R,4S,5S)-4-(4-Fluoro-benzylamino)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property of 1-[(2R,4S,5S)-4-(4-Fluoro-benzylamino)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

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Technology Process of 1-[(2R,4S,5S)-4-(4-Fluoro-benzylamino)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

There total 6 articles about 1-[(2R,4S,5S)-4-(4-Fluoro-benzylamino)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 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: 41.0%

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine (104218-44-2) + para-fluorobenzylamine (140-75-0) → 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)thymine (5964-41-0) + 1-[(2R,4S,5S)-4-(4-Fluoro-benzylamino)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (153907-32-5)

Guidance literature:

In acetonitrile; at 120 ℃; for 18h;

DOI:10.1080/07328319308018565

Reference yield:

1-((2R,4S,5S)-4-{[1-(4-Fluoro-phenyl)-meth-(E)-ylidene]-amino}-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione → 1-[(2R,4S,5S)-4-(4-Fluoro-benzylamino)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (153907-32-5)

Guidance literature:

With sodium tetrahydroborate; In ethanol; water; Yield given;

DOI:10.1080/07328319308018565

Reference yield:

3'-amino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine (124355-25-5) → 1-[(2R,4S,5S)-4-(4-Fluoro-benzylamino)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (153907-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium acetate trihydrate, glacial acetic acid / ethanol; H₂O / 0.08 h / 0 - 5 °C

2: sodium borohydride / ethanol; H₂O

With sodium tetrahydroborate; sodium acetate; acetic acid; In ethanol; water;

DOI:10.1080/07328319308018565

upstream raw materials:

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine

para-fluorobenzylamine

3'-amino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine

4-fluorobenzaldehyde

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