Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(4-benzyloxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(4-benzyloxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 110085-56-8
• Molecular Formula: C₂₁H₂₄N₂O₇
• Molecular Weight: 416.431

Synonyms:Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(4-benzyloxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Chemical Property of Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(4-benzyloxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

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Technology Process of Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(4-benzyloxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

There total 2 articles about Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(4-benzyloxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 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:

3',5'-diacetylthymidine (6979-97-1,97834-40-7,142405-86-5) → Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(4-benzyloxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (110085-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: DMAP; Et₃N / acetonitrile / 20 h

2: Et₃N

With dmap; triethylamine; In acetonitrile;

DOI:10.1002/anie.200461779

Reference yield:

3',5'-Di-O-acetyl-4-O-<(2,4,6-triisopropylphenyl)sulfonyl>thymidine (119680-05-6) + benzyl alcohol (100-51-6,185532-71-2) → Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(4-benzyloxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (110085-56-8)

Guidance literature:

With triethylamine;

DOI:10.1002/anie.200461779

Reference yield:

Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(4-benzyloxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (110085-56-8) → 4-Benzyloxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidin-2-one (110085-59-1)

Guidance literature:

With ammonia; In methanol; water; at 20 ℃;

DOI:10.1002/anie.200461779

upstream raw materials:

3',5'-Di-O-acetyl-4-O-<(2,4,6-triisopropylphenyl)sulfonyl>thymidine

benzyl alcohol

3',5'-diacetylthymidine

Downstream raw materials:

4-Benzyloxy-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidin-2-one

4-Benzyloxy-1-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidin-2-one

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