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

Base Information

• Chemical Name: Acetic acid (2S,3S,4R,5R)-4-acetoxymethyl-4-benzyloxy-5-benzyloxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 858128-98-0
• Molecular Formula: C₂₉H₃₂N₂O₉
• Molecular Weight: 552.581

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

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

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

There total 3 articles about Acetic acid (2S,3S,4R,5R)-4-acetoxymethyl-4-benzyloxy-5-benzyloxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-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:

Acetic acid (3S,4R,5R)-4-acetoxymethyl-4-benzyloxy-5-benzyloxymethyl-2-methoxy-tetrahydro-furan-3-yl ester + thymin (65-71-4,28806-14-6,691841-57-3) → Acetic acid (2S,3S,4R,5R)-4-acetoxymethyl-4-benzyloxy-5-benzyloxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (858128-98-0)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 70 ℃; for 24h;

DOI:10.1021/jo0500380

Reference yield:

methyl 3,5-di-O-benzyl-3-C-(methanesulfonyloxymethyl)-D-ribofuranoside → Acetic acid (2S,3S,4R,5R)-4-acetoxymethyl-4-benzyloxy-5-benzyloxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (858128-98-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / CH₂Cl₂ / -30 - 20 °C

2: 18-crown-6 / dimethylformamide / 3 h / 95 °C

3: N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 24 h / 70 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0500380

Reference yield:

Trifluoro-methanesulfonic acid (3R,4R,5R)-4-benzyloxy-5-benzyloxymethyl-4-methanesulfonyloxymethyl-2-methoxy-tetrahydro-furan-3-yl ester → Acetic acid (2S,3S,4R,5R)-4-acetoxymethyl-4-benzyloxy-5-benzyloxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (858128-98-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 18-crown-6 / dimethylformamide / 3 h / 95 °C

2: N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 24 h / 70 °C

With N,O-bis-(trimethylsilyl)-acetamide; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0500380

upstream raw materials:

thymin

Downstream raw materials:

1-{(1R,2R,4S,5S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-1-hydroxy-3,6-dioxa-bicyclo[3.2.0]hept-4-yl}-5-methyl-1H-pyrimidine-2,4-dione

N1-(3,5-di-O-benzyl-3-C-(methanesulfonyloxymethyl)-α-D-arabinofuranosyl)thymine

(1R,2R,4S,5S)-1-(benzyloxy)-2-[(benzyloxy)methyl]-4-(thymin-1-yl)-3,6-dioxabicyclo[3.2.0]heptane

N1-(3,5-di-O-benzyl-3-C-(hydroxymethyl)-α-D-arabinofuranosyl)thymine

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