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

Base Information

Chemical Name:(2R,3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
CAS No.:154230-43-0
Molecular Formula:C₂₆H₂₆N₂O₈
Molecular Weight:494.501
Hs Code.:

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

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

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

There total 8 articles about (2R,3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-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:

: 546-67-8
lead(IV) tetraacetate

: 154230-41-8
(2S,3S,5R)-3-benzoyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carboxylic acid

: 154230-43-0
(2R,3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

: 154230-42-9
(2S,3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Guidance literature:: With pyridine; In N,N-dimethyl-formamide; at 23 ℃; Yield given. Yields of byproduct given;
DOI:10.1021/jo00081a003

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 154230-43-0
(2R,3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / (i-Pr)2NEt / CH₂Cl₂ / 23 °C

2: 87 percent / Et₃N / CH₂Cl₂ / 23 °C

3: 97 percent / HF-pyridine / tetrahydrofuran / 23 °C

4: 65 percent / CrO₃, pyridine, Ac₂O / CH₂Cl₂; dimethylformamide / 0 - 23 °C

5: 98 percent / CF₃COOH

6: pyridine / dimethylformamide / 23 °C

With pyridine; chromium(VI) oxide; acetic anhydride; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00081a003

Reference yield:

: 101527-40-6
5'-O-tert-butyldiphenylsilylthymidine

: 154230-43-0
(2R,3S,5R)-benzoic acid 2-acetoxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / (i-Pr)2NEt / CH₂Cl₂ / 23 °C

2: 87 percent / Et₃N / CH₂Cl₂ / 23 °C

3: 97 percent / HF-pyridine / tetrahydrofuran / 23 °C

4: 65 percent / CrO₃, pyridine, Ac₂O / CH₂Cl₂; dimethylformamide / 0 - 23 °C

5: 98 percent / CF₃COOH

6: pyridine / dimethylformamide / 23 °C

With pyridine; chromium(VI) oxide; acetic anhydride; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00081a003