(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

Base Information

Chemical Name:(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
CAS No.:154230-41-8
Molecular Formula:C₂₅H₂₄N₂O₈
Molecular Weight:480.474
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 6 articles about (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 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: 98.0%

: 154230-40-7
(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 tert-butyl ester

: 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

Guidance literature:: With trifluoroacetic acid;
DOI:10.1021/jo00081a003

Reference yield: 76.0%

: 154230-39-4
(2R,3S,5R)-benzoic acid 5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester

: 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

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In water; acetonitrile; at 20 ℃; for 16h;
DOI:10.1016/j.bmc.2007.05.047

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 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

Guidance literature:: Multi-step reaction with 5 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

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