((2R,3R,4R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate

Base Information

• Chemical Name: ((2R,3R,4R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate
• CAS No.: 863329-65-1
• Molecular Formula: C₂₄H₂₁FN₂O₇
• Molecular Weight: 468.438
• European Community (EC) Number: 807-766-2
• DSSTox Substance ID: DTXSID301171912
• Mol file: 863329-65-1.mol

Synonyms:863329-65-1;RO 2433 Dibenzoate;[(2R,3R,4R,5R)-3-Benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-4-methyl-tetrahydrofuran-2-yl]methyl benzoate;(2'R)-2'-Deoxy-2'-fluoro-2'-Methyl-uridine 3',5'-dibenzoate;((2R,3R,4R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate;[(2R,3R,4R,5R)-3-benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-4-methyloxolan-2-yl]methyl benzoate;AMY918;SCHEMBL12202841;DTXSID301171912;AKOS025403879;CS-13088;CS-0009691;P14127;[(2R,3R,4R,5R)-3-Benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-4-methyl-tetrahydrofuran-2-yl]methylbenzoate

Chemical Property of ((2R,3R,4R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate

Chemical Property:

• Melting Point: 256-258℃
• PSA: 116.95000
• Density: 1.42
• LogP: 2.65710
• Water Solubility.: 3.7mg/L
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 468.13327918
• Heavy Atom Count: 34
• Complexity: 837

Purity/Quality:

99.9% ^*data from raw suppliers

RO2433Dibenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C(OC1N2C=CC(=O)NC2=O)COC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)F
• Isomeric SMILES: C[C@]1([C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)COC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)F
• Uses: RO 2433 Dibenzoate is a related compound of RO 2433 (R637200), a deaminated metabolite of β-D-2''-Deoxy-2''-fluoro-2''-C-methylcytidine, an effective inhibitor of hepatitis C virus (HCV) replication in vitro.

Technology Process of ((2R,3R,4R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate

There total 41 articles about ((2R,3R,4R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate 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: 93.0%

(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate (817204-32-3) → (2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate (863329-65-1)

Guidance literature:

With formic acid; In water; at 25 - 100 ℃; for 7.5h;

Reference yield: 90.0%

N4-benzoyl-3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-2'-C-methylcytidine → 3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-2'-C-methyluridine (863329-65-1)

Guidance literature:

With acetic acid; In water; at 110 ℃; for 5h;

Reference yield: 88.0%

3',5'-O-dibenozyl-2'deoxy-2'-fluoro-2'-C-methyl-N4-benzoylcytidine → (2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate (863329-65-1)

Guidance literature:

With water; acetic acid; at 110 ℃; for 20h;

upstream raw materials:

(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate

(2R,3R,4R,5R)-5-acetoxy-2-((benzoyloxy)methyl)-4-fluoro-4-methyl-tetrahydrofuran-3-yl benzoate

((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate

Downstream raw materials:

1-[(2S,3R,4R,5R)-3-fluoro-4-hydroxy-5-hydroxymethyl-3-methyltetrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dione

(S)-2-{[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}-3-methylbutyric acid methyl ester

(S)-2-{(4-bromophenoxy)[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}propionic acid methyl ester

(S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester

Refernces

• 1、 -. "Nucleoside phosphoramidate compound optical isomer and its application". Paragraph 0089-0091. . Retrieved 2018/07/30.
• 2、 Wang, Gang,Lim, Siew Pheng,Chen, Yen-Liang,Hunziker, Jürg,Rao, Ranga,Gu, Feng,Seh, Cheah Chen,Ghafar, Nahdiyah Abdul,Xu, Haoying,Chan, Katherine,Lin, Xiaodong,Saunders, Oliver L.,Fenaux, Martijn,Zhong, Weidong,Shi, Pei-Yong,Yokokawa, Fumiaki. "Structure-activity relationship of uridine-based nucleoside phosphoramidate prodrugs for inhibition of dengue virus RNA-dependent RNA polymerase". . p. 2324 - 2327. Retrieved 2018/05/28.