Shandong Mopai Biotechnology Co., LTD is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemicals. W
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inquiryNewCan Biotech Limited was established in 2021 and is primarily engaged in the research, development, production, and sales of sugars, nucleosides, nucleotides, phosphorylated monomers, as well as next-generation antiviral and antitumor drug intermed
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inquiryItems Standard Result Appearance A white or off-white crystalline powder White crystalline powder Solubility
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inquiryProduct Description Product website: http://www.finerchem.com/pro01en/id/1023.html Product Name 2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine CAS No.
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inquiryhebei yanxi chemical co., LTD who registered capital of 10 million yuan, nearly to $2 million, we have a pharmaceutical raw materials factory production of pharmaceutical raw materials, and a reagent r&d center, and we do research and developm
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inquiryWe can provide GMP validation service that complies with SFDA, FDA, WHO and EU EMPA.Excellent registration team could help us easlily to register our products in different countries.If you and your customer are interested in some products or need CMO
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inquiryUnique advantages for 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine Cas161599-46-8 Guaranteed the purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:White powder Storage:cool dry pla
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inquiry2',3'-di-O-acetyl-5'-deoxy-5-fluorocytidine 2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-D-cytidine[CAS:161599-46-8] HANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contra
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inquiryThe above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
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inquiry1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s
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inquiryName:2',3'-DI-O-ACETYL-5'-DEOXY-5-FLUOROCYTIDINE CAS:161599-46-8 Grade:For chemical industry, scientific research and export Product Quality 12 years of chemical raw materials Mature operation of the industry System stability Data
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inquiryTIANFUCHEM--161599-46-8-- 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine in stock Our company was built in 2009 with an ISO certificate.In the past 10 years, we have grown up as a famous fine chemicals supplier in China And we
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inquiryAbout Product Details Item Specification Test Results Appearance White crystalline powder Conform
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inquiryOur Advantage Rich Experience Our products are sold all over Europe,North&South America, Sino-East, Asia and pacific area as well as Africa,we establish long term. Quality service Company cooperates with research institutes. We strictly con
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inquiryProduct name 2’,3’-Di-O-Acetyl-5’-Deoxy-5-Fluoro Cytidine Synonyms 5'-Deoxy-2',3'-di-O-acetyl-5-fluorocytidine CAS N
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inquiry1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:White Crystalline Powder Storage:Store in sealed conta
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inquiryHanways chempharm is a specialized company concentrating on the R&D, production, marketing and technical service of APIs and pharmaceutical intermediates. The marketing department is located in Wuhan. We have two GMP facilities in Hubei Pr
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inquiryProduct Name: 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine CAS: 161599-46-8 MF: C13H16FN3O6 MW: 329.28 EINECS: 605-260-4 Mol File: 161599-46-8.mol 2',3'-Di-O-acetyl-5'-deoxy-5-fuluro-D-cytidine Structure
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inquiryHello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
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inquiryFlucytosine
1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at 10 - 20℃; for 4h; Solvent; | 88.6% |
Stage #1: Flucytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 3h; Reflux; Stage #2: 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose With tin(IV) chloride In dichloromethane at -5℃; Inert atmosphere; Heating; | 83.6% |
Stage #1: Flucytosine With trifluorormethanesulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 2h; Reflux; Stage #2: 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose With trifluorormethanesulfonic acid at 20 - 55℃; | 80% |
di-O-acetyl-5-deoxy-ξ-D-ribofuranosyl chloride
2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Stage #1: di-O-acetyl-5-deoxy-ξ-D-ribofuranosyl chloride; 2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine In 1,2-dichloro-ethane for 4h; Inert atmosphere; Schlenk technique; Reflux; Stage #2: With water Inert atmosphere; Schlenk technique; | 86% |
5-fluoro-2-trimethylsilanyloxy-pyrimidin-4-ylamine
1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With tin(IV) chloride; sodium hydrogencarbonate In dichloromethane; water at 0 - 20℃; for 0.5h; | 78.4% |
5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Stage #1: 5-fluorocytosine With 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 4h; Autoclave; Reflux; Industrial scale; Stage #2: 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose With tin(IV) chloride In dichloromethane at 2 - 20℃; for 12h; Industrial scale; | 74% |
5'-deoxy-5-fluorocytidine
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With acetic anhydride In pyridine; water |
5'-deoxy-2',3'-di-O-acetyl-5-fluoro-N4-((5-nitrothien-2-yl)methoxycarbonyl)cytidine
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
In water; isopropyl alcohol G-values; Irradiation; |
acetic anhydride
5'-deoxy-5-fluorocytidine
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With pyridine at 0℃; for 3h; | |
With pyridine at 0℃; for 3h; |
Flucytosine
5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Stage #1: Flucytosine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In toluene at 110℃; for 0.5h; Stage #2: 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose With tin(IV) chloride In dichloromethane at 0 - 30℃; Stage #3: With water; sodium hydrogencarbonate In dichloromethane for 2h; |
5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose
5-fluoro-2-trimethylsilanyloxy-pyrimidin-4-ylamine
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
tin(IV) chloride In dichloromethane at 0℃; for 2h; |
2',3',5'-tri-O-acetyl-5-fluorocytidine
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pyridine / dichloromethane / 1.5 h / 0 °C 2: alcalase enzyme cross linked aggregate / ethanol / 100 h / 20 °C / Enzymatic reaction 3: carbon tetrabromide / dichloromethane / 3 h / 20 °C / Inert atmosphere 4: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / Reflux View Scheme |
N1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-fluoro-N4-(n-pentyloxycarbonyl)cytosine
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: alcalase enzyme cross linked aggregate / ethanol / 100 h / 20 °C / Enzymatic reaction 2: carbon tetrabromide / dichloromethane / 3 h / 20 °C / Inert atmosphere 3: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / Reflux View Scheme |
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: carbon tetrabromide / dichloromethane / 3 h / 20 °C / Inert atmosphere 2: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / tetrahydrofuran / Reflux View Scheme |
A
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
B
N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In tetrahydrofuran Reflux; Overall yield = 45 %; |
methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / dimethyl sulfoxide 2: sulfuric acid / water / 80 - 90 °C / Large scale 3: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale 4: tin(IV) chloride / dichloromethane / 5 - 10 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; acetic acid / dimethyl sulfoxide / 20 h / 80 - 85 °C 2.1: sulfuric acid / 17 h / 80 - 90 °C 2.2: 16 h / 20 °C 3.1: 1,1,1,3,3,3-hexamethyl-disilazane / toluene / 100 °C 3.2: 2.33 h / 20 °C / Cooling with ice View Scheme |
methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sulfuric acid / water / 80 - 90 °C / Large scale 2: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale 3: tin(IV) chloride / dichloromethane / 5 - 10 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sulfuric acid / 17 h / 80 - 90 °C 1.2: 16 h / 20 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane / toluene / 100 °C 2.2: 2.33 h / 20 °C / Cooling with ice View Scheme |
(2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale 2: tin(IV) chloride / dichloromethane / 5 - 10 °C View Scheme |
2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine
1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane at 5 - 10℃; | |
With tin(IV) chloride In dichloromethane at -1 - 10℃; Temperature; Inert atmosphere; | 31 g |
β-D-ribofuranose
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: sulfuric acid / 0 - 20 °C 2: triethylamine / dichloromethane / 0 - 20 °C 3: sodium tetrahydroborate; lithium chloride / diethylene glycol dimethyl ether / 20 h / 80 - 90 °C 4: sulfuric acid / water / 80 - 90 °C / Large scale 5: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale 6: tin(IV) chloride / dichloromethane / 5 - 10 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sulfuric acid; tin(II) chloride dihdyrate / 40 - 45 °C 2.1: pyridine / dichloromethane / 20 h / 0 - 5 °C 3.1: sodium tetrahydroborate; acetic acid / dimethyl sulfoxide / 20 h / 80 - 85 °C 4.1: sulfuric acid / 17 h / 80 - 90 °C 4.2: 16 h / 20 °C 5.1: 1,1,1,3,3,3-hexamethyl-disilazane / toluene / 100 °C 5.2: 2.33 h / 20 °C / Cooling with ice View Scheme |
((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: sodium tetrahydroborate; lithium chloride / diethylene glycol dimethyl ether / 20 h / 80 - 90 °C 3: sulfuric acid / water / 80 - 90 °C / Large scale 4: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale 5: tin(IV) chloride / dichloromethane / 5 - 10 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: pyridine / dichloromethane / 20 h / 0 - 5 °C 2.1: sodium tetrahydroborate; acetic acid / dimethyl sulfoxide / 20 h / 80 - 85 °C 3.1: sulfuric acid / 17 h / 80 - 90 °C 3.2: 16 h / 20 °C 4.1: 1,1,1,3,3,3-hexamethyl-disilazane / toluene / 100 °C 4.2: 2.33 h / 20 °C / Cooling with ice View Scheme |
1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-β-D-ribofuranoside
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium tetrahydroborate; lithium chloride / diethylene glycol dimethyl ether / 20 h / 80 - 90 °C 2: sulfuric acid / water / 80 - 90 °C / Large scale 3: triethylamine; dmap / 4 h / -5 - 5 °C / Large scale 4: tin(IV) chloride / dichloromethane / 5 - 10 °C View Scheme |
(3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 1-ethylpiperidine hypophosphite; di-isopropyl azodicarboxylate; triethylamine / 1,4-dioxane / Reflux; Inert atmosphere 2.1: sulfuric acid / water / 2 h / Reflux 2.2: 20 h / 20 °C 3.1: tin(IV) chloride; sodium hydrogencarbonate / water; dichloromethane / 0.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: hydrogen; triethylamine / palladium on activated charcoal / methanol / 24 h / 20 °C / Inert atmosphere 2: hydrogenchloride; water / 2 h / Reflux 3: pyridine / 24 h / 20 °C 4: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme |
1-O-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sulfuric acid / water / 2 h / Reflux 1.2: 20 h / 20 °C 2.1: tin(IV) chloride; sodium hydrogencarbonate / water; dichloromethane / 0.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: hydrogenchloride; water / 2 h / Reflux 2: pyridine / 24 h / 20 °C 3: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme |
D-Ribose
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: hydrogenchloride / water / 3 h / Reflux 2.1: triethylamine / dichloromethane / 4 h / 0 - 5 °C 3.1: sodium iodide / acetonitrile / 12 h / Reflux 4.1: 1-ethylpiperidine hypophosphite; di-isopropyl azodicarboxylate; triethylamine / 1,4-dioxane / Reflux; Inert atmosphere 5.1: sulfuric acid / water / 2 h / Reflux 5.2: 20 h / 20 °C 6.1: tin(IV) chloride; sodium hydrogencarbonate / water; dichloromethane / 0.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 7 steps 1: hydrogenchloride / water / 2 h / Reflux 2: pyridine / 18 h / 20 °C 3: sodium iodide / butanone / 24 h / Reflux 4: hydrogen; triethylamine / palladium on activated charcoal / methanol / 24 h / 20 °C / Inert atmosphere 5: hydrogenchloride; water / 2 h / Reflux 6: pyridine / 24 h / 20 °C 7: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme |
methyl 2,3-O-isopropylidene-D-ribofuranoside
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 4 h / 0 - 5 °C 2.1: sodium iodide / acetonitrile / 12 h / Reflux 3.1: 1-ethylpiperidine hypophosphite; di-isopropyl azodicarboxylate; triethylamine / 1,4-dioxane / Reflux; Inert atmosphere 4.1: sulfuric acid / water / 2 h / Reflux 4.2: 20 h / 20 °C 5.1: tin(IV) chloride; sodium hydrogencarbonate / water; dichloromethane / 0.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 6 steps 1: pyridine / 18 h / 20 °C 2: sodium iodide / butanone / 24 h / Reflux 3: hydrogen; triethylamine / palladium on activated charcoal / methanol / 24 h / 20 °C / Inert atmosphere 4: hydrogenchloride; water / 2 h / Reflux 5: pyridine / 24 h / 20 °C 6: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme |
((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium iodide / acetonitrile / 12 h / Reflux 2.1: 1-ethylpiperidine hypophosphite; di-isopropyl azodicarboxylate; triethylamine / 1,4-dioxane / Reflux; Inert atmosphere 3.1: sulfuric acid / water / 2 h / Reflux 3.2: 20 h / 20 °C 4.1: tin(IV) chloride; sodium hydrogencarbonate / water; dichloromethane / 0.5 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: sodium iodide / butanone / 24 h / Reflux 2: hydrogen; triethylamine / palladium on activated charcoal / methanol / 24 h / 20 °C / Inert atmosphere 3: hydrogenchloride; water / 2 h / Reflux 4: pyridine / 24 h / 20 °C 5: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme |
5-O-deoxy-D-ribofuranose
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / 24 h / 20 °C 2: tin(IV) chloride / dichloromethane / 2 h / 0 °C View Scheme |
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
5'-deoxy-5-fluorocytidine
Conditions | Yield |
---|---|
With ammonia In methanol; water at 45 - 55℃; Product distribution / selectivity; | 95% |
With methanol; diethylamine at 20 - 50℃; for 2h; Inert atmosphere; | 80% |
With methanol; diethylamine at 55℃; for 2h; |
pentyl chloroformate
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
Conditions | Yield |
---|---|
With potassium phosphate In dichloromethane; isopropyl alcohol at 0 - 25℃; for 4h; Reagent/catalyst; Inert atmosphere; | 94.2% |
With pyridine In dichloromethane at 0℃; for 1h; | 93% |
With dmap; potassium carbonate In dichloromethane at 5℃; for 0.75h; Temperature; Solvent; Reagent/catalyst; | 90.6% |
pentan-1-ol
1,1'-carbonyldiimidazole
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 4h; | 91.6% |
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -15 - 20℃; for 2h; | 85% |
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; | 84.1% |
neopentyl chloroformate
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
5'-deoxy-5-fluoro-N4-(neopentyloxycarbonyl)-cytidine
Conditions | Yield |
---|---|
With pyridine; sodium hydroxide; sodium carbonate In methanol; ethanol; dichloromethane | 84% |
pentyl chloroformate
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
capecitabine
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone at 30℃; for 5h; Green chemistry; | 82% |
Stage #1: pentyl chloroformate; (2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate With pyridine In dichloromethane at 0℃; for 1h; Stage #2: With sodium hydroxide In ethanol; water at -5 - 0℃; for 0.233333h; | 80.2% |
Multi-step reaction with 2 steps 1: dichloromethane 2: sodium hydroxide / methanol View Scheme | |
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 1 h / 0 °C 2: sodium methylate / methanol / 1 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium phosphate / isopropyl alcohol; dichloromethane / 4 h / 0 - 25 °C / Inert atmosphere 2: sodium hydroxide / methanol; water / 1 h / -10 - 5 °C / Autoclave View Scheme |
pentyl chloroformate
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone at 30℃; for 1h; Flow reactor; | 35% |
n-hexyl chloroformate
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(5-fluoro-4-hexyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; Acylation; |
n-heptyl chloroformate
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; Acylation; |
octyl chloroformate
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(5-fluoro-4-octyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; Acylation; |
chloroformic acid n-nonyl ester
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; Acylation; |
3,5-dichlorobenzoyl chloride
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; Acylation; |
chloroformic acid ethyl ester
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; Acylation; |
3,4,5-Trimethoxybenzoyl chloride
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[5-fluoro-2-oxo-4-(3,4,5-trimethoxy-benzoylamino)-2H-pyrimidin-1-yl]-5-methyl-tetrahydro-furan-3-yl ester
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; Acylation; |
3,5-dimethoxybenzoyl chloride
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; Acylation; |
methyl chloroformate
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; Acylation; |
carbonochloridic acid, butyl ester
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-butoxycarbonylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; Acylation; |
3,5-dimethylbenzoyl chloride
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; Acylation; |
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
propoxycarbonyl chloride
Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(5-fluoro-2-oxo-4-propoxycarbonylamino-2H-pyrimidin-1-yl)-5-methyl-tetrahydro-furan-3-yl ester
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; Acylation; |
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
5'-deoxy-5-fluoro-N4-(3,4,5-trimethoxybenzoyl)cytidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / -20 - 20 °C 2: NaOH / methanol; H2O / -20 - -5 °C View Scheme |
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / -20 - 20 °C 2: NaOH / methanol; H2O / -20 - -5 °C View Scheme |
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / -20 - 20 °C 2: NaOH / methanol; H2O / -20 - -5 °C View Scheme |
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / -20 - 20 °C 2: NaOH / methanol; H2O / -20 - -5 °C View Scheme |
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / -20 - 20 °C 2: NaOH / methanol; H2O / -20 - -5 °C View Scheme |
(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate
capecitabine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1311 g / pyridine / CH2Cl2 / -20 - 20 °C 2: 170 g / NaOH / methanol; H2O / -20 - -5 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 20 - 30 °C / Inert atmosphere 2: sodium hydroxide / acetone / 2 h / -15 - 10 °C View Scheme |
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