Name: 10578-79-7|N4-Methylcytidine|98%
Brand: Ambeed
SKU: A192906
Price: 70.0 USD
Availability: InStock
Rating: 99 (28 reviews)

1
[ 15049-50-0 ]
[ 74-89-5 ]
[ 10578-79-7 ]

Reference： [1]Fox et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 178,187]

2
[ 10578-79-7 ]
[ 58501-79-4 ]

Yield	Reaction Conditions	Operation in experiment
	With water; trichlorophosphate In ethyl acetate

Reference： [1]Kanai; Ichino; Hoshi [Journal of Medicinal Chemistry, 1974, vol. 17, # 10, p. 1076 - 1078]

3
[ 593-51-1 ]
[ 108324-69-2 ]
[ 10578-79-7 ]
[ 111426-20-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 20℃; half-life;

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

4
[ 593-51-1 ]
[ 108324-70-5 ]
[ 10578-79-7 ]
[ 111426-20-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 20℃; half-life;

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

5
[ 593-51-1 ]
3-[1-((2R,3R,4R,5R)-3,4-Diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yloxy]-1-methyl-pyridinium; iodide [ No CAS ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; triethylamine 1.) ethanol, 20 deg C, 10 min; Yield given. Multistep reaction;

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

6
[ 593-51-1 ]
3-[1-((2R,3R,4R,5R)-3,4-Diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yloxy]-1-methyl-pyridinium; iodide [ No CAS ]
[ 10578-79-7 ]
[ 111426-20-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 20℃; half-life;

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

7
[ 593-51-1 ]
5-[1-((2R,3R,4R,5R)-3,4-Diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yloxy]-1,2-dimethyl-pyridinium; iodide [ No CAS ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; triethylamine 1.) ethanol, 20 deg C, 10 min; Yield given. Multistep reaction;

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

8
[ 593-51-1 ]
5-[1-((2R,3R,4R,5R)-3,4-Diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yloxy]-1,2-dimethyl-pyridinium; iodide [ No CAS ]
[ 10578-79-7 ]
[ 111426-20-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 20℃; half-life;

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

9
[ 77312-41-5 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; formic acid 1.) glyme, 85 deg C, 2 h, 2.) water, room temp.; Yield given. Multistep reaction;

Reference： [1]Kemal, Oeznur; Reese, Colin B. [Synthesis, 1980, # 12, p. 1025 - 1028]

10
[ 107-71-1 ]
[ 65-46-3 ]
[ 10578-79-7 ]
[ 2140-64-9 ]
[ 2140-61-6 ]

Reference： [1]Journal of Organic Chemistry,1980,vol. 45,p. 2373 - 2377

11
[ 111426-20-1 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With ammonia In methanol at 20℃;
90%	With ammonia In dichloromethane at 25℃;
	With ammonia In methanol at 25℃; for 24h; Yield given;

Reference： [1]Mahto, Santosh K.; Chow, Christine S. [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 19, p. 8795 - 8800]
[2]Saladino, Raffaele; Mincione, Enrico; Crestini, Claudia; Mezzetti, Maurizio [Tetrahedron, 1996, vol. 52, # 19, p. 6759 - 6780]
[3]Saladino, Raffaele; Crestini, Claudia; Bernini, Roberta; Frachey, Giuseppe; Mincione, Enrico [Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3053 - 3054]

12
2',3',5'-tri-O-benzoyl-N⁴-methylcytidine [ No CAS ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With ammonia In methanol Ambient temperature;

Reference： [1]Grasby; Singh; Karn; Gait [Nucleosides and Nucleotides, 1995, vol. 14, # 3-5, p. 1129 - 1132]

13
[ 74-89-5 ]
[ 189005-88-7 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	In ethanol for 1.5h; Ambient temperature;

Reference： [1]Miah, Anwar; Reese, Colin B.; Song, Quanlai [Nucleosides and Nucleotides, 1997, vol. 16, # 1-2, p. 53 - 65]

Yield	Reaction Conditions	Operation in experiment
	With water-d2 at 363.2℃; deuteration of C₅ in acetic buffer;
	With hydrogenchloride at 90.1℃; first-order rate constants for the hydrolysis and deamination; various conditions (acetic acid and triethanolamine buffers); rate constant for the buffer-catalysed deamination;

Yield	Reaction Conditions	Operation in experiment
	Cytidin, Methylammoniumacetat;
	N⁴-Methyl-2-thio-cytidin, 1.) CH3I, 60grad, 2.) NaOH;
	entspr. Thioverb., 1.) Methylamin, 2.) Deacetylierung;

	entspr. Thioverb., 1.) Methylamin, 2.) Deacylierung;
		claim 1 wherein the compound is ... 5-Fluoro-4-methylthio-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one, 5-Methyl-4-methylthio-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one, 3'-Azido-2',3'-dideoxy-5-methylcytidine, 1-(3-Deoxy-β-L-threo-pentofuranosyl)-5-fluorocytosine, 4-Methylamino-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one, 5-Fluoro-4-methylamino-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one, 4-(1-Pyrrolyl)-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one, 1-(2-Deoxy-2,2-difluoro-β-D-erythropentofuranosyl)cytosine, ...

16
[ 17331-14-5 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate In N,N-dimethyl-formamide at 20℃; for 2h;

Reference： [1]Zhang, Jianxing; Chang, Hui-Min; Kane, Robert R. [Synlett, 2001, # 5, p. 643 - 645]

17
[ 58-96-8 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: triethylamine; acetonitrile / 1 h / Ambient temperature; other reagent 2: POCl₃ / acetonitrile / 0.25 h / 0 °C 3: acetonitrile / 3 h / 0 °C 4: 1.62 g / acetic acid; methanol / 5 h / Ambient temperature 5: 97 percent / ethanol / 1.5 h / Ambient temperature
	Multi-step reaction with 3 steps 1: pyridine 2: P₂S₅

Reference： [1]Miah, Anwar; Reese, Colin B.; Song, Quanlai [Nucleosides and Nucleotides, 1997, vol. 16, # 1-2, p. 53 - 65]
[2]Fox et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 178,187]

18
1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-4-chloro-1H-pyrimidin-2-one [ No CAS ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: acetonitrile / 3 h / 0 °C 2: 1.62 g / acetic acid; methanol / 5 h / Ambient temperature 3: 97 percent / ethanol / 1.5 h / Ambient temperature

Reference： [1]Miah, Anwar; Reese, Colin B.; Song, Quanlai [Nucleosides and Nucleotides, 1997, vol. 16, # 1-2, p. 53 - 65]

19
1-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-4-(4-nitro-phenoxy)-1H-pyrimidin-2-one [ No CAS ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.62 g / acetic acid; methanol / 5 h / Ambient temperature 2: 97 percent / ethanol / 1.5 h / Ambient temperature

Reference： [1]Miah, Anwar; Reese, Colin B.; Song, Quanlai [Nucleosides and Nucleotides, 1997, vol. 16, # 1-2, p. 53 - 65]

20
[ 10457-16-6 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: POCl₃ / acetonitrile / 0.25 h / 0 °C 2: acetonitrile / 3 h / 0 °C 3: 1.62 g / acetic acid; methanol / 5 h / Ambient temperature 4: 97 percent / ethanol / 1.5 h / Ambient temperature

Reference： [1]Miah, Anwar; Reese, Colin B.; Song, Quanlai [Nucleosides and Nucleotides, 1997, vol. 16, # 1-2, p. 53 - 65]

21
[ 55003-25-3 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 64 percent / dimethyldioxirane / CH₂Cl₂; acetone / 25 °C 2: 90 percent / 2N methanol. NH₃ / CH₂Cl₂ / 25 °C
	Multi-step reaction with 2 steps 1: dimethyldioxirane / CH₂Cl₂; acetone / 25 °C 2: ammonia / methanol / 24 h / 25 °C

Reference： [1]Saladino, Raffaele; Mincione, Enrico; Crestini, Claudia; Mezzetti, Maurizio [Tetrahedron, 1996, vol. 52, # 19, p. 6759 - 6780]
[2]Saladino, Raffaele; Crestini, Claudia; Bernini, Roberta; Frachey, Giuseppe; Mincione, Enrico [Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3053 - 3054]

22
[ 108782-91-8 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 5 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

23
[ 108324-69-2 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetonitrile / 8 h / 20 °C 2: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

24
[ 108324-70-5 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetonitrile / 8 h / 20 °C 2: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

25
[ 111426-26-7 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 5 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

26
[ 111426-23-4 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 5 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

27
[ 111426-25-6 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 5 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

28
[ 111426-24-5 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 5 steps 1: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 2: pyridine / 1 h / 20 °C 3: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 4: acetonitrile / 8 h / 20 °C 5: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

29
4-(2-Oxo-2H-pyridin-1-yl)-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-trimethylsilanyloxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidin-2-one [ No CAS ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 2: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 3: pyridine / 1 h / 20 °C 4: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 5: acetonitrile / 8 h / 20 °C 6: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 6 steps 1: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 2: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 3: pyridine / 1 h / 20 °C 4: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 5: acetonitrile / 8 h / 20 °C 6: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

30
4-(Pyridin-3-yloxy)-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-trimethylsilanyloxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidin-2-one [ No CAS ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 2: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 3: pyridine / 1 h / 20 °C 4: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 5: acetonitrile / 8 h / 20 °C 6: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 6 steps 1: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 2: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 3: pyridine / 1 h / 20 °C 4: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 5: acetonitrile / 8 h / 20 °C 6: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

31
4-(Pyridin-2-ylsulfanyl)-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-trimethylsilanyloxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidin-2-one [ No CAS ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 2: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 3: pyridine / 1 h / 20 °C 4: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 5: acetonitrile / 8 h / 20 °C 6: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 6 steps 1: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 2: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 3: pyridine / 1 h / 20 °C 4: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 5: acetonitrile / 8 h / 20 °C 6: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

32
4-(6-Methyl-pyridin-2-yloxy)-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-trimethylsilanyloxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidin-2-one [ No CAS ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 2: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 3: pyridine / 1 h / 20 °C 4: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 5: acetonitrile / 8 h / 20 °C 6: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 6 steps 1: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 2: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 3: pyridine / 1 h / 20 °C 4: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 5: acetonitrile / 8 h / 20 °C 6: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

33
4-(6-Methyl-pyridin-3-yloxy)-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-trimethylsilanyloxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidin-2-one [ No CAS ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 2: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 3: pyridine / 1 h / 20 °C 4: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 5: acetonitrile / 8 h / 20 °C 6: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 6 steps 1: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 2: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 3: pyridine / 1 h / 20 °C 4: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 5: acetonitrile / 8 h / 20 °C 6: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

34
[ 415903-48-9 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 3: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 4: pyridine / 1 h / 20 °C 5: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 6: acetonitrile / 8 h / 20 °C 7: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 7 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 3: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 4: pyridine / 1 h / 20 °C 5: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 6: acetonitrile / 8 h / 20 °C 7: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 7 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 3: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 4: pyridine / 1 h / 20 °C 5: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 6: acetonitrile / 8 h / 20 °C 7: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

	Multi-step reaction with 7 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 3: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 4: pyridine / 1 h / 20 °C 5: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 6: acetonitrile / 8 h / 20 °C 7: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 7 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 3: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 4: pyridine / 1 h / 20 °C 5: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 6: acetonitrile / 8 h / 20 °C 7: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 7 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 3: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 4: pyridine / 1 h / 20 °C 5: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 6: acetonitrile / 8 h / 20 °C 7: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 7 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 3: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 4: pyridine / 1 h / 20 °C 5: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 6: acetonitrile / 8 h / 20 °C 7: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 7 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 3: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 4: pyridine / 1 h / 20 °C 5: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 6: acetonitrile / 8 h / 20 °C 7: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 7 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 3: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 4: pyridine / 1 h / 20 °C 5: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 6: acetonitrile / 8 h / 20 °C 7: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 7 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 3: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 4: pyridine / 1 h / 20 °C 5: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 6: acetonitrile / 8 h / 20 °C 7: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[3]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[4]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[5]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[6]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[7]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[8]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[9]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[10]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

35
[ 58-96-8 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: pyridine / 1 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: acetonitrile / 8 h / 20 °C 4: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 4 steps 1: pyridine / 1 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: acetonitrile / 8 h / 20 °C 4: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

36
[ 69304-38-7 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: triethylamine / CH₂Cl₂ / 0.33 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 4: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 5: pyridine / 1 h / 20 °C 6: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 7: acetonitrile / 8 h / 20 °C 8: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 8 steps 1: triethylamine / CH₂Cl₂ / 0.33 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 4: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 5: pyridine / 1 h / 20 °C 6: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 7: acetonitrile / 8 h / 20 °C 8: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 8 steps 1: triethylamine / CH₂Cl₂ / 0.33 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 4: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 5: pyridine / 1 h / 20 °C 6: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 7: acetonitrile / 8 h / 20 °C 8: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

	Multi-step reaction with 8 steps 1: triethylamine / CH₂Cl₂ / 0.33 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 4: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 5: pyridine / 1 h / 20 °C 6: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 7: acetonitrile / 8 h / 20 °C 8: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 8 steps 1: triethylamine / CH₂Cl₂ / 0.33 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 4: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 5: pyridine / 1 h / 20 °C 6: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 7: acetonitrile / 8 h / 20 °C 8: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 8 steps 1: triethylamine / CH₂Cl₂ / 0.33 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 4: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 5: pyridine / 1 h / 20 °C 6: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 7: acetonitrile / 8 h / 20 °C 8: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 8 steps 1: triethylamine / CH₂Cl₂ / 0.33 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 4: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 5: pyridine / 1 h / 20 °C 6: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 7: acetonitrile / 8 h / 20 °C 8: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 8 steps 1: triethylamine / CH₂Cl₂ / 0.33 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 4: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 5: pyridine / 1 h / 20 °C 6: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 7: acetonitrile / 8 h / 20 °C 8: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 8 steps 1: triethylamine / CH₂Cl₂ / 0.33 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 4: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 5: pyridine / 1 h / 20 °C 6: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 7: acetonitrile / 8 h / 20 °C 8: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 8 steps 1: triethylamine / CH₂Cl₂ / 0.33 h / 20 °C 2: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 3: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / 20 °C 4: 4-nitrobenzaldoxime, N,N,N',N'-tetramethylguanidine / dioxane; H₂O / 0.05 h / 20 °C 5: pyridine / 1 h / 20 °C 6: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 7: acetonitrile / 8 h / 20 °C 8: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[3]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[4]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[5]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[6]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[7]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[8]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[9]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[10]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

37
[ 4105-38-8 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: acetonitrile / 8 h / 20 °C 3: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min
	Multi-step reaction with 3 steps 1: 1.) triethylamine, 2-mesitylenesulfonyl chloride, 4-N,N-dimethylaminopyridine, 2.) 1,4-diazabicyclo<2.2.2>octane, triethylamine / 1.) dichloromethane, 20 deg C, 1 h, 2.) dichloromethane, 20 deg C, 1 h 2: acetonitrile / 8 h / 20 °C 3: 1.) triethylamine, 2.) aq. ammonia / 1.) ethanol, 20 deg C, 10 min

Reference： [1]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]
[2]Zhou; Welch; Chattopadhyaya [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 10, p. 806 - 816]

38
[ 1748-04-5 ]
[ 10578-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: P₂S₅

Reference： [1]Fox et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 178,187]

39
[ 10578-79-7 ]
[ 71-91-0 ]
N₄-methyl-CTP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.94%		N4-Methyl-CTP: A solution of N4-Methyl-cytidine 46 (100.7 mg, 0.39 mmol; applied heat to make it soluble) and proton sponge (126.44 mg, 0.59 mmol, 1 .5 equiv.) in trimethyl phosphate (0.8 mL) was stirred for 10.0 minutes at 0 C. Phosphorus oxychloride (72.8 muIota_, 0.78 mmol, 2.0 equiv.) was added dropwise to the solution, and it was then kept stirring for 2.0 hours under N2 atmosphere. A mixture of tributylamine (378.85 muIota_, 1 .56 mmol, 4.0 equiv.) and bis(tributylammonium) pyrophosphate (642.0 mg, 1 .17 mmol, 3.0 equiv.) in acetonitrile (2.5 m L) was added at once. After -25 minutes, the reaction was quenched with 0.2 M TEAB buffer (17.0 mL) and the clear solution was stirred at room temperature for an hour. LCMS analysis indicated the formation of the corresponding triphosphate. The reaction mixture was then lyophilized overnight. The crude reaction mixture was HPLC purified (Shimadzu, Phenomenex C18 preparative column, 250 x 30.0 mm, 5.0 micron; gradient (1 %) : 100 % A for 3.0 min, then 1 % B/min, A = 100 mM TEAB buffer, B = ACN ; flow rate: 20.0 m L/min; retention time: 17.05-17.80 min). Fractions containing the desired were pooled and lyophilized to yield the N4- Methyl-CTP as a tetrakis(triethylammonium salt) (35.05 mg, 17.94 %, based on a270 = 1 1 ,000). UVmax = 270 nm ; MS: m/e 495.70 (M-H).

Reference： [1]Patent: WO2014/93924,2014,A1 .Location in patent: Page/Page column 257

40
[ 10578-79-7 ]
bis(tri-n-butylammonium) pyrophosphate [ No CAS ]
N₄-methyl-CTP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tributyl-amine; trichlorophosphate In acetonitrile	24 Example 24. A solution of N4-Methyl-cytidine 46 (100.7 mg, 0.39 mmol; applied heat to make it soluble) and proton sponge (126.44 mg, 0.59 mmol, 1.5 equiv.) in trimethyl phosphate (0.8 mL) was stirred for 10.0 minutes at 0 °C. Phosphorus oxychloride (72.8 μL, 0.78 mmol, 2.0 equiv.) was added dropwise to the solution, and it was then kept stirring for 2.0 hours under N2 atmosphere. A mixture of tributylamine (378.85 μL, 1.56 mmol, 4.0 equiv.) and bis(tributylammonium) pyrophosphate (642.0 mg, 1.17 mmol, 3.0 equiv.) in acetonitrile (2.5 mL) was added at once. After ∼25 minutes, the reaction was quenched with 0.2 M TEAB buffer (17.0 mL) and the clear solution was stirred at room temperature for an hour. LCMS analysis indicated the formation of the corresponding triphosphate. The reaction mixture was then lyophilized overnight. The crude reaction mixture was HPLC purified (Shimadzu, Phenomenex C18 preparative column, 250 x 30.0 mm, 5.0 micron; gradient (1 %): 100 % A for 3.0 min, then 1% B/min, A = 100 mM TEAB buffer, B = ACN; flow rate: 20.0 mL/min; retention time: 17.05-17.80 min). Fractions containing the desired were pooled and lyophilized to yield the N4-Methyl-CTP as a tetrakis(triethylammonium salt) (35.05 mg, 17.94 %, based on α270 = 11,000). UVmax = 270 nm; MS: m/e 495.70 (M-H).

Reference： [1]Current Patent Assignee: MODERNA THERAPEUTICS INC - EP2918275, 2015, A1

41
[ 10578-79-7 ]
[ 15715-58-9 ]
N₄-methyl-CTP tetrakistriethylammonium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.94%	Stage #1: 4-methylamino-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one With trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene at 0℃; for 0.166667h; Stage #2: With trichlorophosphate for 2h; Inert atmosphere; Stage #3: triethylamine carbonate Further stages;	24 Example 24. Synthesis of N4-methyl-CTP (00901014004) N4-Methyl-CTP: A solution of N4-Methyl-cytidine 46 (100.7 mg, 0.39 mmol; applied heat tomake it soluble) and proton sponge (126.44 mg, 0.59 mmol, 1.5 equiv.) in trimethyl phosphate (0.8mL) was stirred for 10.0 minutes at 0 00. Phosphorus oxychloride (72.8 pL, 0.78 mmol, 2.0 equiv.) was added dropwise to the solution, and it was then kept stirring for 2.0 hours under N2 atmosphere. A mixture of tributylamine (378.85 pL, 1 .56 mmol, 4.0 equiv.) and bis(tributylammonium) pyrophosphate (642.0 mg, 1.17 mmol, 3.0 equiv.) in acetonitrile (2.5 mL) was added at once. After25 minutes, the reaction was quenched with 0.2 M TEAB buffer (17.0 mL) and the clear solution was stirred at room temperature for an hour. LCMS analysis indicated the formation of the corresponding triphosphate. The reaction mixture was then lyophilized overnight. The crude reaction mixture was HPLC purified (Shimadzu, Phenomenex 018 preparative column, 250 x 30.0 mm, 5.0 micron; gradient (1 %): 100 % A for 3.0 mm, then 1% B/mm, A = 100 mM TEAB buffer, B = ACN; flow rate:20.0 mLlmin; retention time: 17.05-17.80 mm). Fractions containing the desired were pooled and lyophilized to yield the N4-Methyl-CTP as a tetrakis(triethylammonium salt) (35.05 mg, 17.94 %, based on a270 = 11,000). UVmax = 270 nm; MS: m/e 495.70 (M-H).

Reference： [1]Current Patent Assignee: MODERNA THERAPEUTICS INC - WO2015/196130, 2015, A2 Location in patent: Page/Page column 590

42
[ 10578-79-7 ]
[ 15715-58-9 ]
N₄-methyl-CTP tetrakis(triethylammonium) salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.94%	Stage #1: 4-methylamino-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene at 0℃; for 0.166667h; Stage #2: With trichlorophosphate for 2h; Inert atmosphere; Stage #3: triethylamine carbonate Further stages;	16; 24 Example 24. Synthesis of N4-methyl-CTP (00901014004) Example 24. Synthesis of N4-methyl-CTP (00901014004) N4-Methyl-CTP: A solution of N4-Methyl-cytidine 46 (1 00.7 mg, 0.39 mmol; applied heat to ke it soluble) and proton sponge (126.44 mg, 0.59 mmol, 1 .5 equiv.) in trimethyl phosphate (0.8 ) was stirred for 1 0.0 minutes at 0 °C. Phosphorus oxychloride (72.8 μΙ_, 0.78 mmol, 2.0 equiv.) s added dropwise to the solution, and it was then kept stirring for 2.0 hours under N2 atmosphere. mixture of tributylamine (378.85 μ Ι_, 1 .56 mmol, 4.0 equiv.) and bis(tributylammonium) ophosphate (642.0 mg, 1 .17 mmol, 3.0 equiv.) in acetonitrile (2.5 mL) was added at once. After 5 minutes, the reaction was quenched with 0.2 M TEAB buffer (17.0 mL) and the clear solution was red at room temperature for an hour. LCMS analysis indicated the formation of the corresponding hosphate. The reaction mixture was then lyophilized overnight. The crude reaction mixture was LC purified (Shimadzu, Phenomenex C18 preparative column, 250 x 30.0 mm, 5.0 micron; dient (1 %) : 100 % A for 3.0 min, then 1 % B/min, A = 1 00 mM TEAB buffer, B = ACN ; flow rate: 0 mL/min; retention time: 1 7.05-1 7.80 min). Fractions containing the desired were pooled and philized to yield the N4-Methyl-CTP as a tetrakis(triethylammonium salt) (35.05 mg, 1 7.94 %, sed on a270 = 1 1 ,000). UVmax = 270 nm; MS: m/e 495.70 (M-H).

Reference： [1]Current Patent Assignee: MODERNA THERAPEUTICS INC - WO2015/196128, 2015, A2 Location in patent: Page/Page column 598

43
[ 10578-79-7 ]
C₁₀H₁₄Cl₂N₃O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-methylamino-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one With trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene at 0℃; for 0.166667h; Stage #2: With trichlorophosphate for 2h; Inert atmosphere;	24 Example 24. Synthesis of N4-methyl-CTP (00901014004) Example 24. Synthesis of N4-methyl-CTP (00901014004) N4-Methyl-CTP: A solution of N4-Methyl-cytidine 46 (100.7 mg, 0.39 mmol; applied heat to make it soluble) and proton sponge (126.44 mg, 0.59 mmol, 1.5 equiv.) in trimethyl phosphate (0.8 mL) was stirred for 10.0 minutes at 0°C. Phosphorus oxychloride (72.8 µL, 0.78 mmol, 2.0 equiv.) was added dropwise to the solution, and it was then kept stirring for 2.0 hours under N2 atmosphere. A mixture of tributylamine (378.85 µL, 1.56 mmol, 4.0 equiv.) and bis(tributylammonium) pyrophosphate (642.0 mg, 1.17 mmol, 3.0 equiv.) in acetonitrile (2.5 mL) was added at once. After -25 minutes, the reaction was quenched with 0.2 M TEAB buffer (17.0 mL) and the clear solution was stirred at room temperature for an hour. LCMS analysis indicated the formation of the corresponding triphosphate. The reaction mixture was then lyophilized overnight. The crude reaction mixture was HPLC purified (Shimadzu, Phenomenex C18 preparative column, 250 x 30.0 mm, 5.0 micron; gradient (1 %): 100 % A for 3.0 min, then 1% B/min, A = 100 mM TEAB buffer, B = ACN; flow rate: 20.0 mL/min; retention time: 17.05-17.80 min). Fractions containing the desired were pooled and lyophilized to yield the N4-Methyl-CTP as a tetrakis(triethylammonium salt) (35.05 mg, 17.94 %, based on α270 = 11,000). UVmax = 270 nm; MS: m/e 495.70 (M-H).

Reference： [1]Current Patent Assignee: MODERNA THERAPEUTICS INC - EP2918275, 2015, A1 Location in patent: Paragraph 2073; 2074

44
[ 10578-79-7 ]
C₁₀H₁₆N₃O₁₃P₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 0.17 h / 0 °C 1.2: 2 h / Inert atmosphere 2.1: tributyl-amine; bis(tri-n-butylammonium) pyrophosphate / acetonitrile / 0.42 h

Reference： [1]Current Patent Assignee: MODERNA THERAPEUTICS INC - EP2918275, 2015, A1

45
[ 10578-79-7 ]
N₄-methyl-CTP tetrakis(triethylammonium) salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 0.17 h / 0 °C 1.2: 2 h / Inert atmosphere 2.1: tributyl-amine; bis(tri-n-butylammonium) pyrophosphate / acetonitrile / 0.42 h 3.1: aq. buffer / 1 h / 20 °C

Reference： [1]Current Patent Assignee: MODERNA THERAPEUTICS INC - EP2918275, 2015, A1

46
[ 10578-79-7 ]
[ 65-46-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With manganese(IV) oxide; C₁₇H₂₀N₄O₉P^(1-)*Na⁽¹⁺⁾; oxygen In water; acetonitrile at 20℃; for 7h; Irradiation; chemoselective reaction;

Reference： [1]Xie, Li-Jun; Yang, Xiao-Ti; Wang, Rui-Li; Cheng, Hou-Ping; Li, Zhi-Yan; Liu, Li; Mao, Lanqun; Wang, Ming; Cheng, Liang [Angewandte Chemie - International Edition, 2019, vol. 58, # 15, p. 5028 - 5032][Angew. Chem., 2019, vol. 131, # 15, p. 5082 - 5086,5]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	10578-79-7	MDL No. :	MFCD23701766
Formula :	C₁₀H₁₅N₃O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LZCNWAXLJWBRJE-ZOQUXTDFSA-N
M.W :	257.24	Pubchem ID :	101436
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
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Prevention
Code	Phrase
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P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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P231	Handle under inert gas.
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
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Response
Code	Phrase
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
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P342	If experiencing respiratory symptoms:
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
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P413
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P402 + P404	Store in a dry place. Store in a closed container.
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Disposal
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P501	Dispose of contents/container to ...
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 10578-79-7 ] {[proInfo.proName]}

Quality Control of [ 10578-79-7 ]

Related Doc. of [ 10578-79-7 ]

Product Details of [ 10578-79-7 ]

Safety of [ 10578-79-7 ]

Application In Synthesis of [ 10578-79-7 ]

[ 10578-79-7 ] Synthesis Path-Upstream 1~1

[ 10578-79-7 ] Synthesis Path-Downstream 1~46

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry