* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference:
[1] Journal of Organic Chemistry, 1992, vol. 57, # 12, p. 3473 - 3478
2
[ 108-24-7 ]
[ 65-46-3 ]
[ 3768-18-1 ]
Yield
Reaction Conditions
Operation in experiment
96%
for 3 h; Reflux
In a 500 mL three-necked flask was added 50.0 g of Compound 3 powder and 250 mL of acetonitrile and 25 mL of acetic anhydride, stirred and refluxed for 3 h, cooled to room temperature and filtered with suction. The solid was washed with acetonitrile twice and the filter cake was dried to give 56.3 g of compound 4 with a yield of 96.0 percent.
95%
for 0.0111111 h; Microwave radiation
To a solution of cytidine (1.22 g, 5.00 mmol) in DMF(40 mL) is added acetic anhydride (0.94 mL, 10.00 mmol). The solution is treated with microwave radiation (Panasonic, 1000 Watts) at full power for 40 seconds. The solution is concentrated in vacuo and the residue is co-evaporated with methanol (2.x.20 mL) to give 4-N-acetyl-cytidine (1.43 g, 95.0percent) as a white powder. MS (FAB):m/z 286 (MH+).
87%
for 24 h;
Cytidine (100.Og, 0.41 mol) was dissolved in DMF (500 ml), acetic anhydride (42.5 ml, 45.9 g, 0.45 mol) was added and the whole was left for 24 h. Solvent was evaporated, the residue boiled with methanol (40 ml) and cooled. Crystals were filtered and dried to furnish Λ^-acetylcytidine (102 g, 87.0percent).
Reference:
[1] Tetrahedron Letters, 1997, vol. 38, # 41, p. 7253 - 7254
[2] Patent: CN107033205, 2017, A, . Location in patent: Paragraph 0033; 0034; 0035; 0036
[3] Patent: US6822089, 2004, B1, . Location in patent: Page column 13
[4] Nucleosides and Nucleotides, 1997, vol. 16, # 4, p. 469 - 474
[5] Patent: WO2010/108140, 2010, A1, . Location in patent: Page/Page column 138
[6] Journal of Organic Chemistry, 2002, vol. 67, # 26, p. 9331 - 9339
[7] Journal of the American Chemical Society, 1983, vol. 105, # 12, p. 4059 - 4065
[8] Phosphorus, Sulfur and Silicon and Related Elements, 2002, vol. 177, # 6-7, p. 1783 - 1786
[9] Tetrahedron Letters, 1998, vol. 39, # 14, p. 1897 - 1900
3
[ 65-46-3 ]
[ 3768-18-1 ]
Reference:
[1] Tetrahedron Letters, 1991, vol. 32, # 24, p. 2817 - 2820
[2] Bioscience, Biotechnology and Biochemistry, 2000, vol. 64, # 2, p. 363 - 368
[3] Tetrahedron Letters, 1989, vol. 30, # 1, p. 71 - 74
[4] Patent: US5808039, 1998, A,
4
[ 5040-18-6 ]
[ 3768-18-1 ]
Reference:
[1] Bioscience, Biotechnology and Biochemistry, 2000, vol. 64, # 2, p. 363 - 368
5
[ 64-19-7 ]
[ 65-46-3 ]
[ 3768-18-1 ]
Reference:
[1] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 7, p. 2061 - 2064
(S)-Methoxy-phenyl-acetic acid (R)-[(3aS,6R,6aR)-6-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-(diethoxy-phosphoryl)-methyl ester[ No CAS ]
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester[ No CAS ]
(R)-Methoxy-phenyl-acetic acid (1S,2S)-2-[(3aR,4R,6R,6aR)-6-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1-(diethoxy-phosphoryl)-2-hydroxy-ethyl ester[ No CAS ]
(S)-Methoxy-phenyl-acetic acid (1S,2S)-2-[(3aR,4R,6R,6aR)-6-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1-(diethoxy-phosphoryl)-2-hydroxy-ethyl ester[ No CAS ]
(S)-Methoxy-phenyl-acetic acid (1S,2S)-1-[(3aR,4S,6R,6aR)-6-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-(diethoxy-phosphoryl)-2-((S)-2-methoxy-2-phenyl-acetoxy)-ethyl ester[ No CAS ]
Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl ester allyl ester[ No CAS ]
Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methylsulfanylmethoxy-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester[ No CAS ]
I-(2,5-Di-O-acetyl-3-bromo-3-deoxy-β-D-xylofuranosyl)-N4-acetylcytosine[ No CAS ]
[ 52482-84-5 ]
Yield
Reaction Conditions
Operation in experiment
In dichloromethane; acetonitrile;
Example 1 1-(2,5-Di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)-N4-acetylcytosine (2, R=H). To a suspension of <strong>[3768-18-1]N4-acetylcytidine</strong> (5.7 g, 0.02 mol) in acetonitrile (300 mL) is added acetyl bromide (15 mL, 0.2 mol) over 30 minutes under reflux. The mixture is refluxed for 4 hours, and then concentrated in vacuo to dryness. The residue is dissolved in methylene chloride (150 mL) and washed with water (150 mL). The organic layer is dried (Na2SO4), evaporated, and the residue crystallized from ethanol to give I-(2,5-Di-O-acetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)-N4-acetylcytosine (2, R=H, 3.4 g, 40percent), mp 179-180° C. 1H NMR (CDCl3) delta: 10.2 (bs, 1H, NHAC), 8.1 (d, 1H, H-6, 35,6=7.5 Hz), 7.5 (d, 1H, H-5, J5,6=7.5 Hz), 6.0 (d, 1H, H-1', J1',2'<1 Hz), 5.5 (d, 1H, H-2', J1',2'<1, J2',3'=0 Hz), 4.2-4.7 (m, 4H, H-3',4',5',5"), 2.0-2.4 (3s, 9H, 3Ac).
1,6-di-O-acetyl-4-azido-2,3-di-O-benzyl-4-deoxy-α,β-D-glucopyranose[ No CAS ]
[ 3768-18-1 ]
C26H28N6O7[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
To a 1 litre round bottom flask under argon is added a nitrogenous base in dichloroethane or acetonitrile. Bis(trimethylsilyl)-acetamide (BSA, 15 mL) is added dropwise to the suspension and heated at 60° C. until a clear solution is formed. A second solution of azido sugar (6, 14.7 g) in dichloroethane (100 mL) or acetonitrile (100 mL) is treated with a lewis acid for 20 min. and then the silylated nitrogenous base is added. The mixture is heated for 2 days at 65° C. and then evaportaed under reduced pressure. The resultant solid is purified on silica gel, eluting with 10percent methanol in dichloromethane. [0196] Example 1. N-Acetyl cytidine (7.8 g) is reacted in dichloroethane (500 mL) with tin(IV)chloride (13 mL), according to the general procedure to give compound 7a.
To a solution of Lambda^-acetylcytidine (65.0 g, 0.228 mol) in anhydrous pyridine (60OmL) cooled in an ice bath, DMTrCl (84.7 g, 0.251 mol) was added. The reaction mixture was stirred at room temperature overnight. To the reaction mixture cooled with an ice bath, THF (600 ml) and AgNO3 (58.1 g, 0.342 mmol) were added. Then TBSCl (51.5 g, 0.342 mmol) was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered, solvent was removed under vacuum to give a residue which was diluted with EtOAc (500 mL) and washed with water (200 ml) and brine (200 ml). The organic layer was separated and dried over anhydrous Na2SO4 and the filtrate was concentrated to a syrup which was purified by chromatography on silica gel (eluted with PE : EA = 5:1 to 3 : 1) to give N4-acetyl-2'-O-(t-butyldimethylsilyl)-5'-O- (4,4'-dimethoxytrityl)cytidine as yellow solid (80 g, 50percent). 1H NMR (CDCl3) delta 8.39 (d, J = 7.6 Hz, IH), 7.34 (dd, Jl = 1.6 Hz, J2 = 8.4 Hz, 2H), 7.21 - 7.27 (m, 6H), 7.02 (d, J = 7.2 Hz, IH), 6.80 (dd, Jl = 2.0 Hz, J2 = 6.8 Hz, 4H), 5.82 (d, J = 1.2 Hz, IH), 4.26 - 4.32 (m, IH), 4.20 (dd, Jl = 1.2 Hz, J2 = 4.4 Hz, IH), 4.00 - 4.02 (m, IH), 3.74 (d, J = 1.6 Hz, 6 H), 3.43 - 3.53 (m, 2H), 2.32 (d, J = 9.6 Hz, IH), 2.18 (s, 3H), 0.86 (s, 9H), 0.22 (s, 3H), 0.11 (s, 3H).