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Chemistry
Heterocyclic Building Blocks
Pyrimidines
4′-Thiouridine
Chemistry
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Heterocyclic Building Blocks
Organic Building Blocks Asymmetric Synthesis Cell Cycle
Pyrimidines
Amides Alcohols Chiral Building Blocks Nucleoside Antimetabolite/Analog

[ CAS No. 6741-73-7 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 6741-73-7
Chemical Structure| 6741-73-7
Structure of 6741-73-7 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 6741-73-7 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 6741-73-7 ]

CAS No. :6741-73-7 MDL No. :MFCD22666335
Formula : C9H12N2O5S Boiling Point : -
Linear Structure Formula :- InChI Key :MUSPKJVFRAYWAR-XVFCMESISA-N
M.W : 260.27 Pubchem ID :11219149
Synonyms :
1-(4-Thio-beta-D-ribofuranosyl)uracil

Safety of [ 6741-73-7 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6741-73-7 ]

* 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.

  • Downstream synthetic route of [ 6741-73-7 ]

[ 6741-73-7 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 69304-37-6 ]
  • [ 6741-73-7 ]
  • [ 166249-03-2 ]
YieldReaction ConditionsOperation in experiment
80% In pyridine at 0℃; for 2 - 4h; 28.a Compound 13 (1.1 g, 4.23 mmole) was dissolved in anhydrous pyridine (10 mL) under a nitrogen atmosphere and cooled in an ice bath. TIPDSC12 (1.4 mL, 4.44 mmole) was added drop-wise with vigorous stirring. Stirring was continued at the same temperature for an additional 2 to 4 h. When all of 13 had been consumed the reaction was quenched by pouring onto ice. The mixture was separated between ethyl acetate and water and the ethyl acetate layer was washed thrice with cold sat. sodium bicarbonate solution and once with brine. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material was purified by flash chromatography (5% methanol in dichloromethane) to give Compound 35 (1.7 g, 80% yield).
61% With pyridine Ambient temperature;
Reference： [1]Current Patent Assignee: IONIS PHARMACEUTICALS - WO2005/27962, 2005, A1 Location in patent: Page/Page column 81-82
[2]Jeong; Nicklaus; George; Marquez [Tetrahedron Letters, 1994, vol. 35, # 41, p. 7573 - 7576]
  • 2
  • 2’,3’,5’-tri-O-benzoyl,1’-β-(4’-thio-D-ribofuranosyl)uracil [ No CAS ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
96% With methanol; ammonia at 0 - 40℃; for 72h;
38% With sodium hydroxide In ethanol
Reference： [1]Guinan, Mieke; Hawes, Chris S.; Huang, Ningwu; Lima, Marcelo A.; Miller, Gavin J.; Smith, Mark [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1401 - 1406]
[2]Leydier; Bellon; Barascut; Imbach [Nucleosides and Nucleotides, 1995, vol. 14, # 3-5, p. 1027 - 1030]
  • 3
  • [ 40615-36-9 ]
  • [ 6741-73-7 ]
  • [ 149359-04-6 ]
YieldReaction ConditionsOperation in experiment
80% In pyridine at 20℃; 14 Compound 13 (2 g, 7.754 mmol) was dissolved in dry pyridine (20 mL), 4, 4'-dimethoxytrityl chloride (2.9 g, 8.53 mmol) was added and the mixture stirred at room temperature overnight. The reaction was quenched with methanol and taken up in ethyl acetate (200 ML). The ethyl acetate solution was washed twice with saturated sodium bicarbonate solution, once with water, once with brine, and dried over anhydrous sodium sulfate. The solvents were removed under reduced pressure and the residue purified by flash chromatography (7% methanol in dichloromethane). The desired fractions were pooled and concentrated to give Compound 14 (3.0 g) in 80% yield. The structure of Compound 14 was confirmed by'H NMR & ESMS
With pyridine
Reference： [1]Current Patent Assignee: IONIS PHARMACEUTICALS - WO2005/27962, 2005, A1 Location in patent: Page/Page column 74-75
[2]Leydier; Bellon; Barascut; Imbach [Nucleosides and Nucleotides, 1995, vol. 14, # 3-5, p. 1027 - 1030]
  • 4
  • [ 58479-61-1 ]
  • [ 6741-73-7 ]
  • 5'-O-tert-butyldiphenylsilyl-4-thiouridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With dmap In pyridine at 20℃; for 12h; 51.i 4-TLIIO-URIDINE (2.95 g, 11.43 mmol) was mixed with DMAP (0.02 g, 0.15 mmol) and dried under reduced pressure over PZ05. THE reaction mixture was dissolved in anhydrous pyridine (15 mL) and tert.- butyldiphenylsilyl chloride (3.27 mL, 13 mmol) was added. Stirred the reaction mixture at room temperature under argon atmosphere for 12 h. The solvent was removed under reduced pressure residue dissolved in ethyl acetate (100 ML). The organic phase washed with aqueous NAHCO3 (5%, 50 ML), brine (50 ML). Orgnic layer separated and dried over anhydrous NA2SO4 and concentrated under reduced pressure. The residue obtained was purified by flash silica gel column chromatography and eluted with dichloromethane containing in cremental amount ODF METHANOL (5-10%) to yield Compound 112 (5.21 g, 91 %) as a foam.'HNMR (200 MHz, DMSO-d6) : 11.33 (s, 1H), 7.84 (d, J = 8.2 Hz, 1H,), 7. 66- 7. 33 (M, 10H), 5.86 (d, J = 6.4 Hz, 1H), 5.58 (d, J = 5.6 Hz, 1H), 5.47 (d, J = 8.2 Hz, 1 H), 5.34 (d, J = 4.4 Hz, 1H), 4.09 (m, 2H), 3.97 (m, 1H), 3.77 (M, 1H), 3.35 (M, 1H), 1.01 (s, 9H); MS (API-ES) 71L/Z 499.1 [M + H] +.
Reference： [1]Current Patent Assignee: IONIS PHARMACEUTICALS - WO2005/27962, 2005, A1 Location in patent: Page/Page column 96-97
  • 5
  • 2,4-Dimethoxy-benzoic acid (2R,3R,4S,5R)-4-hydroxy-5-hydroxymethyl-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-thiophen-3-yl ester [ No CAS ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
With ammonia In methanol at 20℃; for 24h;
Reference： [1]Naka, Takashi; Minakawa, Noriaki; Abe, Hiroshi; Kaga, Daisuke; Matsuda, Akira [Journal of the American Chemical Society, 2000, vol. 122, # 30, p. 7233 - 7243]
  • 6
  • [ 994-30-9 ]
  • [ 6741-73-7 ]
  • 1-[2,3,5-tris-O-(triethylsilyl)-4-thio-β-D-ribofuranosyl]uracil [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 11h;
42.7 mg With 1H-imidazole In N,N-dimethyl-formamide at 0℃;
Reference： [1]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
[2]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 7
  • [ 457653-25-7 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,2'-anhydro-[1-((2S)-2-deoxy-4-thio-β-D-ribofuranosyl)uracil] With lithium benzoate; benzoic acid In N,N-dimethyl-formamide at 140℃; Stage #2: With sodium methylate In methanol at 20℃; for 5h; Further stages.;
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 8
  • [ 1053628-67-3 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
90 mg With ammonia In methanol at 20℃; for 24h;
Reference： [1]Nishizono, Naozumi; Baba, Ryosuke; Nakamura, Chika; Oda, Kazuaki; Machida, Minoru [Organic and biomolecular chemistry, 2003, vol. 1, # 21, p. 3692 - 3697]
  • 9
  • [ 291758-11-7 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 98 percent / pyridine / 12 h / 20 °C 2.1: Et3N; TMSOTf / CH2Cl2 / 1 h / 20 °C 2.2: TMSOTf; iodosobenzene / CH2Cl2 / 0.08 h / 0 °C 2.3: 53 percent / Et3N / CH2Cl2 / 12 h / 0 °C 3.1: NH4F / methanol / 12 h / Heating 4.1: 90 mg / NH3 / methanol / 24 h / 20 °C
Multi-step reaction with 4 steps 1.1: 98 percent / pyridine / 12 h / 20 °C 2.1: Et3N; TMSOTf / CH2Cl2 / 1 h / 20 °C 2.2: PhI(OCOCF3)2; Et3N / CH2Cl2 / 12 h / 0 °C 3.1: NH4F / methanol / 12 h / Heating 4.1: 90 mg / NH3 / methanol / 24 h / 20 °C
Reference： [1]Nishizono, Naozumi; Baba, Ryosuke; Nakamura, Chika; Oda, Kazuaki; Machida, Minoru [Organic and biomolecular chemistry, 2003, vol. 1, # 21, p. 3692 - 3697]
[2]Nishizono, Naozumi; Baba, Ryosuke; Nakamura, Chika; Oda, Kazuaki; Machida, Minoru [Organic and biomolecular chemistry, 2003, vol. 1, # 21, p. 3692 - 3697]
  • 10
  • [ 658052-48-3 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Et3N; TMSOTf / CH2Cl2 / 1 h / 20 °C 1.2: TMSOTf; iodosobenzene / CH2Cl2 / 0.08 h / 0 °C 1.3: 53 percent / Et3N / CH2Cl2 / 12 h / 0 °C 2.1: NH4F / methanol / 12 h / Heating 3.1: 90 mg / NH3 / methanol / 24 h / 20 °C
Multi-step reaction with 3 steps 1.1: Et3N; TMSOTf / CH2Cl2 / 1 h / 20 °C 1.2: PhI(OCOCF3)2; Et3N / CH2Cl2 / 12 h / 0 °C 2.1: NH4F / methanol / 12 h / Heating 3.1: 90 mg / NH3 / methanol / 24 h / 20 °C
Reference： [1]Nishizono, Naozumi; Baba, Ryosuke; Nakamura, Chika; Oda, Kazuaki; Machida, Minoru [Organic and biomolecular chemistry, 2003, vol. 1, # 21, p. 3692 - 3697]
[2]Nishizono, Naozumi; Baba, Ryosuke; Nakamura, Chika; Oda, Kazuaki; Machida, Minoru [Organic and biomolecular chemistry, 2003, vol. 1, # 21, p. 3692 - 3697]
  • 11
  • [ 658052-50-7 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NH4F / methanol / 12 h / Heating 2: 90 mg / NH3 / methanol / 24 h / 20 °C
Reference： [1]Nishizono, Naozumi; Baba, Ryosuke; Nakamura, Chika; Oda, Kazuaki; Machida, Minoru [Organic and biomolecular chemistry, 2003, vol. 1, # 21, p. 3692 - 3697]
  • 12
  • [ 134938-97-9 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: boron tribromide; methanol; pyridine / CH2Cl2 / 0.5 h / -70 °C 2.1: 625 mg / imidazole / dimethylformamide / 20 °C 3.1: m-chloroperoxybenzoic acid / CH2Cl2 / 1.5 h / -70 °C 3.2: 57 percent / diisopropylethylamine / xylene / Heating 4.1: 88 percent / N-iodosuccinimide / acetonitrile / 0 °C 5.1: 95 percent / 1,5-diazabicyclo[4.3.0]non-5-ene / acetonitrile / 0 °C 6.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 7.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 7.2: sodium methoxide / methanol / 5 h / 20 °C
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 13
  • [ 134700-25-7 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: 5.46 g / imidazole; DMF / 20 °C 2.1: acetic acid / 2 h / 20 °C 3.1: 670 mg / ammonia / methanol / 20 °C 4.1: 4-dimethylaminopyridine / CH2Cl2 / 0 °C 5.1: 113 mg / CH2Cl2 / 20 °C 6.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 7.1: 30.9 mg / 4-(dimethylamino)pyridine; DMF / 0 °C 8.1: 88 percent / N-iodosuccinimide / acetonitrile / 0 °C 9.1: 95 percent / 1,5-diazabicyclo[4.3.0]non-5-ene / acetonitrile / 0 °C 10.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 11.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 11.2: sodium methoxide / methanol / 5 h / 20 °C
Multi-step reaction with 6 steps 1.1: 625 mg / imidazole / dimethylformamide / 20 °C 2.1: m-chloroperoxybenzoic acid / CH2Cl2 / 1.5 h / -70 °C 2.2: 57 percent / diisopropylethylamine / xylene / Heating 3.1: 88 percent / N-iodosuccinimide / acetonitrile / 0 °C 4.1: 95 percent / 1,5-diazabicyclo[4.3.0]non-5-ene / acetonitrile / 0 °C 5.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 6.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 6.2: sodium methoxide / methanol / 5 h / 20 °C
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
[2]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 14
  • (2R,3S)-2-Hydroxymethyl-2,3-dihydro-thiophen-3-ol [ No CAS ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 30.9 mg / 4-(dimethylamino)pyridine; DMF / 0 °C 2.1: 88 percent / N-iodosuccinimide / acetonitrile / 0 °C 3.1: 95 percent / 1,5-diazabicyclo[4.3.0]non-5-ene / acetonitrile / 0 °C 4.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 5.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 5.2: sodium methoxide / methanol / 5 h / 20 °C
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 15
  • [ 209048-62-4 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 88 percent / N-iodosuccinimide / acetonitrile / 0 °C 2.1: 95 percent / 1,5-diazabicyclo[4.3.0]non-5-ene / acetonitrile / 0 °C 3.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 4.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 4.2: sodium methoxide / methanol / 5 h / 20 °C
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 16
  • 3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-1,4-dithio-D-erythro-pentofuranose [ No CAS ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: 4-dimethylaminopyridine / CH2Cl2 / 0 °C 2.1: 113 mg / CH2Cl2 / 20 °C 3.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 4.1: 30.9 mg / 4-(dimethylamino)pyridine; DMF / 0 °C 5.1: 88 percent / N-iodosuccinimide / acetonitrile / 0 °C 6.1: 95 percent / 1,5-diazabicyclo[4.3.0]non-5-ene / acetonitrile / 0 °C 7.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 8.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 8.2: sodium methoxide / methanol / 5 h / 20 °C
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 17
  • [ 209048-59-9 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 2.1: 30.9 mg / 4-(dimethylamino)pyridine; DMF / 0 °C 3.1: 88 percent / N-iodosuccinimide / acetonitrile / 0 °C 4.1: 95 percent / 1,5-diazabicyclo[4.3.0]non-5-ene / acetonitrile / 0 °C 5.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 6.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 6.2: sodium methoxide / methanol / 5 h / 20 °C
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 18
  • Acetic acid (4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl ester [ No CAS ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: 670 mg / ammonia / methanol / 20 °C 2.1: 4-dimethylaminopyridine / CH2Cl2 / 0 °C 3.1: 113 mg / CH2Cl2 / 20 °C 4.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 5.1: 30.9 mg / 4-(dimethylamino)pyridine; DMF / 0 °C 6.1: 88 percent / N-iodosuccinimide / acetonitrile / 0 °C 7.1: 95 percent / 1,5-diazabicyclo[4.3.0]non-5-ene / acetonitrile / 0 °C 8.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 9.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 9.2: sodium methoxide / methanol / 5 h / 20 °C
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 19
  • [ 209048-57-7 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: acetic acid / 2 h / 20 °C 2.1: 670 mg / ammonia / methanol / 20 °C 3.1: 4-dimethylaminopyridine / CH2Cl2 / 0 °C 4.1: 113 mg / CH2Cl2 / 20 °C 5.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 6.1: 30.9 mg / 4-(dimethylamino)pyridine; DMF / 0 °C 7.1: 88 percent / N-iodosuccinimide / acetonitrile / 0 °C 8.1: 95 percent / 1,5-diazabicyclo[4.3.0]non-5-ene / acetonitrile / 0 °C 9.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 10.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 10.2: sodium methoxide / methanol / 5 h / 20 °C
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 20
  • [ 209048-67-9 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 95 percent / 1,5-diazabicyclo[4.3.0]non-5-ene / acetonitrile / 0 °C 2.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 3.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 3.2: sodium methoxide / methanol / 5 h / 20 °C
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 21
  • [ 457653-07-5 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: m-chloroperoxybenzoic acid / CH2Cl2 / 1.5 h / -70 °C 1.2: 57 percent / diisopropylethylamine / xylene / Heating 2.1: 88 percent / N-iodosuccinimide / acetonitrile / 0 °C 3.1: 95 percent / 1,5-diazabicyclo[4.3.0]non-5-ene / acetonitrile / 0 °C 4.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 5.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 5.2: sodium methoxide / methanol / 5 h / 20 °C
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 22
  • [ 457653-24-6 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 2.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 2.2: sodium methoxide / methanol / 5 h / 20 °C
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 23
  • methanesulfonic acid 4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-5-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl ester [ No CAS ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 113 mg / CH2Cl2 / 20 °C 2.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 3.1: 30.9 mg / 4-(dimethylamino)pyridine; DMF / 0 °C 4.1: 88 percent / N-iodosuccinimide / acetonitrile / 0 °C 5.1: 95 percent / 1,5-diazabicyclo[4.3.0]non-5-ene / acetonitrile / 0 °C 6.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C 7.1: lithium benzoate; benzoic acid / dimethylformamide / 140 °C 7.2: sodium methoxide / methanol / 5 h / 20 °C
Reference： [1]Haraguchi, Kazuhiro; Takahashi, Haruhiko; Shiina, Noriaki; Horii, Chikafumi; Yoshimura, Yuichi; Nishikawa, Ayako; Sasakura, Eiko; Nakamura, Kazuo T.; Tanaka, Hiromichi [Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 5919 - 5927]
  • 24
  • [ 869347-03-5 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 41 percent / 6 h / 110 °C 2: N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile 3: ammonium fluoride / methanol / 12 h / Heating 4: NH3 / methanol / 24 h / 20 °C
Multi-step reaction with 3 steps 1: 80 percent / TMSOTf; Et3N / CH2Cl2; toluene / 0.08 h / 20 °C 2: ammonium fluoride / methanol / 12 h / Heating 3: NH3 / methanol / 24 h / 20 °C
Reference： [1]Naka, Takashi; Minakawa, Noriaki; Abe, Hiroshi; Kaga, Daisuke; Matsuda, Akira [Journal of the American Chemical Society, 2000, vol. 122, # 30, p. 7233 - 7243]
[2]Naka, Takashi; Minakawa, Noriaki; Abe, Hiroshi; Kaga, Daisuke; Matsuda, Akira [Journal of the American Chemical Society, 2000, vol. 122, # 30, p. 7233 - 7243]
  • 25
  • [ 291758-26-4 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile 2: ammonium fluoride / methanol / 12 h / Heating 3: NH3 / methanol / 24 h / 20 °C
Reference： [1]Naka, Takashi; Minakawa, Noriaki; Abe, Hiroshi; Kaga, Daisuke; Matsuda, Akira [Journal of the American Chemical Society, 2000, vol. 122, # 30, p. 7233 - 7243]
  • 26
  • [ 291758-14-0 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonium fluoride / methanol / 12 h / Heating 2: NH3 / methanol / 24 h / 20 °C
Reference： [1]Naka, Takashi; Minakawa, Noriaki; Abe, Hiroshi; Kaga, Daisuke; Matsuda, Akira [Journal of the American Chemical Society, 2000, vol. 122, # 30, p. 7233 - 7243]
  • 27
  • [ 6741-73-7 ]
  • [ 166249-07-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 61 percent / pyridine / Ambient temperature 2: DMAP / Ambient temperature 3: Bu3SnH, Et3B 4: 78 percent / Et3N / tetrahydrofuran / 80 °C 5: 63 percent / n-Bu4F / tetrahydrofuran / Ambient temperature
Reference： [1]Jeong; Nicklaus; George; Marquez [Tetrahedron Letters, 1994, vol. 35, # 41, p. 7573 - 7576]
  • 28
  • [ 6741-73-7 ]
  • (2R,3S,3aS,9aR)-3-Hydroxy-2-trityloxymethyl-2,3,3a,9a-tetrahydro-thieno[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 60 percent 2: 80 percent / 1,1'-thiocarbonyldiimidazole / toluene / Heating
Reference： [1]Jeong, Lak S.; Nicklaus, Marc C.; George, Cliff; Marquez, Victor E. [Tetrahedron Letters, 1994, vol. 35, # 41, p. 7569 - 7572]
  • 29
  • [ 6741-73-7 ]
  • [ 166249-06-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 61 percent / pyridine / Ambient temperature 2: DMAP / Ambient temperature 3: Bu3SnH, Et3B 4: 78 percent / Et3N / tetrahydrofuran / 80 °C
Reference： [1]Jeong; Nicklaus; George; Marquez [Tetrahedron Letters, 1994, vol. 35, # 41, p. 7573 - 7576]
  • 30
  • [ 6741-73-7 ]
  • [ 166249-11-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 61 percent / pyridine / Ambient temperature 2: DMAP / Ambient temperature 3: Bu3SnH, Et3B 4: 78 percent / Et3N / tetrahydrofuran / 80 °C 5: 63 percent / n-Bu4F / tetrahydrofuran / Ambient temperature 6: 79 percent / pyridine / 100 °C 7: 1.) DAST; 2.) KF / 1.) CH2Cl2, -78 deg C, 15 min.; 2.) CH2Cl2, rt., 5h
Reference： [1]Jeong; Nicklaus; George; Marquez [Tetrahedron Letters, 1994, vol. 35, # 41, p. 7573 - 7576]
  • 31
  • [ 6741-73-7 ]
  • [ 166249-10-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 61 percent / pyridine / Ambient temperature 2: DMAP / Ambient temperature 3: Bu3SnH, Et3B 4: 78 percent / Et3N / tetrahydrofuran / 80 °C 5: 63 percent / n-Bu4F / tetrahydrofuran / Ambient temperature 6: 79 percent / pyridine / 100 °C
Reference： [1]Jeong; Nicklaus; George; Marquez [Tetrahedron Letters, 1994, vol. 35, # 41, p. 7573 - 7576]
  • 32
  • [ 6741-73-7 ]
  • [ 166249-14-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 61 percent / pyridine / Ambient temperature 2: DMAP / Ambient temperature 3: Bu3SnH, Et3B 4: 78 percent / Et3N / tetrahydrofuran / 80 °C 5: 63 percent / n-Bu4F / tetrahydrofuran / Ambient temperature 6: 79 percent / pyridine / 100 °C 7: 1.) DAST; 2.) KF / 1.) CH2Cl2, -78 deg C, 15 min.; 2.) CH2Cl2, rt., 5h 8: 1.) BF3*Et2O/LiBr; / 1.) acetic anhydride, rt. 48 h
Reference： [1]Jeong; Nicklaus; George; Marquez [Tetrahedron Letters, 1994, vol. 35, # 41, p. 7573 - 7576]
  • 33
  • [ 291758-14-0 ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-d-ribofuranosyl] uracil With triethylamine tris(hydrogen fluoride); triethylamine In tetrahydrofuran at 20℃; for 4 - 5h; Stage #2: With ammonia In methanol at 20℃; 13 Compound 12 (1.2 G, 1.90 mmole) was dissolved in dry THF under nitrogen. TEA (1.3 mL, 9.5 mmole, 5 eq. ) and TREAT. HF (2.8 mL, 20 mmole, 10 eq. ) were added and the mixture stirred at room temperature for 4 to 5 h. The solvent was removed under reduced pressure and the residue was co- evaporated three times with toluene. Methanolic ammonia (20 mL) was added and the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (10% methanol in dichloromethane) to give Compound 13 (420 MG) in 90% yield. Compound 13 was also synthesized using literature procedure (Naka et al. in J. Am. Chem. Soc. , Vol. 122, No. 30,2000) with few modifications that resulted in significant increase in yields.
Reference： [1]Current Patent Assignee: IONIS PHARMACEUTICALS - WO2005/27962, 2005, A1 Location in patent: Page/Page column 74
  • 34
  • [ 6741-73-7 ]
  • [ 457653-25-7 ]
YieldReaction ConditionsOperation in experiment
98% With bis(phenyl) carbonate; Sodium hydrogenocarbonate In N,N-dimethyl-formamide at 100℃; for 18h;
76% With bis(phenyl) carbonate; Sodium hydrogenocarbonate In N,N-dimethyl acetamide at 100℃; for 2h; 48.a 4'-Thio-uridine (13) (1 gm, 3.8 mmole), sodium bicarbonate (5 mg), diphenyl carbonate (900 mg, 4.0 mmol) were dissolved in 10 mL dry N, N-DIMETHYLACETAMIDE and heated at 100 °C for 2 hrs. The reaction mixture was cooled to room temperature and poured into rapidly stirring ether. The resulting precipitate was isolated by centrifugation (800 mg, 76% yield) and used as such in the next step. 1H NMR (DMSO-d6): 8 7.8 (d, 1H), 6.2 (d, 1H), 5.82 (M, 2H), 5.4 (d, 1H), 5 : 2 (M, 1H), 4.6 (M, 1H), 3.2-3. 4 (M, 3H). ESMS=243 (MH), calc for CGHION204S = 242.03.
With bis(phenyl) carbonate; Sodium hydrogenocarbonate In N,N-dimethyl acetamide at 100℃; 41.A Compound 13 is heated with diphenylcarbonate and sodium bicarbonate at 100 °C in dimethylacetamide to yield Compound 50.
Reference： [1]Guinan, Mieke; Hawes, Chris S.; Huang, Ningwu; Lima, Marcelo A.; Miller, Gavin J.; Smith, Mark [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1401 - 1406]
[2]Current Patent Assignee: IONIS PHARMACEUTICALS - WO2005/27962, 2005, A1 Location in patent: Page/Page column 91
[3]Current Patent Assignee: IONIS PHARMACEUTICALS - WO2005/27962, 2005, A1 Location in patent: Page/Page column 86
  • 35
  • isopropyl (2R)-2-[[(2,3,4,5,6-pentafluorophenoxy)-phenoxy-phosphoryl]amino]propanoate [ No CAS ]
  • [ 6741-73-7 ]
  • C21H28N3O9PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(4-thio-β-D-ribofuransoyl)uracil With tert-butylmagnesium chloride In tetrahydrofuran at -5 - 20℃; for 1h; Inert atmosphere; Stage #2: isopropyl (2R)-2-[[(2,3,4,5,6-pentafluorophenoxy)-phenoxy-phosphoryl]amino]propanoate In tetrahydrofuran at -5 - 20℃; for 120h; Inert atmosphere; To a solution of thiouridine (0.384 mmol) in THF (10 mE/mmol) at -5° C. under nitrogen was added dropwise tert-butylmagnesium chloride (1M in THF) (0.798 mmol). The heterogeneous reaction mixture was stirred during 30 minutes at -5° C. and 30 minutes at 20° C. The reaction mixture was cooled down to -5° C. under nitrogen and appropriate compound A-3a, A-3b, orA-3c (0.456 mmol) in THF (10 mE/mmol) was added dropwise. The reaction mixture was abandoned at room temperature during 5 days. The reaction mixture was quenched with aqueous solution of HC1 2N and diluted with toluene. The organic layer was washed with H20, Na2CO3 2N and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluent: DCM/MeOH 0 to 10%) and by preparative HPEC to give the compound as a mixture of two diastereoisomers or as a pure diastereoisomer. A-3a to give a mixture of diastereoisomers.10328] 16% yield; white solid; ‘H NMR (DMSO-d5, 400MHz) ö (ppm) 1.14 (d, J=6.23 Hz, 3H), 1.15 (d, J=6.23 Hz,3H), 1.20 (d, J=7.13 Hz, 3H), 3.39-3.44 (m, 1H), 3.71-3.82(m, 1H), 4.03-4.08(m, 1H), 4.11-4.25 (m, 2H), 4.27-4.36(m,1H), 4.85 (heptuplet, J=6.24 Hz, 1H), 5.48-5.50 (m, 1H),5.60-5.64 (m, 2H), 5.90-5.93 (m, 1H), 5.97-6.04 (m, 1H),7.15-7.23 (m, 3H), 7.34-7.39 (m, 2H), 7.91-7.96 (m, 1H),11.36 (s, 1H); 3’P NMR (DMSO-d5, 161.98 MHz) ö (ppm)3.16 (s, 0.2P), 3.53 (s, 0.8P); MS (ESI) m/z=530.2 (MHj.10327] Compound 2a was synthesized from compound
Reference： [1]Current Patent Assignee: MERCK & CO INC - US2014/364446, 2014, A1 Location in patent: Paragraph 0325; 0326; 0327; 0328
  • 36
  • [ 6741-73-7 ]
  • 2-(2,2-dimethylpropanoylsulfanyl)ethoxy phosphinic acid [ No CAS ]
  • C16H25N2O8PS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; pivaloyl chloride at 0℃; for 1h; Inert atmosphere; To a solution of 1’,4’-thiouridine (1.92 mmol) and H-phosphonate (2.88 mmol) in pyridine (15 mE) at 0° C. under nitrogen was added dropwise pivaloyl chloride (3.84 mmol). The reaction mixture was stirred at 0° C. during 1 hour. The mixture was added to a stirring NH4C1 1M solution and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2504, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (eluent: DCM/MeOH 0 to 10%). A part of purified intermediate (0.19 mmol) was dissolved with dichloromethane (10 mE) and CC14 (5 mE). Amine or aminoester hydrochloride (0.57 mmol) was added (and Et3N in the case of aminoester hydrochloride (0.95 mmol)) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was purified directly by chromatography on silica gel (eluent: DCMJ MeOH 0 to 5%) and by preparative HPLC to give a mixture of two diastereoisomers or pure diastereoisomers.
Reference： [1]Current Patent Assignee: MERCK & CO INC - US2014/364446, 2014, A1 Location in patent: Paragraph 0346
  • 37
  • (2R,3R,4R)-2-Mercaptomethyl-5-methoxy-tetrahydro-furan-3,4-diol [ No CAS ]
  • [ 6741-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: hydrogenchloride / methanol 2: toluene-4-sulfonic acid 3: triethylamine 4: water; sodium tetrahydroborate 5: 1H-imidazole 6: 3-chloro-benzenecarboperoxoic acid 7: trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine 8: DOWEX 50WX8
Reference： [1]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
  • 38
  • [ 18162-48-6 ]
  • [ 6741-73-7 ]
  • 2',3',5'-tris-O-(tert-butyldimethylsilyl)-4'-deoxy-4'-thiouridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 11h;
Reference： [1]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
  • 39
  • [ 6741-73-7 ]
  • C11H15N3O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 3: dichloro-acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide / 27 h / 20 °C 4: acetic acid; water / tetrahydrofuran / 10 h / 20 °C 5: NAD; potassium chloride; D,L-dithiothreitol; recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent transaldolase; aldehyde dehydrogenase / aq. buffer / 9 h / 20 °C / pH 7.5 / Enzymatic reaction
Multi-step reaction with 6 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 3: dichloro-acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide / 27 h / 20 °C 4: acetic acid; water / tetrahydrofuran / 10 h / 20 °C 5: recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent transaldolase; recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase / aq. buffer / 20 h / 20 °C / pH 7.5 6: recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase; pyridoxal 5'-phosphate / aq. buffer / 20 °C / pH 7.5
Multi-step reaction with 8 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / [D3]acetonitrile / 5 h / 55 °C 4: dichloromethane / 2 h / 0 °C 5: tetrabutylammoniun azide / N,N-dimethyl-formamide / 2 h / 20 °C 6: trifluoroacetic acid / water / 1 h / 20 °C 7: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C 8: recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase; pyridoxal 5'-phosphate / aq. buffer / 20 °C / pH 7.5
Reference： [1]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
[2]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
[3]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
  • 40
  • [ 6741-73-7 ]
  • C12H13N3O8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 3: dichloro-acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide / 27 h / 20 °C 4: acetic acid; water / tetrahydrofuran / 10 h / 20 °C 5: NAD; potassium chloride; D,L-dithiothreitol; recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent transaldolase; aldehyde dehydrogenase / aq. buffer / 9 h / 20 °C / pH 7.5 / Enzymatic reaction 6: potassium hydroxide / water; toluene / 0.5 h / 0 °C
Multi-step reaction with 7 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 3: dichloro-acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide / 27 h / 20 °C 4: acetic acid; water / tetrahydrofuran / 10 h / 20 °C 5: recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent transaldolase; recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase / aq. buffer / 20 h / 20 °C / pH 7.5 6: recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase; pyridoxal 5'-phosphate / aq. buffer / 20 °C / pH 7.5 7: potassium hydroxide / water; toluene / 0.5 h / 0 °C
Multi-step reaction with 9 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / [D3]acetonitrile / 5 h / 55 °C 4: dichloromethane / 2 h / 0 °C 5: tetrabutylammoniun azide / N,N-dimethyl-formamide / 2 h / 20 °C 6: trifluoroacetic acid / water / 1 h / 20 °C 7: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C 8: recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase; pyridoxal 5'-phosphate / aq. buffer / 20 °C / pH 7.5 9: potassium hydroxide / water; toluene / 0.5 h / 0 °C
Reference： [1]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
[2]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
[3]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
  • 41
  • [ 6741-73-7 ]
  • C11H14(2)HN3O7S [ No CAS ]
  • C11H14(2)HN3O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 3: dichloro-acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide / 27 h / 20 °C 4: acetic acid; water / tetrahydrofuran / 10 h / 20 °C 5: NAD; potassium chloride; D,L-dithiothreitol; recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent transaldolase; aldehyde dehydrogenase / aq. buffer / 9 h / 20 °C / pH 7.5 / Enzymatic reaction 6: water-d2; recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase / Enzymatic reaction
Multi-step reaction with 7 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 3: dichloro-acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide / 27 h / 20 °C 4: acetic acid; water / tetrahydrofuran / 10 h / 20 °C 5: recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent transaldolase; recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase / aq. buffer / 20 h / 20 °C / pH 7.5 6: recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase; pyridoxal 5'-phosphate / aq. buffer / 20 °C / pH 7.5 7: water-d2; recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase / Enzymatic reaction
Multi-step reaction with 9 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / [D3]acetonitrile / 5 h / 55 °C 4: dichloromethane / 2 h / 0 °C 5: tetrabutylammoniun azide / N,N-dimethyl-formamide / 2 h / 20 °C 6: trifluoroacetic acid / water / 1 h / 20 °C 7: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C 8: recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase; pyridoxal 5'-phosphate / aq. buffer / 20 °C / pH 7.5 9: water-d2; recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase / Enzymatic reaction
Reference： [1]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
[2]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
[3]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
  • 42
  • [ 6741-73-7 ]
  • 2',3'-bis-O-(triethylsilyl)-4'-deoxy-4'-thiouridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C
Reference： [1]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
  • 43
  • [ 6741-73-7 ]
  • C21H38N2O5SSi2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 3: dichloro-acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide / 27 h / 20 °C
Reference： [1]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
  • 44
  • [ 6741-73-7 ]
  • 2',3'-bis-O-(tert-butyldimethylsilyl)-4'-deoxy-4'-thiouridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
Reference： [1]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
  • 45
  • [ 6741-73-7 ]
  • C11H15N3O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C 3: dichloro-acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide / 27 h / 20 °C 4: acetic acid; water / tetrahydrofuran / 10 h / 20 °C 5: recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent transaldolase; recombinant N-His<SUB>6</SUB>-tagged pyridoxal 5'-phosphate dependent epimerase / aq. buffer / 20 h / 20 °C / pH 7.5
Multi-step reaction with 7 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / [D3]acetonitrile / 5 h / 55 °C 4: dichloromethane / 2 h / 0 °C 5: tetrabutylammoniun azide / N,N-dimethyl-formamide / 2 h / 20 °C 6: trifluoroacetic acid / water / 1 h / 20 °C 7: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C
Reference： [1]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
[2]Ushimaru, Richiro; Liu, Hung-Wen [Journal of the American Chemical Society, 2019]
  • 46
  • [ 6741-73-7 ]
  • [ 26527-35-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Sodium hydrogenocarbonate; bis(phenyl) carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 2: potassium hydroxide; water monomer; methanol / ethanol / 18.17 h / 20 °C
Multi-step reaction with 2 steps 1: Sodium hydrogenocarbonate; bis(phenyl) carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 2: potassium hydroxide / ethanol; water monomer / 18 h / 20 °C
Reference： [1]Guinan, Mieke; Hawes, Chris S.; Huang, Ningwu; Lima, Marcelo A.; Miller, Gavin J.; Smith, Mark [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1401 - 1406]
[2]Guinan, Mieke; Hawes, Chris S.; Huang, Ningwu; Lima, Marcelo A.; Miller, Gavin J.; Smith, Mark [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1401 - 1406]
  • 47
  • [ 6741-73-7 ]
  • 2’,3’,5’-tri-O-acetyl-1’-β-(4’-thio-D-arabinofuranosyl)uracil [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Sodium hydrogenocarbonate; bis(phenyl) carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 2: potassium hydroxide; water monomer; methanol / ethanol / 18.17 h / 20 °C 3: pyridine / 22 h / 20 °C
Multi-step reaction with 3 steps 1: Sodium hydrogenocarbonate; bis(phenyl) carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 2: potassium hydroxide / ethanol; water monomer / 18 h / 20 °C 3: pyridine / 22 h / 20 °C
Reference： [1]Guinan, Mieke; Hawes, Chris S.; Huang, Ningwu; Lima, Marcelo A.; Miller, Gavin J.; Smith, Mark [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1401 - 1406]
[2]Guinan, Mieke; Hawes, Chris S.; Huang, Ningwu; Lima, Marcelo A.; Miller, Gavin J.; Smith, Mark [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1401 - 1406]
  • 48
  • [ 6741-73-7 ]
  • 2’,3’,5’-O-tri-acetyl-4-C-(1,2,4-triazole)-1’-β-(4’-thio-D-arabinofuranosyl)uracil [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Sodium hydrogenocarbonate; bis(phenyl) carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 2: potassium hydroxide; water monomer; methanol / ethanol / 18.17 h / 20 °C 3: pyridine / 22 h / 20 °C 4: triethylamine; trichlorophosphate / acetonitrile / 3 h / 0 - 20 °C
Multi-step reaction with 4 steps 1: Sodium hydrogenocarbonate; bis(phenyl) carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 2: potassium hydroxide / ethanol; water monomer / 18 h / 20 °C 3: pyridine / 22 h / 20 °C 4: triethylamine; trichlorophosphate / acetonitrile / 3 h / 0 - 20 °C
Reference： [1]Guinan, Mieke; Hawes, Chris S.; Huang, Ningwu; Lima, Marcelo A.; Miller, Gavin J.; Smith, Mark [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1401 - 1406]
[2]Guinan, Mieke; Hawes, Chris S.; Huang, Ningwu; Lima, Marcelo A.; Miller, Gavin J.; Smith, Mark [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1401 - 1406]
  • 49
  • [ 6741-73-7 ]
  • [ 26599-17-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Sodium hydrogenocarbonate; bis(phenyl) carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 2: potassium hydroxide; water monomer; methanol / ethanol / 18.17 h / 20 °C 3: pyridine / 22 h / 20 °C 4: triethylamine; trichlorophosphate / acetonitrile / 3 h / 0 - 20 °C 5: ammonia; methanol / 24 h / 120 °C / Sealed tube
Multi-step reaction with 5 steps 1: Sodium hydrogenocarbonate; bis(phenyl) carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 2: potassium hydroxide / ethanol; water monomer / 18 h / 20 °C 3: pyridine / 22 h / 20 °C 4: triethylamine; trichlorophosphate / acetonitrile / 3 h / 0 - 20 °C 5: ammonia; methanol / 24 h / 120 °C / Sealed tube
Reference： [1]Guinan, Mieke; Hawes, Chris S.; Huang, Ningwu; Lima, Marcelo A.; Miller, Gavin J.; Smith, Mark [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1401 - 1406]
[2]Guinan, Mieke; Hawes, Chris S.; Huang, Ningwu; Lima, Marcelo A.; Miller, Gavin J.; Smith, Mark [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1401 - 1406]
  • 50
  • [ 6741-73-7 ]
  • 1’-(4’-sulfinyl(S,R)-D-arabinofuranosyl)cytosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: Sodium hydrogenocarbonate; bis(phenyl) carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 2: potassium hydroxide; water monomer; methanol / ethanol / 18.17 h / 20 °C 3: pyridine / 22 h / 20 °C 4: triethylamine; trichlorophosphate / acetonitrile / 3 h / 0 - 20 °C 5: ammonia; methanol / 24 h / 120 °C / Sealed tube 6: 3-chloro-benzenecarboperoxoic acid / acetonitrile; water monomer / 20 h / 0 - 20 °C
Multi-step reaction with 6 steps 1: Sodium hydrogenocarbonate; bis(phenyl) carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 2: potassium hydroxide / ethanol; water monomer / 18 h / 20 °C 3: pyridine / 22 h / 20 °C 4: triethylamine; trichlorophosphate / acetonitrile / 3 h / 0 - 20 °C 5: ammonia; methanol / 24 h / 120 °C / Sealed tube 6: 3-chloro-benzenecarboperoxoic acid / acetonitrile; water monomer / 20 h / 0 - 20 °C
Reference： [1]Guinan, Mieke; Hawes, Chris S.; Huang, Ningwu; Lima, Marcelo A.; Miller, Gavin J.; Smith, Mark [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1401 - 1406]
[2]Guinan, Mieke; Hawes, Chris S.; Huang, Ningwu; Lima, Marcelo A.; Miller, Gavin J.; Smith, Mark [Organic and Biomolecular Chemistry, 2022, vol. 20, # 7, p. 1401 - 1406]
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