Name: 68892-41-1|N2-Isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine|95%
Brand: Ambeed
SKU: A135681
Price: 5.0 USD
Availability: InStock
Rating: 91 (40 reviews)

1
[ 108-30-5 ]
[ 68892-41-1 ]
[ 74405-46-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With dmap In pyridine
	With pyridine; dmap; triethylamine In dichloromethane for 4h; Ambient temperature;

Reference： [1]Le Bec, Christine; Wickstrom, Eric [Tetrahedron Letters, 1994, vol. 35, # 51, p. 9525 - 9528]
[2]Matsuzaki, Jun-ichi; Kohno, Kyoko; Tahara, Shin-ichiro; Sekine, Mitsuo; Hata, Tsujiaki [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 4, p. 1407 - 1414]

2
[ 68892-42-2 ]
[ 40615-36-9 ]
[ 68892-41-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With pyridine; at 20℃; for 5h;	Step 2-2N-Isobutyryl-5'O-Dimetoxytrityl deoxyguanosine (B5-II)2N-Isobutyryl deoxyguanosine (B5-I) was dried by co-evaporation with dry pyridine three times. To a stirred suspension of dry (B5-I) (14.15 mmol) in pyridine (100 mL), a solution of dimetoxytrityl chloride (14.8 mmol) in pyridine (30 mL) was added dropwise over a period of 60 min. The reaction mixture was left for 4 h at room temperature, cooled to 0 C. by immersion in an ice water bath, quenched with 5% NaHCO3 (100 mL), and extracted with ethyl acetate (3×100 mL). The organic fractions were pooled, dried over magnesium sulfate, concentrated in vacuum and the residue was co-evaporated with toluene. The gum oil residue was dissolved in a minimum amount of methylenechloride and added dropwise to a mixture of ethyl ether and petroleum ether (2000 mL 75/25) with stirring. After 20 min, pure 2N-Isobutyryl-5'O-Dimetoxytrityl deoxyguanosine precipitated from the solution and was filtered off and dried.Yield: 75%

Reference： [1]Synthesis,1983,p. 540 - 541
[2]Synthesis,1984,p. 965 - 968
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 370 - 371
[4]Helvetica Chimica Acta,1982,vol. 65,p. 2372 - 2393
[5]Patent: US2011/86813,2011,A1 .Location in patent: Page/Page column 34
[6]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1993,vol. 32,p. 916 - 919
[7]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1996,vol. 35,p. 657 - 661
[8]Organic and Biomolecular Chemistry,2012,vol. 10,p. 1510 - 1513

3
[ 5666-12-6 ]
[ 68892-41-1 ]
[ 1055040-37-3 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 2377 - 2388

4
[ 13154-24-0 ]
[ 68892-41-1 ]
[ 136198-19-1 ]

Yield	Reaction Conditions	Operation in experiment
78.8%	With 1H-imidazole In N,N-dimethyl-formamide for 24h; Ambient temperature;

Reference： [1]Sood; Shaw; Spielvogel; Hall; Chi; Hall [Pharmazie, 1992, vol. 47, # 11, p. 833 - 838]

5
[ 3348-44-5 ]
[ 68892-41-1 ]
C₃₉H₄₈N₇O₇P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In acetonitrile

Reference： [1]Brill, Wolfgang K.-D.; Tang, Jin-Yan; Ma, Yun-Xi; Caruthers, Marvin H. [Journal of the American Chemical Society, 1989, vol. 111, # 6, p. 2321 - 2322]

6
[ 59274-18-9 ]
[ 68892-41-1 ]
[ 84432-75-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Ambient temperature;

Reference： [1]Adams, Steven P.; Kavka, Kamila S.; Wykes, Evan J.; Holder, Sarah B.; Galluppi, Gerald R. [Journal of the American Chemical Society, 1983, vol. 105, # 3, p. 661 - 663]

7
[ 66470-81-3 ]
[ 68892-41-1 ]
[ 120942-92-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	With pyridine In dichloromethane for 0.25h;

Reference： [1]Watanabe, Tetsuo; Sato, Hirotaka; Takaku, Hiroshi [Journal of the American Chemical Society, 1989, vol. 111, # 9, p. 3437 - 3439]

8
[ 70063-12-6 ]
[ 68892-41-1 ]
[ 78635-94-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Ambient temperature;

Reference： [1]Adams, Steven P.; Kavka, Kamila S.; Wykes, Evan J.; Holder, Sarah B.; Galluppi, Gerald R. [Journal of the American Chemical Society, 1983, vol. 105, # 3, p. 661 - 663]

9
[ 63135-66-0 ]
[ 68892-41-1 ]
[ 1055040-37-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In acetonitrile

Reference： [1]Brill, Wolfgang K.-D.; Tang, Jin-Yan; Ma, Yun-Xi; Caruthers, Marvin H. [Journal of the American Chemical Society, 1989, vol. 111, # 6, p. 2321 - 2322]

10
[ 68892-41-1 ]
[ 124482-92-4 ]
5'-O-dimethoxytrityl-N₂-isobutyryl-2'-deoxyguanosine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 65℃; for 0.25h; Inert atmosphere; Microwave irradiation; Sealed tube;
	In tetrahydrofuran according to ref 3) with modifications;

Reference： [1]Meher; Efthymiou; Stoop; Krishnamurthy [Chemical Communications, 2014, vol. 50, # 56, p. 7463 - 7465]
[2]Sinha, N. D.; Biernat, J.; Koester, H. [Tetrahedron Letters, 1983, vol. 24, # 52, p. 5843 - 5846]

11
[ 68892-41-1 ]
[ 86030-43-5 ]
[ 84416-84-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Ambient temperature;

Reference： [1]Adams, Steven P.; Kavka, Kamila S.; Wykes, Evan J.; Holder, Sarah B.; Galluppi, Gerald R. [Journal of the American Chemical Society, 1983, vol. 105, # 3, p. 661 - 663]

12
[ 68892-41-1 ]
[ 75302-66-8 ]
[ 114360-61-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h;

Reference： [1]Uznanski, Bogdan; Wilk, Andrzej; Stec, Wojciech J. [Tetrahedron Letters, 1987, vol. 28, # 29, p. 3401 - 3404]

13
[ 68892-41-1 ]
[ 91876-63-0 ]
[ 125190-10-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.25h;

Reference： [1]Beiter; Pfleiderer [Synthesis, 1989, # 7, p. 497 - 500]
[2]Beiter, A. H.; Pfleiderer, W. [Tetrahedron Letters, 1984, vol. 25, # 19, p. 1974 - 1978]

14
[ 68892-41-1 ]
[ 96404-99-8 ]
[ 80817-36-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1-methyl-1H-imidazole; 2,4,6-triisopropylphenylsulfonyl chloride In pyridine for 0.5h;

Reference： [1]Yamada, Kohji; Dohmori, Renzo [Synthesis, 1984, # 4, p. 333 - 335]

15
[ 68892-41-1 ]
[ 86979-44-4 ]
[ 86979-49-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole In pyridine for 1h; Ambient temperature;

Reference： [1]Vasseur, J.J.; Rayner, B.; Imbach, J.L. [Tetrahedron Letters, 1983, vol. 24, # 27, p. 2753 - 2756]

16
[ 68892-41-1 ]
[ 108787-34-4 ]
[ 136340-78-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 1H-tetrazole In 1,4-dioxane; acetonitrile at 20℃; for 1h;

Reference： [1]Roelen, H. C. P. F.; Kamer, P. C. J.; Elst, H. van den; Marel, G. A. van der; Boom, J. H. van [Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 7-8, p. 325 - 331]

17
[ 68892-41-1 ]
[ 93636-01-2 ]
[ 98293-12-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With 1-methyl-1H-imidazole In tetrahydrofuran for 0.75h;

Reference： [1]Tsuchiya, Hiromichi; Ueda, Souichi; Kobayashi, Hitoshi; Takaku, Hiroshi [Chemistry Letters, 1985, p. 347 - 350]

18
[ 68892-41-1 ]
[ 139063-18-6 ]
[ 142721-39-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine In dichloromethane

Reference： [1]Huie, Edward M.; Kirshenbaum, Mindy R.; Trainor, George L. [Journal of Organic Chemistry, 1992, vol. 57, # 17, p. 4569 - 4570]

19
[ 68892-41-1 ]
[ 81087-19-6 ]
[ 84354-71-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1-methyl-1H-imidazole In acetonitrile at 25℃; for 4.5h;

Reference： [1]Ohtsuka; Shibahara; Ikehara [Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 12, p. 3440 - 3448]

20
[ 68892-41-1 ]
[ 88734-01-4 ]
Isopropyl-methyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In tetrahydrofuran Ambient temperature;

Reference： [1]Adams, Steven P.; Kavka, Kamila S.; Wykes, Evan J.; Holder, Sarah B.; Galluppi, Gerald R. [Journal of the American Chemical Society, 1983, vol. 105, # 3, p. 661 - 663]

21
[ 68892-41-1 ]
[ 68892-42-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In methanol; dichloromethane; at 0℃; for 1h;	Compound 48, N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenyl- methoxy]methyl]-4-hydroxy-tetrahydrofuran-2-yl]-6-oxo-lH-purin-2-yl]-2 -methyl-propanamide (50.0 g, 78.2 mmol) was dissolved in DCM/Methanol (1560 mL) and cooled to 0C. Sodium carbonate (9.94 g, 93.8 mmol) was added and the orange reaction mixture was stirred at 0C. After 60 minutes sodium carbonate (9.94 g, 93.8 mmol) was added at 0C and stirred until the orange color disappeared. The solvents were removed under reduced pressure. Dichloromethane was added to the crude reaction and the white precipitate was isolated and dried under high vacuum. The crude desired product was isolated as a white solid. (28.7 g, 85.1 mmol, yield: 109 %)

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 6021 - 6022
[2]Tetrahedron,1991,vol. 47,p. 2377 - 2388
[3]Tetrahedron Letters,1995,vol. 36,p. 7833 - 7836
[4]Collection of Czechoslovak Chemical Communications,2002,vol. 67,p. 502 - 508
[5]Patent: WO2020/72991,2020,A1 .Location in patent: Page/Page column 87-88

22
[ 68892-41-1 ]
[ 81144-43-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With ammonium hydroxide In 1,4-dioxane for 72h;
94%	With methanol; 1,8-diaza[5.4.0]undec-7-ene In 1,4-dioxane at 50℃; for 5h;

Reference： [1]Gryaznov; Schultz [Tetrahedron Letters, 1994, vol. 35, # 16, p. 2489 - 2492]
[2]Roelen, H. C. P. F.; Brugghe, H. F.; Elst, H. van den; Marel, G. A. van der; Boom, J. H. van [Recueil des Travaux Chimiques des Pays-Bas, 1992, vol. 111, # 2, p. 99 - 104]

23
[ 68892-41-1 ]
[ 115131-08-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.333333h; Ambient temperature;

Reference： [1]Agrawal, Sudhir; Goodchild, John [Tetrahedron Letters, 1987, vol. 28, # 31, p. 3539 - 3542]

24
[ 68892-41-1 ]
[ 100205-38-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triphenylphosphine; diethylazodicarboxylate In 1,4-dioxane for 0.5h;

Reference： [1]Gao, Xiaolian; Gaffney, Barbara L.; Hadden, Susan; Jones, Roger A. [Journal of Organic Chemistry, 1986, vol. 51, # 5, p. 755 - 758]

25
[ 68892-41-1 ]
N-(9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-8-bromo-6-oxo-6,9-dihydro-1H-purin-2-yl)-isobutyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With bromine; sodium acetate In 1,4-dioxane

Reference： [1]Dias; Battiste; Williamson [Journal of the American Chemical Society, 1994, vol. 116, # 10, p. 4479 - 4480]

26
[ 68892-41-1 ]
[ 108-24-7 ]
[ 93130-36-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	In pyridine at 20℃; for 1h;
85%	In pyridine for 2h; Ambient temperature;
85%	With pyridine at 20℃; for 2h;

With pyridine

Reference： [1]Chollet, Andre; Ayala, Edgar; Kawashima, Eric H. [Helvetica Chimica Acta, 1984, vol. 67, p. 1356 - 1364]
[2]Awasthi, S. K.; Khanna, V.; Watal, G.; Misra, K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 9, p. 916 - 919]
[3]Kumar, Prabhat; Singh; Misra [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 7, p. 657 - 661]
[4]Lesiak, Krystyna; Watanabe, Kyoichi A.; George, Jay; Pankiewicz, Krzysztof W. [Journal of Organic Chemistry, 1998, vol. 63, # 6, p. 1906 - 1909]

27
[ 68892-41-1 ]
[ 123-76-2 ]
[ 86710-51-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In 1,4-dioxane for 1h;
	With dmap; dicyclohexyl-carbodiimide In 1,4-dioxane at 25℃; for 3h;

Reference： [1]Kumar, G.; Poonian, M.S. [Journal of Organic Chemistry, 1984, vol. 49, # 25, p. 4905 - 4912]
[2]Marchan, Vicente; Cieslak, Jacek; Livengood, Victor; Beaucage, Serge L. [Journal of the American Chemical Society, 2004, vol. 126, # 31, p. 9601 - 9610]

28
[ 68892-41-1 ]
[ 93-97-0 ]
[ 93966-65-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With dmap; triethylamine In dichloromethane for 3h; Ambient temperature;

Reference： [1]Matsuzaki, Jun-ichi; Hotoda, Hitoshi; Sekine, Mitsuo; Hata, Tsujiaki; Higuchi, Shigesada; et al. [Tetrahedron, 1986, vol. 42, # 2, p. 501 - 514]

29
5'-dimethoxytrityl N²-isobutyryl deoxyguanosine 3'-methylphosphinate [ No CAS ]
[ 68892-41-1 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrabutyl ammonium fluoride In tetrahydrofuran; water for 3h; Ambient temperature;

Reference： [1]Brill, Wolfgang K.-D. [Tetrahedron Letters, 1994, vol. 35, # 19, p. 3041 - 3044]

30
[ 160107-22-2 ]
[ 68892-41-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	With 1H-imidazole In methanol for 72h; Ambient temperature;

Reference： [1]Brill, Wolfgang K.-D. [Tetrahedron Letters, 1994, vol. 35, # 19, p. 3041 - 3044]

31
[ 68892-41-1 ]
[ 18162-48-6 ]
[ 152343-98-1 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium 1.) THF, -20 deg C, 20 min, 2.) THF, RT, 2 h; Multistep reaction;
	With pyridine; silver nitrate In tetrahydrofuran at 20℃;
110 g	With pyridine; 1H-imidazole for 18h;	To dry 5’-O-(4,4’dimethoxytrityl)- N2- (isobutyryl)deoxyguanosine (100 g, 156 mM) was added imidazole (40 g, 0.588 M) in 1200 mL dry pyridine and 100 g (0.666 M) tertbutyldiinethylsilyl chloride. The solution was stirred for 18 hrs, the pyridine was removed by rotary evaporation, and the residue was dissolved in 700 mL of ethyl acetate. The organic phase was washed with 500 ml of 0.5 M K2HPO4 followed by 500 mL saturated NaHCO3. Drying produced 110 g (145 mM) of product 5’-O-(4,4’dimethoxytrityl)- N2- (isobutyryl)-3’-O-tert- butyldimethylsilyl-deoxyguanosine. A solution of the product in 1500 mL of methanol was prepared, and to this was added 150 mL of conc. aqueous ammonia. After brief swirling, the solution was allowed to stand overnight. The solvents were removed by rotary evaporation, and the dried solid was re-dissolved in 1400 mL of THF and 40 g of dry K2C03 were added. After 10 mm of stirring, 100 g di-tert-butyl pyrocarbonate was added. The solution was stirred for 3 hrs. TLC showed partial conversion (silica, 2 % MeOH, 2% pyridine in DCM, if starting material 0.3, rf product 0.7, visualized with 10 % H2S04 and heating). Longer reaction times gave less desired product and more side reaction materials. The K2C03 was removed by filtration and 400 mL of 0.5 M KH2PO4 was added. The THF was removed by rotary evaporation and the residue was mixed with 700 mL DCM. The organic phase was added to a silica column, 10 X 35 cm, packed with 2% methanol and 2% pyridine in DMF. A gradient to 10 % methanol was applied to the column over 14 L of solvent, and fractions containing pure 5’-O-DMT-3’-O- tertbutyldimethylsilyl- N2-(tert-butyloxycarbonyl)-deoxyguanosine were pooled and reduced by rotory evaporation. The yield was 25 g (34 mM, 22% yield from DMT dG(iBu)). The TBDMS group was removed by adding a solution of 60 mL 1 M TBAF in THF and 10 mL of HOAc in 500 mL of THF. After 18 hrs, saturated NaHCO3, 50 mL, was added and the THF was removed by rotary evaporation. The residue was dissolved in 600 mL DCM and washed with 400 mL saturated NaHCO3. The organic phase was reduced to a foam by rotary evaporation to give 5’-O- DMT-N2--(tert-butyloxycarbonyl)-deoxyguanosine (19.5 g, 29.1 mM, 86 % from 5’-O-DMT-3’- 0- tert-butyldimethylsilyl- N2 -(tert-butyloxycarbonyl)-deoxyguanosine). The material was pure enough for the next step. An analytical sample was prepared by column chromatography as above on a silica column, 10 X 35 cM, packed with 2% methanol and 2% pyridine in DCM. A gradient to 10% methanol was applied to the column over 10 L of solvent, and fractions containing pure product were pooled and evaporated. ‘H NMR (400 mHz, CDC13, PPM) 7.7 (m, 1H), 7.2- 7.4 (m, 1OH), 6.8 (d, 4H), 6.2 (t, 1H), 5.7 (s, 2H), 4.65 (m, 1H), 4.15 (m, 1H), 3.8 (s, 6H), 3.35 (m, 2H), 2.7 (m, 1H), 2.45 (m, 1H), 1.6 (s, 18Ff).

	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 20h;	30 First, from Compound 73 (Nucleoside & Nucleotide, 1985, 4, 641-649)Compound 74(9 - (3 - O - tert - butyldimethylsilyl - 2 - O - deoxy - β - D - ribofuranosyl) - 1 - hydro - 2 - isobutyrylamino - 6 H - purin - 6 -Was synthesized. That is, after dissolving the compound 73 (8.33 g, 13 mmol) in N, N-dimethylformamide (65 mL), imidazole (2.83 g, 42 mmol) and tert-butyldimethylsilyl chloride (5.89 g, 39 mmol) Sequentially,And the mixture was stirred at room temperature for 20 hours. After completion of the reaction, quenching was carried out with a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate.Subsequently, the organic layer was dried with magnesium sulfate and the solvent was distilled off under reduced pressure,A crude 3 'hydroxyl group protected compound (13 mmol) was obtained.The roughly purified 3 'hydroxyl protected product (13 mmol) was dissolved in chloroform (87 mL), and then p-toluenesulfonic acid monohydrate (7.42 g, 39 mmol) dissolved in methanol (37 mL) was heated at -15 ° C. , And the mixture was stirred at the same temperature for 1.5 hours.After completion of the reaction, saturated sodium bicarbonate water was added until the reaction solution became colorless from orange,Extraction with chloroform was performed.After drying the organic layer with magnesium sulfate and distilling off the solvent under reduced pressure,The residue was purified by silica gel column chromatography (ethyl acetate / n-hexane = 1/1 → ethyl acetate → methanol / chloroform = 1/20) to give compound 74 (5.44 g, 12 mmol, 2 stepsAbout 93%).
	With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 72h;

Reference： [1]Patil, Sucheta V.; Mane, Ramchandra B.; Salunkhe, Manikrao M. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 1, p. 1 - 2]
[2]Janczyk, Matthaeus; Appel, Bettina; Springstubbe, Danilo; Fritz, Hans-Joachim; Mueller, Sabine [Organic and Biomolecular Chemistry, 2012, vol. 10, # 8, p. 1510 - 1513]
[3]Current Patent Assignee: LGC LIMITED - WO2015/167620, 2015, A1 Location in patent: Page/Page column 113; 114
[4]Current Patent Assignee: KUMAMOTO UNIVERSITY; YAMASA CORPORATION; NATIONAL CENTER FOR GLOBAL HEALTH AND MEDICINE - JP2017/57200, 2017, A Location in patent: Paragraph 0195-0196
[5]Baran, Phil S.; Eastgate, Martin D.; Knouse, Kyle W.; Padial, Natalia M.; Rivas-Bascón, Nazaret; Schmidt, Michael A.; Vantourout, Julien C.; Xu, Dongmin; Zheng, Bin [Journal of the American Chemical Society, 2020]

32
[ 68892-41-1 ]
[ 121-44-8 ]
[ 118352-76-4 ]

Yield	Reaction Conditions	Operation in experiment
33.8%	With bis(trichloromethyl) carbonate; phosphonic acid In acetonitrile at 0℃; for 4h;

Reference： [1]Bhongle, Nandkumar N.; Tang, Jin Yan [Tetrahedron Letters, 1995, vol. 36, # 38, p. 6803 - 6806]

33
[ 68892-41-1 ]
monochloro-N,N-isopropylamino-octylphosphine [ No CAS ]
[R_P/S_P]-5'-O-(4,4'-dimethoxytrityl)-N²-isobutanoyl-2'-deoxyguanosine-3'-O-(N,N-diisopropylamino,n-octyl)-phosphine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Ambient temperature;

Reference： [1]Mag, Matthias; Jahn, Kerstin; Kretzschmar, Gerhard; Peyman, Anusch; Uhlmann, Eugen [Tetrahedron, 1996, vol. 52, # 30, p. 10011 - 10024]

34
[ 68892-41-1 ]
[ 198637-74-0 ]
[ 212575-01-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In acetonitrile for 0.0833333h; Ambient temperature;
	With N-ethyl-N,N-diisopropylamine In acetonitrile for 0.0833333h; Ambient temperature;
	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.25h;

Reference： [1]Stec, Wojciech J.; Karwowski, Bolesław; Boczkowska, Małgorzata; Guga, Piotr; Koziołkiewicz, Maria; Sochacki, Marek; Wieczorek, Michał W.; Błaszczyk, Jarosław [Journal of the American Chemical Society, 1998, vol. 120, # 29, p. 7156 - 7167]
[2]Karwowski, Boleslaw; Guga, Piotr; Kobylanska, Anna; Stec, Wojciech J. [Nucleosides and Nucleotides, 1998, vol. 17, # 9-11, p. 1747 - 1759]
[3]Guga, Piotr; Maciaszek, Anna; Stec, Wojciech J. [Organic Letters, 2005, vol. 7, # 18, p. 3901 - 3904]

35
[ 56183-63-2 ]
[ 68892-41-1 ]
[ 133728-85-5 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In acetonitrile at 20℃; for 0.5h;
	With triethylamine In acetonitrile at 20℃; for 0.333333h;
	With triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;

Reference： [1]Eleuteri, Alessandra; Capaldi, Daniel C.; Cole, Douglas L.; Ravikumar, Vasulinga T. [Nucleosides and Nucleotides, 1999, vol. 18, # 8, p. 1879 - 1882]
[2]Current Patent Assignee: IONIS PHARMACEUTICALS - US6335439, 2002, B1 Location in patent: Example 5
[3]Cheruvallath, Zacharia S.; Eleuteri, Alessandra; Turney, Brett; Ravikumar, Vasulinga T. [Organic Process Research and Development, 2006, vol. 10, # 2, p. 251 - 256]

36
[ 68892-41-1 ]
[ 153120-90-2 ]
[ 136340-78-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h;

Reference： [1]Lang, Holger; Gottlieb, Margarete; Schwarz, Michael; Farkas, Silke; Schulz, Bernd S.; Himmelsbach, Frank; Charubala, Ramamurthy; Pfleiderer, Wolfgang [Helvetica Chimica Acta, 1999, vol. 82, # 12, p. 2172 - 2185]

37
[ 108-30-5 ]
[ 68892-41-1 ]
3-[(2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yloxycarbonyl]-propionic acid anion [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine In dichloromethane at 20℃; for 3h;

Reference： [1]Song; Sanghvi [Nucleosides, nucleotides and nucleic acids, 2001, vol. 20, # 4-7, p. 1267 - 1270]

38
[ 68892-41-1 ]
[ 370596-60-4 ]
Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 4-oxo-pentyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With 1H-tetrazole In dichloromethane; acetonitrile

Reference： [1]Wilk, Andrzej; Chmielewski, Marcin K.; Grajkowski, Andrzej; Phillips, Lawrence R.; Beaucage, Serge L. [Tetrahedron Letters, 2001, vol. 42, # 33, p. 5635 - 5639]

39
[ 68892-41-1 ]
[ 411234-03-2 ]
3'-O-(diisopropylamino)phosphinoacetic acid α,α-dimethyl-β-cyanoethyl ester 5'-O-(4,4'-dimethoxytrityl)-N-2-isobutyryl-2'-deoxyguanosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With 1H-tetrazole In dichloromethane at 20℃; for 24h;

Reference： [1]Dellinger, Douglas J.; Sheehan, David M.; Christensen, Nanna K.; Lindberg, James G.; Caruthers, Marvin H. [Journal of the American Chemical Society, 2003, vol. 125, # 4, p. 940 - 950]

40
[ 68892-41-1 ]
[ 121-44-8 ]
O-phenyl H-phosphonothioate (p-chlorobenzyl)thiouronium salt [ No CAS ]
5'-O-dimethoxytrityl-N²-isobutyryl-2'-deoxyadenosine 3'-H-phosphonothioate triethylammonium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With pyridine; tert-butylchlorodiphenylsilane In toluene

Reference： [1]Laven, Gaston; Nilsson, Johan; Stawinski, Jacek [European Journal of Organic Chemistry, 2004, # 24, p. 5111 - 5114]

41
C₁₄H₁₃O₂PSe*C₈H₉ClN₂S [ No CAS ]
[ 68892-41-1 ]
C₄₉H₄₈N₅O₈PSe [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyridine; chlorophosphoric acid diphenyl ester In acetonitrile for 0.166667h;

Reference： [1]Kullberg, Martin; Stawinski, Jacek [Synthesis, 2005, # 10, p. 1668 - 1674]

42
[ 68892-41-1 ]
[ 40615-39-2 ]
N₂-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-3'-O-(N,N-diisopropylamino)[2-[(N-formyl-N-methyl)amino]ethoxy]phosphinyl-2'-deoxyguanosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-tetrazole In acetonitrile at 25℃; for 12h;

Reference： [1]Grajkowski, Andrzej; Wilk, Andrzej; Chmielewski, Marcin K.; Phillips, Lawrence R.; Beaucage, Serge L. [Organic Letters, 2001, vol. 3, # 9, p. 1287 - 1290]

43
[ 68892-41-1 ]
[ 137348-88-0 ]
5'-O-(4,4'-dimethoxytrityl)-N²-isobutyryl-2'-deoxyguanosine 3'-O-[(tert-butyl)-N,N-diisopropylphosphoramidite] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With N,N-diisopropylamine tetrazolide In dichloromethane at 20℃;

Reference： [1]Ferreira, Fernando; Meyer, Albert; Vasseur, Jean-Jacques; Morvan, Francois [Journal of Organic Chemistry, 2005, vol. 70, # 23, p. 9198 - 9206]

44
[ 64350-24-9 ]
[ 68892-41-1 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2004,vol. 23,p. 171 - 181

45
[ 68892-41-1 ]
[ 93134-41-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,3-dicyclohexylcarbodiimide; (N,N-dimethylamino)pyridine / dioxane / 3 h / 25 °C 2: acetic acid / 2 h / 25 °C
	Multi-step reaction with 2 steps 1: 5 h / 20 °C 2: p-toluenesulfonic acid / ethyl acetate; methanol / 20 °C
	Multi-step reaction with 2 steps 1: (N,N-dimethylamino)pyridine, dicyclohexylcarbodiimide / dioxane / 1 h 2: 80 percent acetic acid / 0.5 h

Reference： [1]Marchan, Vicente; Cieslak, Jacek; Livengood, Victor; Beaucage, Serge L. [Journal of the American Chemical Society, 2004, vol. 126, # 31, p. 9601 - 9610]
[2]Eleuteri, Alessandra; Capaldi, Daniel C.; Cole, Douglas L.; Ravikumar, Vasulinga T. [Nucleosides and Nucleotides, 1999, vol. 18, # 3, p. 475 - 483]
[3]Kumar, G.; Poonian, M.S. [Journal of Organic Chemistry, 1984, vol. 49, # 25, p. 4905 - 4912]

46
[ 68892-41-1 ]
[ 753456-27-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 1,3-dicyclohexylcarbodiimide; (N,N-dimethylamino)pyridine / dioxane / 3 h / 25 °C 2.1: acetic acid / 2 h / 25 °C 3.1: triethylamine; thionyl chloride / acetonitrile / 0.17 h / 5 °C 3.2: 83 percent / acetonitrile / 2 h / 25 °C 4.1: 48 percent / hydrazine hydrate; pyridine; acetic acid / 0.05 h / 25 °C

Reference： [1]Marchan, Vicente; Cieslak, Jacek; Livengood, Victor; Beaucage, Serge L. [Journal of the American Chemical Society, 2004, vol. 126, # 31, p. 9601 - 9610]

47
[ 68892-41-1 ]
[ 753456-23-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 1,3-dicyclohexylcarbodiimide; (N,N-dimethylamino)pyridine / dioxane / 3 h / 25 °C 2.1: acetic acid / 2 h / 25 °C 3.1: triethylamine; thionyl chloride / acetonitrile / 0.17 h / 5 °C 3.2: 83 percent / acetonitrile / 2 h / 25 °C

Reference： [1]Marchan, Vicente; Cieslak, Jacek; Livengood, Victor; Beaucage, Serge L. [Journal of the American Chemical Society, 2004, vol. 126, # 31, p. 9601 - 9610]

48
[ 68892-41-1 ]
[ 753456-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 1,3-dicyclohexylcarbodiimide; (N,N-dimethylamino)pyridine / dioxane / 3 h / 25 °C 2.1: acetic acid / 2 h / 25 °C 3.1: triethylamine; thionyl chloride / acetonitrile / 0.17 h / 5 °C 3.2: 83 percent / acetonitrile / 2 h / 25 °C 4.1: 48 percent / hydrazine hydrate; pyridine; acetic acid / 0.05 h / 25 °C 5.1: 54 percent / triethylamine / acetonitrile / 1 h / 25 °C

Reference： [1]Marchan, Vicente; Cieslak, Jacek; Livengood, Victor; Beaucage, Serge L. [Journal of the American Chemical Society, 2004, vol. 126, # 31, p. 9601 - 9610]

49
[ 68892-41-1 ]
N-{9-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(2-oxo-3-oxa-1-thia-2λ⁵-phospha-spiro[4.5]dec-2-yloxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-isobutyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: iPr₂NEt / acetonitrile / 0.08 h / Ambient temperature 2: SeO₂ / acetonitrile / 3 h / Ambient temperature
	Multi-step reaction with 2 steps 1: diisopropylethylamine / acetonitrile / 0.08 h / Ambient temperature 2: 54 percent / SeO₂ / acetonitrile / 3 h / Ambient temperature

Reference： [1]Karwowski, Boleslaw; Guga, Piotr; Kobylanska, Anna; Stec, Wojciech J. [Nucleosides and Nucleotides, 1998, vol. 17, # 9-11, p. 1747 - 1759]
[2]Stec, Wojciech J.; Karwowski, Bolesław; Boczkowska, Małgorzata; Guga, Piotr; Koziołkiewicz, Maria; Sochacki, Marek; Wieczorek, Michał W.; Błaszczyk, Jarosław [Journal of the American Chemical Society, 1998, vol. 120, # 29, p. 7156 - 7167]

50
[ 68892-41-1 ]
[ 883716-66-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diisopropylethylamine / acetonitrile / 0.08 h / Ambient temperature 2: sulfur / acetonitrile / 12 h

Reference： [1]Stec, Wojciech J.; Karwowski, Bolesław; Boczkowska, Małgorzata; Guga, Piotr; Koziołkiewicz, Maria; Sochacki, Marek; Wieczorek, Michał W.; Błaszczyk, Jarosław [Journal of the American Chemical Society, 1998, vol. 120, # 29, p. 7156 - 7167]

51
[ 68892-41-1 ]
5’-O-DMT-O⁶-diphenylcarbamoyl-N²-isobutyryl-2’-deoxyguanosine-3’-O-(2-thio-4,4-pentamethylene-1,3,2-oxathiaphospholane) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: diisopropylethylamine / acetonitrile / 0.08 h / Ambient temperature 2: sulfur / acetonitrile / 12 h 3: 95 percent / pyridine, diisopropylethylamine / 1 h / Ambient temperature

Reference： [1]Stec, Wojciech J.; Karwowski, Bolesław; Boczkowska, Małgorzata; Guga, Piotr; Koziołkiewicz, Maria; Sochacki, Marek; Wieczorek, Michał W.; Błaszczyk, Jarosław [Journal of the American Chemical Society, 1998, vol. 120, # 29, p. 7156 - 7167]

52
[ 68892-41-1 ]
O⁶-[2-(methylnitrosamino)ethyl]-2'-deoxyguanosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: dioxane / 0.25 h 2: diethylazodicarboxylate, triphenylphosphine / dioxane / 1 h / Ambient temperature 3: 1M HF/pyridine / 0.25 h 4: aq. NH₃ / methanol / 10 h / 80 °C 5: 80percent aq. AcOH / 0.5 h / Ambient temperature

Reference： [1]Loeppky, Richard N.; Yu, Li; Gu, Feng; Ye, Qiuping [Journal of the American Chemical Society, 1996, vol. 118, # 45, p. 10995 - 11005]

53
[ 68892-41-1 ]
C₃₄H₃₇N₇O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: dioxane / 0.25 h 2: diethylazodicarboxylate, triphenylphosphine / dioxane / 1 h / Ambient temperature 3: 1M HF/pyridine / 0.25 h 4: aq. NH₃ / methanol / 10 h / 80 °C

Reference： [1]Loeppky, Richard N.; Yu, Li; Gu, Feng; Ye, Qiuping [Journal of the American Chemical Society, 1996, vol. 118, # 45, p. 10995 - 11005]

54
[ 68892-41-1 ]
5'-O-(dimethoxytrityl)-N²-isobutyryl-O⁶-[2-(nitrosaminomethyl)ethyl]-2'-deoxyguanosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dioxane / 0.25 h 2: diethylazodicarboxylate, triphenylphosphine / dioxane / 1 h / Ambient temperature 3: 1M HF/pyridine / 0.25 h

Reference： [1]Loeppky, Richard N.; Yu, Li; Gu, Feng; Ye, Qiuping [Journal of the American Chemical Society, 1996, vol. 118, # 45, p. 10995 - 11005]

55
[ 68892-41-1 ]
[ 184224-53-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dioxane / 0.25 h 2: diethylazodicarboxylate, triphenylphosphine / dioxane / 1 h / Ambient temperature

Reference： [1]Loeppky, Richard N.; Yu, Li; Gu, Feng; Ye, Qiuping [Journal of the American Chemical Society, 1996, vol. 118, # 45, p. 10995 - 11005]

56
[ 68892-41-1 ]
[ 99540-94-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) BuLi / 1.) THF, -20 deg C, 20 min, 2.) THF, RT, 2 h 2: 80percent aq. AcOH / 0.5 h / Ambient temperature
	Multi-step reaction with 2 steps 1: pyridine; silver nitrate / tetrahydrofuran / 20 °C 2: trichloroacetic acid / dichloromethane / 0.17 h / 20 °C
	Multi-step reaction with 2 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 20 h / 20 °C 2: toluene-4-sulfonic acid / methanol; chloroform / 1.5 h / -15 °C

Multi-step reaction with 2 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 72 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane; methanol / 0.5 h / 0 °C

Reference： [1]Patil, Sucheta V.; Mane, Ramchandra B.; Salunkhe, Manikrao M. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 1, p. 1 - 2]
[2]Janczyk, Matthaeus; Appel, Bettina; Springstubbe, Danilo; Fritz, Hans-Joachim; Mueller, Sabine [Organic and Biomolecular Chemistry, 2012, vol. 10, # 8, p. 1510 - 1513]
[3]Current Patent Assignee: KUMAMOTO UNIVERSITY; YAMASA CORPORATION; NATIONAL CENTER FOR GLOBAL HEALTH AND MEDICINE - JP2017/57200, 2017, A
[4]Baran, Phil S.; Eastgate, Martin D.; Knouse, Kyle W.; Padial, Natalia M.; Rivas-Bascón, Nazaret; Schmidt, Michael A.; Vantourout, Julien C.; Xu, Dongmin; Zheng, Bin [Journal of the American Chemical Society, 2020]

57
[ 961-07-9 ]
[ 68892-41-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: pyridine / 0.5 h / 0 °C 2: pyridine / 2 h 3: aq. NH₄OH / pyridine / 0.5 h 4: 72 percent / DMAP, TEA / pyridine / 1 h
	Multi-step reaction with 3 steps 1: pyridine; methanol / 5 h / 20 °C 2: NaOH / ethanol; H₂O / 0.67 h / 0 - 3 °C 3: 84 percent / 1.) pyridine, 0 deg C, 16 h, 2.) pyridine, CH₃OH, 20 deg C, 1 h
	Multi-step reaction with 2 steps 1: 1.) 1,1,1,3,3,3-hexamethyldisilazane / 1.) DMF, 5 h, 2.) pyridine, 16 h 2: 87 percent / 4-dimethylaminopyridine / pyridine; dioxane / 2 h

	Multi-step reaction with 3 steps 1: 90 percent / pyridine / CHCl₃ / 2 h / Ambient temperature 2: 77 percent / aq. NaOH / ethanol / 0.25 h / 0 °C 3: 85 percent / pyridine / 2 h / Ambient temperature
	Multi-step reaction with 2 steps 1.1: pyridine; chloro-trimethyl-silane / 0.5 h / Cooling with ice 1.2: 2 h / 20 °C 2.1: pyridine; dmap; triethylamine / 4 h / 20 °C
	Multi-step reaction with 2 steps 1.1: pyridine; chloro-trimethyl-silane / 0.5 h / Cooling with ice bath 1.2: 2.5 h / 20 °C 1.3: 0.5 h / Cooling with ice 2.1: pyridine / 5 h / 20 °C

Reference： [1]Awasthi, S. K.; Khanna, V.; Watal, G.; Misra, K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 9, p. 916 - 919]
[2]Denny, William A.; Leupin, Werner; Kearns, David R. [Helvetica Chimica Acta, 1982, vol. 65, # 8, p. 2372 - 2393]
[3]McGee, Danny P. C.; Martin, John C.; Webb, Austin S. [Synthesis, 1983, # 7, p. 540 - 541]
[4]Charubala, R.; Uhlmann, E.; Beiter, A. H.; Pfleiderer, W. [Synthesis, 1984, # 11, p. 965 - 968]
[5]Janczyk, Matthaeus; Appel, Bettina; Springstubbe, Danilo; Fritz, Hans-Joachim; Mueller, Sabine [Organic and Biomolecular Chemistry, 2012, vol. 10, # 8, p. 1510 - 1513]
[6]Current Patent Assignee: HEBREW UNIVERSITY OF JERUSALEM; Yissum Research & Development (in: Hebrew University) - US2011/86813, 2011, A1

58
[ 68892-41-1 ]
[ 119595-55-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Et₃N / acetonitrile 2: acetonitrile
	Multi-step reaction with 2 steps 1: tetrazole / CH₂Cl₂; acetonitrile / 0.25 h / Ambient temperature 2: CH₂Cl₂; acetonitrile / 0.5 h / Ambient temperature

Reference： [1]Brill, Wolfgang K.-D.; Tang, Jin-Yan; Ma, Yun-Xi; Caruthers, Marvin H. [Journal of the American Chemical Society, 1989, vol. 111, # 6, p. 2321 - 2322]
[2]Beaton; Brill; Grandas; Ma; Nielsen; Yau; Caruthers [Tetrahedron, 1991, vol. 47, # 14-15, p. 2377 - 2388]

59
[ 68892-41-1 ]
[ 119595-57-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Et₃N / acetonitrile 2: acetonitrile

Reference： [1]Brill, Wolfgang K.-D.; Tang, Jin-Yan; Ma, Yun-Xi; Caruthers, Marvin H. [Journal of the American Chemical Society, 1989, vol. 111, # 6, p. 2321 - 2322]

60
[ 68892-41-1 ]
[ 119595-58-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Et₃N / acetonitrile 2: acetonitrile

Reference： [1]Brill, Wolfgang K.-D.; Tang, Jin-Yan; Ma, Yun-Xi; Caruthers, Marvin H. [Journal of the American Chemical Society, 1989, vol. 111, # 6, p. 2321 - 2322]

61
[ 68892-41-1 ]
[ 119595-56-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Et₃N / acetonitrile 2: acetonitrile

Reference： [1]Brill, Wolfgang K.-D.; Tang, Jin-Yan; Ma, Yun-Xi; Caruthers, Marvin H. [Journal of the American Chemical Society, 1989, vol. 111, # 6, p. 2321 - 2322]

62
[ 68892-42-2 ]
[ 40615-36-9 ]
N₂-isobutyryl-2',5'-O-bis(4,4'-dimethoxytrityl)-2'-deoxyguanosine [ No CAS ]
[ 68892-41-1 ]

Reference： [1]Patent: EP1253154,2002,A1 .Location in patent: Example 1

63
[ 68892-41-1 ]
[ 102691-36-1 ]
5'-O-dimethoxytrityl-N₂-isobutyryl-2'-deoxyguanosine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With N-ethyl-N,N-diisopropylamine; trifluoroacetic acid In tetrahydrofuran at 20℃; for 12h;	8 Examples 1-11 Examples 1-11; These Examples illustrate the phosphitylation of several protected nucleoside reagents with 2-Cyanoethyl-N,N,N',N'-tetraisopropylphosphordiamidite in the presence of several activators according to the present invention. Eleven phosphitylation reactions (1-11) comprising reacting a protected nucleoside reagent with 2-Cyanoethyl-N,N,N',N'-tetraisopropylphosphordiamidite in the presence of an acid-base activator according to the present invention were conducted, and the product yields of each calculated, as described in the General Procedure, below. The various combinations of protected nucleoside, activator base, activator acid, solvent, and yield for each of the 11 reactions are listed in Table 1. General Procedure: The activator base (1.1 to 1.2 equivalents) is added to the solvent and 0.95 to 1.1 equivalents of activator acid is subsequently added thereto at ambient temperature to form the activator solution. About 1 equivalent of the protected nucleoside is dissolved in about 10 equivalents of the solvent in a separate vessel and about 3 equivalents of the solvent is then distilled off under reduced pressure. About 1 to 1.2 equivalents of 2-Cyanoethyl-N,N,N',N'-tetraisopropylphosphordiamidite is added to the nucleoside mixture at ambient temperature, and the activator solution prepared previously is then added to the nucleoside mixture at ambient temperature with vigorous stirring. After 12 hours, the reaction mixture is diluted with toluene and washed with water. The organic layer is separated, dried over sodium sulfate if necessary, and concentrated under reduced pressure. The yield of the desired amidite is then calculated using HPLC techniques, that is, the resulting product mixture is run through an HPLC column using an appropriate eluent, and the area under the HPLC peaks used to determine the %yield of product in the mixture.
67%	With α-picoline; trifluoroacetic acid In tetrahydrofuran at 20℃; for 12h;	7 Examples 1-11 Examples 1-11; These Examples illustrate the phosphitylation of several protected nucleoside reagents with 2-Cyanoethyl-N,N,N',N'-tetraisopropylphosphordiamidite in the presence of several activators according to the present invention. Eleven phosphitylation reactions (1-11) comprising reacting a protected nucleoside reagent with 2-Cyanoethyl-N,N,N',N'-tetraisopropylphosphordiamidite in the presence of an acid-base activator according to the present invention were conducted, and the product yields of each calculated, as described in the General Procedure, below. The various combinations of protected nucleoside, activator base, activator acid, solvent, and yield for each of the 11 reactions are listed in Table 1. General Procedure: The activator base (1.1 to 1.2 equivalents) is added to the solvent and 0.95 to 1.1 equivalents of activator acid is subsequently added thereto at ambient temperature to form the activator solution. About 1 equivalent of the protected nucleoside is dissolved in about 10 equivalents of the solvent in a separate vessel and about 3 equivalents of the solvent is then distilled off under reduced pressure. About 1 to 1.2 equivalents of 2-Cyanoethyl-N,N,N',N'-tetraisopropylphosphordiamidite is added to the nucleoside mixture at ambient temperature, and the activator solution prepared previously is then added to the nucleoside mixture at ambient temperature with vigorous stirring. After 12 hours, the reaction mixture is diluted with toluene and washed with water. The organic layer is separated, dried over sodium sulfate if necessary, and concentrated under reduced pressure. The yield of the desired amidite is then calculated using HPLC techniques, that is, the resulting product mixture is run through an HPLC column using an appropriate eluent, and the area under the HPLC peaks used to determine the %yield of product in the mixture.

Reference： [1]Current Patent Assignee: HONEYWELL INTERNATIONAL INC - US2003/232980, 2003, A1 Location in patent: Page 6
[2]Current Patent Assignee: HONEYWELL INTERNATIONAL INC - US2003/232980, 2003, A1 Location in patent: Page 6

64
[ 64325-78-6 ]
[ 4546-72-9 ]
[ 68892-41-1 ]

Yield	Reaction Conditions	Operation in experiment
		This compound was prepared from N6 -benzoyl-2'-deoxyadenosine by the same procedure used for the preparation of N2 -isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine.

Reference： [1]Patent: US5672697,1997,A

65
[ 68892-42-2 ]
[ 40615-36-9 ]
[ 68892-41-1 ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine;	N2 -Isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine (2) The tritylation procedure of Jones45 was modified such that no DMAP was used. To 3.37 g (10.0 mmol) of N2 -isobutyryl-2'-deoxyguanosine (that was first concentrated from dry pyridine) in 50 mL of dry pyridine, was added 4.06 g (12.0 mmol, 1.20 equiv.) of 4,4'-dimethoxytrityl chloride. The reaction was stirred for 15 h, and then concentrated. The residue was partitioned between CH2 Cl2 and 0.5% aq. NaHCO3, shaken, and separated. The organic layer was washed with 0.5% aq. NaHCO3 and dried. The crude product was purified by flash chromatography.

Reference： [1]Patent: US5672697,1997,A

66
[ 68892-41-1 ]
[ 124-63-0 ]
[ 1187644-19-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 0℃; for 15.25h; Cooling with ice;	B.3 Step 3-3'-O(R)-(methylsulfonyl)2N-Isobutyryl-5'O-Dimetoxytrityl deoxyguanosine (B5-III)Methanesulfonyl chloride (0.12 mol) was added dropwise over a period of 15 min to a cooled (ice-water-bath) solution of (B5-II) (0.06 mol) in dry pyridine (80 mL). The cooled reactants were then stirred at 0° C. for 15 h. The products were then poured into a vigorously stirred ice water mixture (1500 g). The precipitated solid was collected by filtration, washed with water (4×100 mL) and dried in vacuo over P2O5

Reference： [1]Current Patent Assignee: HEBREW UNIVERSITY OF JERUSALEM; Yissum Research & Development (in: Hebrew University) - US2011/86813, 2011, A1 Location in patent: Page/Page column 34

67
[ 68892-41-1 ]
[ 170236-39-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 5.17 h / 0 - 20 °C / Inert atmosphere 2: sodium tetrahydroborate / dichloromethane; isopropyl alcohol / -60 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: pyridine / 15.25 h / 0 °C / Cooling with ice 2: dimethyl sulfoxide / 90 °C 3: methanol; potassium carbonate / 1 h / 20 °C
	Multi-step reaction with 5 steps 1: sodium carbonate / methanol; dichloromethane / 1 h / 0 °C 2: pyridine / 1 h / 20 °C / Inert atmosphere 3: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere 4: pyridine / 2 h / 20 °C 5: sodium hydroxide / 1,4-dioxane; tetrahydrofuran; methanol / 2 h / 0 °C

Multi-step reaction with 5 steps 1: toluene-4-sulfonic acid / methanol; dichloromethane / 1 h / 0 °C 2: pyridine / 1 h / 20 °C / Inert atmosphere 3: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.75 h / -35 - 0 °C / Inert atmosphere 4: pyridine / 2 h / 20 °C 5: methanol; sodium hydroxide / tetrahydrofuran; 1,4-dioxane / 2 h / 0 °C

Reference： [1]Piperakis, Michael M.; Gaynor, James W.; Fisher, Julie; Cosstick, Richard [Organic and Biomolecular Chemistry, 2013, vol. 11, # 6, p. 966 - 974]
[2]Current Patent Assignee: HEBREW UNIVERSITY OF JERUSALEM; Yissum Research & Development (in: Hebrew University) - US2011/86813, 2011, A1
[3]Current Patent Assignee: IONIS PHARMACEUTICALS - WO2020/72991, 2020, A1
[4]Current Patent Assignee: IONIS PHARMACEUTICALS - WO2021/30763, 2021, A1

68
[ 68892-41-1 ]
[ 109-78-4 ]
[ 160107-22-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5'-O-dimethoxytrityl-N-isobutyryldeoxyguanosine With pyridine; diphenyl hydrogen phosphite for 2h; Inert atmosphere; Stage #2: 3-Hydroxypropionitrile for 2h;	A.1.1 Step 1-2N-Isobutyryl-3'-O-(2-Cyanoethyl)H-Phosphonate-5'O-Dimetoxytrityl deoxyguanosine (A4-I)2N-Isobutyryl-50-Dimetoxytrityl deoxyguanosine (0.5 g, 0.78 mmol) was dried by co-evaporation with dry toluene and suspended in dry pyridine (10 mL) under inert atmosphere. Diphenyl phosphite (250 μL, 1.3 mmol) was added and stirred for 2 h. 3-hydroxypropionitrile (150 μL, 2.16 mmol) was added. After stirring for 2 hr, the solvent was evaporated. The oily crude was used without further purification.

Reference： [1]Current Patent Assignee: HEBREW UNIVERSITY OF JERUSALEM; Yissum Research & Development (in: Hebrew University) - US2011/86813, 2011, A1 Location in patent: Page/Page column 27-28

69
[ 85272-30-6 ]
[ 68892-41-1 ]
[ 152685-42-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-di-tert-butyl-4-methylpyridine In N,N-dimethyl-formamide; acetonitrile at -40℃; for 1h; Inert atmosphere;	4.2. General procedure for preparation of intermediates (taking intermediate T as an example) General procedure: Bis(trifluoromethanesulfony1)diisopropylsilane (2.47 g, 5.99 mmol, 1 equiv) was added via syringe to a solution of 2,6-di-tert-butyl-4-methylpyridine (1.23 g, 5.99 mmol, 1 equiv) in CH3CN (15 mL) in a 200-mL round-bottom flask under N2 atmosphere. The resulted clear solution was cooled to -40 °C, followed by addition of a solution of 5'-O-(4,4'-dimethoxytrityl)thymidine (DMT-T) (3.00 g, 5.51 mmol, 0.92 equiv) and 2,6-di-tert-butyl-4-methylpyridine (295 mg, 1.44 mmol, 0.24 equiv) in DMF (25 mL) dropwise via syringe over 10 min. The reaction mixture was stirred at -40 °C for further 1 h, and the intermediate T was obtained, which was directly used for the next step without purification.refPreviewPlaceHolder8d

Reference： [1]Location in patent: experimental part Lv, Jin-Liang; Zhao, Zhi-Yong; Yang, Zhong-Qiang; Liu, Dong-Sheng; Fan, Qing-Hua [Tetrahedron, 2011, vol. 67, # 47, p. 9080 - 9086]

70
[ 68892-41-1 ]
[ 530-62-1 ]
[ 1357928-20-1 ]

Yield	Reaction Conditions	Operation in experiment
92.7%	In dichloromethane at 20℃; for 4h;	3.2.2.5 (2R,3S,5R)-2-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(2-isobutyramido-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3-yl-1H-imidazole-1-carboxylate (3) 2-Isobutyryl-5′-DMT-2′-deoxyguanosine (10.6g, 16.5mmol) was dissolved in 140mL dry DCM and carbonyldiimidazole (13.4g, 82.5mmol) was added. The mixture was stirred at room temperature for four hours and washed with water. After drying and evaporating the organic phase, the desired compound was obtained as a yellowish foam. No further purification was required. Yield: 11.2g, 92.7% (15.3mmol). (0054) ESI-MS: calc: 733.29. Found [M+H+]: 734.04. (0055) 1H NMR (DMSO-d6): 8.34 (s, 1H, Imidazole), 8.18 (s, 1H, H-8), 7.69 (s, 1H, Imidazole), 7.31 (d, J=7.4Hz, 2H, DMT), 7.18 (d, J=8.4Hz, 8H, DMT), 7.09 (s, 1H, Imidazole), 6.77 (t, J=17.7Hz, 3H, DMT), 6.37 (t, J=14.3Hz, 1H, H-1′), 5.5 (d, J=5.9Hz, 1H, H-3′), 4.45 (m, 1H, H-4′), 3.7 (s, 6H, OCH3), 3.41 (t, J=18Hz, 1H, H-5′), 3.19 (m, 2H, H-5′ and H-2′), 2.84-2.7 (m, 2H, H-2′ and CH (iBu)), 1.1 (d, J=6.74Hz, 6H, CH3 (iBu)).
	In dichloromethane at 20℃; for 4h;	1.A.1 5'-DMT-2-isobutyryl-2'-deoxyguanosine was dissolved in dichloromethane (DCM) and treated with 4 equivalents of carbonyl diimidazole (CDI). After four hours at room temperature, the reaction mix was washed with water, dried and evaporated to afford compound 2.
	With dmap In dichloromethane at 20℃; for 14h;

Reference： [1]Wexselblatt, Ezequiel; Kaspy, Ilana; Glaser, Gad; Katzhendler, Joshua; Yavin, Eylon [European Journal of Medicinal Chemistry, 2013, vol. 70, p. 497 - 504]
[2]Current Patent Assignee: Yissum Research & Development (in: Hebrew University); HEBREW UNIVERSITY OF JERUSALEM - WO2012/17434, 2012, A2 Location in patent: Page/Page column 30
[3]Matsuno, Yuki; Shoji, Takao; Kim, Shokaku; Chiba, Kazuhiro [Organic Letters, 2016, vol. 18, # 4, p. 800 - 803]

71
N,N,N',N'-tetraisopropyl-O-[3-(N,N-dimethylamino)prop-1-yl]phosphordiamidite [ No CAS ]
[ 68892-41-1 ]
N²-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-3'-O-[(N,N-diisopropylamino)(3-[N,N-dimethylamino]prop-1-yl)oxy]phosphinyl-2'-deoxyguanosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-tetrazole In acetonitrile at 25℃; for 10h;	General procedure for the preparation of deoxyribonucleoside phosphoramidites (3a-c) General procedure: To a stirred solution of 1 (401 mg, 1.20 mmol) in MeCN (20 ml) was added the appropriately protected deoxyribonucleoside (2a-c, 1.0 mmol) along with 0.45 M 1H-tetrazole in MeCN (2.2 ml, 1.0 mmol). The reaction mixture was stirred for 3 h (2a-b) or 10 h (2c) at ~25 C. The reaction mixture was then concentrated under reduced pressure to a gummy material; the crude phosphoramidite was purified by chromatography on silica gel (~25 g), which was equilibrated in a solution of hexane:Et3N (95:5 v/v). The product was eluted from the column using a gradient of CH2Cl2 (0 → 95%) in hexane: Et3N (95:5 v/v). Fractions containing the pure phosphoramidite, as indicated by TLC, were pooled together and were evaporated to dryness under low pressure. The foamy material was dissolved in dry benzene (5 ml) and the resulting solution was manually stirred in a dry ice-acetone bath. The frozen material was then lyophilized under high vacuum to give the phosphoramidite 3a-c, as a white powder, the yield of which was in the range of 62-75%.

Reference： [1]Jain, Harsh V.; Takeda, Kazuyo; Tami, Cecilia; Verthelyi, Daniela; Beaucage, Serge L. [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 20, p. 6224 - 6232]

72
[ 80817-46-5 ]
[ 68892-41-1 ]
C₄₇H₄₄ClN₈O₁₀P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In 1,4-dioxane
	With pyridine In 1,4-dioxane at 20℃; for 3h;	General procedure: Thecouplings were carried out essentially as described previously[8]. A solution of 2-chlorophenyl phosphorodichloridate(7.6 mmol, 1.88 g) in anhydrous dioxane (5.75 mL) was addedin one portion to a suspension of 1-hydroxybenzotriazole(15.2 mmol, 2.06 g; dried in vacuo over P2O5 at 55 °C for 3 d)and pyridine (15 mmol, 1.2 mL) in anhydrous dioxane (30 mL).The reaction mixture was stirred for 2 h, and the precipitate wasfiltered off under anhydrous conditions to give a stock solutionof bis(benzotriazol-1-yl) 2-chlorophenyl phosphate(0.2 mol L-1) as a clear colorless liquid. The solution(ρ = 1.057 g L-1) could be stored for several weeks at -20 °C.
	With pyridine In 1,4-dioxane

Reference： [1]Kungurtsev, Vyacheslav; Virta, Pasi; Loennberg, Harri [European Journal of Organic Chemistry, 2013, # 35, p. 7886 - 7890]
[2]Jabgunde, Amit M.; Molina, Alejandro Gimenez; Virta, Pasi; Lönnberg, Harri; Flitsch [Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 1553 - 1560]
[3]Kungurtsev; Lönnberg; Virta [RSC Advances, 2016, vol. 6, # 107, p. 105428 - 105432]

73
[ 68892-41-1 ]
[ 108-24-7 ]
5'-(4,4'-dimethoxytrityl)-2'-deoxy-N2-acetyl-N2,N6-diaminopurine riboside [ No CAS ]
[ 161786-58-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5'-O-dimethoxytrityl-N-isobutyryldeoxyguanosine; acetic anhydride With pyridine; 1-methyl-1H-imidazole In toluene at 20℃; for 96h; Stage #2: With ammonium hydroxide In methanol at 55℃; for 16h;	5′-(4,4′-dimethoxytrityl)-2′-deoxy-N²-acetyl-N²,N⁶-diaminopurine riboside (5a) To 5′-(2,2′-dimethoxytrityl)-2′-deoxy-N2-isobutyryl guanosine (3a, 6.40 g, 10 mmol) in a 1 L bottle was added 400 mL of a 2:3:5 v/v/v solution ofN-methylimidazole, pyridine, toluene. The bottle was capped, and the solution was mixed until homogeneous. A 1:4 v/v solution of acetic anhydride and toluene (400 mL) was added. The bottle was capped, and the solution was mixed thoroughly. The solution sat at room temperature for 4 days. The solution was diluted with 500 mL of ethyl acetate and washed twice with 600 mL portions of saturated aqueous sodium bicarbonate solution. The organic layer was dried with sodium sulfate, filtered, and concentrated under vacuum to ~10 mL of a heterogeneous brown mixture. MeOH (40 mL) was added to dissolve the residue. Concentrated ammonium hydroxide (30% w/w, 400 mL) was added. The solution was mixed and transferred to a 500 mL Pyrex media bottle. The bottle was capped and heated to 55 °C for 16 h. The solution was cooled to room temperature. The crude mixture was analyzed by RP-HPLC-MS, and it was determined to contain 8% of compound 5a by UV quantification. A portion of the crude was purified by the chromatography procedure written below to yield a white solid:1H NMR (300MHz, DMSO-d6) δ 9.86 (s, 1H), 8.21 (s, 1H), 7.46 - 7.37 (m, 2H), 7.37 - 7.21 (m, 11H), 6.88 (t,J=9.1 Hz, 5H), 6.37 (t,J=6.5 Hz, 1H), 5.41 (d,J=4.5 Hz, 1H), 4.60 - 4.50 (m, 1H), 4.08 - 3.98 (m, 1H), 3.81 (d,J=1.0 Hz, 8H), 3.59 (s, 2H), 3.37 - 3.25 (m, 1H), 3.24 - 3.14 (m, 1H), 2.91 (quin,J=6.4 Hz, 1H), 2.47 - 2.33 (m, 1H), 2.25 (s, 3H);13C NMR 125MHz, DMSO-d6) δ 169.1, 157.9, 156.0, 152.8, 149.9, 144.8, 138.4, 135.6, 135.5, 129.6, 127.6, 126.5, 116.1, 113.0, 85.8, 85.4, 82.9, 70.6, 69.7, 64.2, 54.9, 24.4. HRMSm/zcalculated for C33H34N6O6[M - H]-609.2467, found 609.2472

Reference： [1]Rodriguez, Andrew A.; Cedillo, Isaiah; Mowery, Brendan P.; Gaus, Hans J.; Krishnamoorthy, Seetha S.; McPherson, Andrew K. [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3243 - 3246]

74
N,N,N',N'-tetraisopropyl-[1-(2-nitrophenyl) ethyl]phosphorodiamidite [ No CAS ]
[ 68892-41-1 ]
5'-O-(4,4'-dimethoxytrityl)-N²-isobutyrylguanosine-3'-{O-[1-(2-nitrophenyl)ethyl]-N,N'-diisopropyl-amino}phosphoramidite [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With 1H-tetrazole; bis(diisopropylamino)chlorophosphine In dichloromethane at 20℃; for 4h;

Reference： [1]Wu, Li; Pei, Fen; Zhang, Jinhao; Wu, Junzhou; Feng, Mengke; Wang, Yuan; Jin, Hongwei; Zhang, Liangren; Tang, Xinjing [Chemistry - A European Journal, 2014, vol. 20, # 38, p. 12114 - 12122]

75
[ 68892-42-2 ]
C₂₃H₁₉F₃O₄ [ No CAS ]
[ 68892-41-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃; for 2h;Inert atmosphere; Schlenk technique;	General procedure: To a solution of trityl alcohol (0.6 mmol, 1.2 equiv.) in dry CH2Cl2 (5 mL) in a round-bottomed flask was added trifluoroacetic anhydride (0.21 mL, 1.5 mmol, 3 equiv.) at rt under argon from a Schlenk line. A deep red solution was formed immediately (with 1a, the color was slightly lighter). After stirring for 2 h, the mixture was concentrated to dryness on a rotary evaporator under reduced pressure provided by a water aspirator. The flask was reattached to the Schlenk line and flushed with argon. The intermediate trityl cation was re-dissolved in dry THF (5 mL), and added via a cannula to a solution of alcohol substrate (0.5 mmol, 1 equiv.) and DIEA (0.175 mL, 1 mmol, 2 equiv.) in dry THF (5 mL) at rt (5-8) or 0 C (3, 9-11). After stirring for 2 h (while warming to rt slowly if applicable), the reaction mixture was poured into a separatory funnel containing 5% NaHCO3 (15 mL), and extracted with EtOAc (10 mL×2). The extracts were dried over anhydrous Na2SO4, filtered, and concentrated.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 3877 - 3880

76
[ 1528733-82-5 ]
[ 68892-41-1 ]
C₅₄H₅₉N₆O₈PSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With chloro-trimethyl-silane; triethylamine In tetrahydrofuran at 20℃; Cooling;	General procedure: The nucleoside 109-112 (178.5 mmol) was dried in a single neck 2000 mL round bottom flask by azeotropic evaporation by anhydrous toluene (250 mL) and dried under vacuum for 18 h. This dried compound was dissolved in dry THF (375 ~ 600 mL) and transferred into three neck 2000 mL round bottom flask with magnetic stir bar. Then, triethylamine (125 mL, 898 mmol), dried over CaH2, was added into the reaction mixture, then cooled to -10 ~ -20 °C. Chlorotrimethylsilane (22.6 mL, 179 mmol) was added dropwise over 10 min. A THF solution (215 mL) of the crude chlorooxazaphospholidine (253 mmol) was added through cannula over ~ 15 min then, gradually warmed to room temperature about 1 h. LCMS showed that the starting material was consumed. Then, the reaction mixture was treated with water (2.4 mL, 0.13 mol) and the reaction mixture was further stirred less than 5 min then, 25 g of MgS04 was added followed by stirring the reaction mixture for another 10 min. Then, it was filtered carefully under vacuum/argon and the resulting filtrate was reduced to yellow foam by rotary evaporation then dried under high vacuum overnight. Crude mixture was purified by silica column (which was pre-deactivated with acetonitrile) chromatography using ethyl acetate (5% TEA) and acetonitrile (5% TEA) as eluents.

Reference： [1]Current Patent Assignee: WAVE LIFE SCIENCES LTD. - WO2018/98264, 2018, A1 Location in patent: Paragraph 00229; 00230

77
N,N,N’,N’-tetraisopropyl-1-(3-methoxypropyl)phosphanediamine [ No CAS ]
[ 68892-41-1 ]
5'-O-(4,4'-dimethoxytrityl)-3'-O-[3-methoxypropyl(diisopropylamino)phosphanyl]-2'-deoxy-(2-N-isobutyryl)guanosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With 1-methyl-1H-imidazole; 1H-tetrazole In N,N-dimethyl-formamide at 20℃; Inert atmosphere;

Reference： [1]Migawa, Michael T.; Shen, Wen; Brad Wan; Vasquez, Guillermo; Oestergaard, Michael E.; Low, Audrey; De Hoyos, Cheryl L.; Gupta, Ruchi; Murray, Susan; Tanowitz, Michael; Bell, Melanie; Nichols, Joshua G.; Gaus, Hans; Xue-Hai, Liang; Swayze, Eric E.; Crooke, Stanley T.; Seth, Punit P. [Nucleic Acids Research, 2019, vol. 47, # 11, p. 5465 - 5479]

78
(2R,3aR,6S,7aR)-3a-methyl-2-((perfluorophenyl)thio)-6-(prop-1-en-2-yl)hexahydrobenzo[d][1,3,2]oxathiaphosphole 2-sulfide [ No CAS ]
[ 68892-41-1 ]
N-(9-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-(((2S,3aR,6S,7aR)-3a-methyl-6-(prop-1-en-2-yl)-2-sulfidohexahydrobenzo[d][1,3,2]oxathiaphosphol-2-yl)oxy)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47.1%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 0 - 20℃; for 0.166667h; Inert atmosphere;	16.2.19 2.19. Compound 3-130 A dry 250 mL round bottom flask was charged with (2R,3aR,6S,7aR)-3a-methyl- (1119) 2-((perfluorophenyl)thio)-6-(prop-1-en-2-yl)hexahydrobenzo[d][ 1,3,2]oxathiaphosphole 2-sulfide(5.8 g, 12.99 mmol) and N-(9-((2R,4S,5R)-5-((bis(4- methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-lH-purin-2-yl)isobutyramide (8.9g, l3.9mmol) under a stream of nitrogen. N,N-dimethylformamide (50 mL) was added to the mixture which was allowed to stir at room temperature until it became homogeneous. The mixture was cooled to 0 °C. 1,8-diazabicyclo[5.4.0]undec-7-ene (2.081 mL, 13.91 mmol) was then added to the mixture drop-wise. The mixture was stirred at 0 °C for 10 minutes. (1120) [0343] The cold reaction mixture was diluted with ~200mL toluene. The mixture was transferred to a separatory funnel where it was washed twice with 1M pH 7.4 phosphate buffer solution (Aldrich P3619). Organics were dried with Na2S04. The mixture was filtered and the filtrate was concentrated to dryness. 9.25g. Evaporate onto celite (toluene) The mixture was purified via Biotage medium pressure liquid chromatography (Silica; Isco RediSep l20g; 70% EtOAc-Hex 1% triethylamine to 100% Ethyl acetate 1% triethylamine over 6 CV, hold at 100% for 10CV). Major peak was isolated. N-(9- ((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-(((2S,3aR,6S,7aR)- 3a-methyl-6-(prop-l-en-2-yl)-2-sulfidohexahydrobenzo[d][l,3,2]oxathiaphosphol-2-yl)oxy)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-lH-purin-2-yl)isobutyramide (5.8g, 6.55 mmol, 47.1 % yield). . 1H NMR (500 MHz, ACETONITRILE-d3) d 12.06 - 11.78 (m, 1H), 9.22 (br s, 1H), 7.82 (s, 1H), 7.46 - 7.34 (m, 2H), 7.34- 7.16 (m, 8H), 6.90 - 6.72 (m, 4H), 6.26 (t, =6.8 Hz, 1H),5.54-5.42 (m, 1H), 4.99 (d, =l .2 Hz, 1H), 4.87 (s, 1H), 4.43 (dt, =l2.7, 3.2 Hz, 1H), 4.30 (dt, J=5.8, 3.1 Hz, 1H), 4.09 (q, J=1.1 Hz, 1H), 3.76 (d, J=2.9 Hz, 6H), 3.45 (dd, =l0.5,5.9 Hz, 1H), 3.29 (dd, =l0.4, 3.5 Hz, 1H), 3.15- 3.02 (m, 1H), 2.70 - 2.53 (m, 3H), 2.20 (s, 8H), 2.03- 1.91 (m, 7H), 1.76 (s, 3H), 1.67 (s, 3H), 1.17 (t, J=7.2 Hz, 6H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; SCRIPPS RESEARCH - WO2019/200273, 2019, A1 Location in patent: Paragraph 0313; 0342-0343

79
[ 4712-55-4 ]
[ 68892-41-1 ]
bicarbonate salt of 1,8-diazabicyclo[5.4.0]undec-7-ene [ No CAS ]
1,8-diazabicyclo[5.4.0]undec-7-enium 5′-O-dimethoxytrityl-N²-isobutyryldeoxyguanosine 3′-H-phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: diphenyl hydrogen phosphite; 5'-O-dimethoxytrityl-N-isobutyryldeoxyguanosine With pyridine In water at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: With triethylamine In water at 20℃; for 1h; Inert atmosphere; Stage #3: bicarbonate salt of 1,8-diazabicyclo[5.4.0]undec-7-ene With pyridine In chloroform; water Inert atmosphere;

Reference： [1]Sato, Kazuki; Imai, Hiroki; Shuto, Tomohito; Hara, Rintaro Iwata; Wada, Takeshi [Journal of Organic Chemistry, 2019, vol. 84, # 23, p. 15032 - 15041]

80
[ 68892-41-1 ]
C₅₂H₆₆N₇O₁₃PSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 72 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane; methanol / 0.5 h / 0 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / N,N-dimethyl-formamide / 16 h / 25 °C / Inert atmosphere; Sealed tube

Reference： [1]Baran, Phil S.; Eastgate, Martin D.; Knouse, Kyle W.; Padial, Natalia M.; Rivas-Bascón, Nazaret; Schmidt, Michael A.; Vantourout, Julien C.; Xu, Dongmin; Zheng, Bin [Journal of the American Chemical Society, 2020]

81
[ 68892-41-1 ]
C₅₉H₆₉N₁₀O₁₂PSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 72 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane; methanol / 0.5 h / 0 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / N,N-dimethyl-formamide / 16 h / 25 °C / Inert atmosphere; Sealed tube

Reference： [1]Baran, Phil S.; Eastgate, Martin D.; Knouse, Kyle W.; Padial, Natalia M.; Rivas-Bascón, Nazaret; Schmidt, Michael A.; Vantourout, Julien C.; Xu, Dongmin; Zheng, Bin [Journal of the American Chemical Society, 2020]

82
[ 68892-41-1 ]
C₅₈H₆₉N₈O₁₃PSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 72 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane; methanol / 0.5 h / 0 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / N,N-dimethyl-formamide / 16 h / 25 °C / Inert atmosphere; Sealed tube

Reference： [1]Baran, Phil S.; Eastgate, Martin D.; Knouse, Kyle W.; Padial, Natalia M.; Rivas-Bascón, Nazaret; Schmidt, Michael A.; Vantourout, Julien C.; Xu, Dongmin; Zheng, Bin [Journal of the American Chemical Society, 2020]

83
[ 68892-41-1 ]
C₅₆H₇₁N₁₀O₁₃PSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 72 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane; methanol / 0.5 h / 0 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / N,N-dimethyl-formamide / 16 h / 25 °C / Inert atmosphere; Sealed tube

Reference： [1]Baran, Phil S.; Eastgate, Martin D.; Knouse, Kyle W.; Padial, Natalia M.; Rivas-Bascón, Nazaret; Schmidt, Michael A.; Vantourout, Julien C.; Xu, Dongmin; Zheng, Bin [Journal of the American Chemical Society, 2020]

84
[ 68892-41-1 ]
C₅₈H₆₉N₈O₁₃PSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 72 h / 0 - 20 °C 2: toluene-4-sulfonic acid / dichloromethane; methanol / 0.5 h / 0 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / N,N-dimethyl-formamide / 16 h / 25 °C / Inert atmosphere; Sealed tube

Reference： [1]Baran, Phil S.; Eastgate, Martin D.; Knouse, Kyle W.; Padial, Natalia M.; Rivas-Bascón, Nazaret; Schmidt, Michael A.; Vantourout, Julien C.; Xu, Dongmin; Zheng, Bin [Journal of the American Chemical Society, 2020]

85
[ 68892-41-1 ]
C₁₁H₁₉OPS₂ [ No CAS ]
[ 74-88-4 ]
(S)-Methyl-phosphonothioic acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester S-methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	Stage #1: 5'-O-dimethoxytrityl-N-isobutyryldeoxyguanosine; C₁₁H₁₉OPS₂ With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Stage #2: methyl iodide With triethylamine In tetrahydrofuran at 20℃; for 1h; stereospecific reaction;

Reference： [1]Baran, Phil S.; Eastgate, Martin D.; Knouse, Kyle W.; Padial, Natalia M.; Rivas-Bascón, Nazaret; Schmidt, Michael A.; Vantourout, Julien C.; Xu, Dongmin; Zheng, Bin [Journal of the American Chemical Society, 2020]

86
[ 68892-41-1 ]
C₁₁H₁₉OPS₂ [ No CAS ]
[ 74-88-4 ]
(R)-Methyl-phosphonothioic acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester S-methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: 5'-O-dimethoxytrityl-N-isobutyryldeoxyguanosine; C₁₁H₁₉OPS₂ With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Stage #2: methyl iodide With triethylamine In tetrahydrofuran at 20℃; for 1h; stereospecific reaction;

Reference： [1]Baran, Phil S.; Eastgate, Martin D.; Knouse, Kyle W.; Padial, Natalia M.; Rivas-Bascón, Nazaret; Schmidt, Michael A.; Vantourout, Julien C.; Xu, Dongmin; Zheng, Bin [Journal of the American Chemical Society, 2020]

87
[ 68892-41-1 ]
C₇₅H₁₀₀N₁₉O₃₀P₅S₄ [ No CAS ]
C₁₀₄H₁₂₂N₂₃O₃₇P₅S₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: 5'-O-dimethoxytrityl-N-isobutyryldeoxyguanosine; C₇₅H₁₀₀N₁₉O₃₀P₅S₄ With 4,5-dicyano-1H-imidazole In acetonitrile Stage #2: With 3-((N,N-dimethylaminomethylidene)amino)-3H-1,2,4-dithiazole In acetonitrile Stage #3: With 1H-imidazole; pyridine hydrogenfluoride In tetrahydrofuran at 0℃; for 2h;	2.2 General procedure for preparation of 5' DMT-MOE CCGU-OH General procedure: Compound 4-8 (153 g, 92.8 mmol) and compound 4-6 (89.9 g, 97.5 mmol) were co- evaporated with ACN (400 mL x 3) under Ar2 in a 3000 mL single-necked round bottle, and 3A molecular sieve (45.0 g) were added to the single-necked bottle, under Ar2 pressure ACN (928 mL) was added. The mixture was stirred at 25oC for an hour, and then Py-TFA (1 M, 139 mL) was added to the mixture. HPLC showed the starting material was consumed completely. [0406] After the coupling reaction finished DDTT (20.0 g, 97.5 mmol) was added to the mixture. The reaction mixture was stirred at 25oC for 0.5 hr and changed from yellow cloudy to yellow homogenous solution which suggested the reaction went to completion and then cooled down to 0oC in ice bath for 30 min.At the same time, a 500 mL round bottom flask was charged with imidazole (127 g, 1.87 mol ) and anhydrous THF (232 mL) and placed in the ice bath for 30 min. The HF-Py (24.3 mL, 70.0% purity) was slowly added and then stirred for another 15 min (A homogeneous solution was obtained from this step). The solution from the last step was slowly added to the reaction mixture from the last reaction mixture by the peristaltic pump (1 mL/5min dropping rate) and stirred for 1-2 hours at 0oC. The completion of reaction can be monitored by HPLC. HPLC showed the starting material was consumed completely. The mixture was diluted with EA (4500 mL) and slowly neutralized by NaHCO3/H2O (2500 mL) at 0oC. The organic layer was separated and washed with NaHCO3/H2O (2500 mL), brine (2000 mL). The organic layer was dried and concentrated to dryness. The crude was re- dissolved in DCM (600 mL). The crude solvent was slowly dropped to a solvent of tBuOMe (6000 mL). Desired product was precipitated out. The product was collected as a light- yellow solid after filtration, and the solid cake was washed with tBuOMe (600 mL x2). 4-9 (5' DMT-MOE CCGU-OH) (190 g, 90.5% yield, 94.8% purity) was obtained as a light yellow solid. HPLC-MS for MOE-CCGU 4mer (4-9) is shown in FIG. 4.HPLC-MS method for compound 4-9: • Column: ACQUITY UPLC BEH Shield RP18 Column, 130Å, 1.7 µm, 2.1 mm X 150 mm; • Column temperature: 60°C; • MS analysis was done on the Thermo Orbitrap Fusion with 60k resolution and mass range from 400 to 2000; • MS polarity: positive • Mobile phase A: 20 mM Ammonium Acetate in ACN:Water=25:75; Mobile phase B: acetonitrile; • Gradient:

Reference： [1]Current Patent Assignee: BIOGEN IDEC INC.; AJINOMOTO COMPANY INC - WO2020/227618, 2020, A2 Location in patent: Paragraph 0405-0408; 0443

88
[ 51747-24-1 ]
[ 68892-41-1 ]
[ 115131-08-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: N,N-diisopropylamino methylphosphonamidic chloride With N-ethyl-N,N-diisopropylamine In dichloromethane; toluene for 0.0833333h; Stage #2: N₂-Isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine With 9-azajulolidine In dichloromethane; toluene for 0.166667h;	4 General procedure: i) An activated resin obtained in Example 8 (AM-PS-Het5, 250 mg) was loaded into an HPLC column of stainless steel (75 mm x 4.6 mm). The resulting column packed with the activated resin was flushed with toluene at a flow rate of 1.00 mL/min for 15 minutes. The column was weighed (mToiuene + resin + column = 43.118 g), flushed with dichloromethane (DCM) with a flow rate of (0151) 1.00 mL/min for 15 minutes, and then weighted again (rriDCM + res n + column = 43.588 g). The void volume, Vvoid, of the system was determined to establish a connection between flow rate and estimated residence time of the liquid passing through the column. The void volume of the column was calculated using the formula: (0152) Am solvent switch 43.5588 g - 43.118 g (0153) ^void = 1.00 raL (0154) 1 3 0 867 wherein, Arrisoivent switch is the difference in mass and Apsoivent the difference in density when switching solvents, ii) a loaded resin was prepared by loading the activated resin 4 times with PCI (0.10 M) and L/,/V-diisopropylethylamine (DIPEA, 0.10 M) in DCM (2 mL) with flow rate of 1.00 mL/min for 5 minutes including DCM wash, iii) the substrate alcohol (0.10 M, 0.114 mmol) and DMAP (0.15 M, 0.171 mmol) or another base, such as PPY or 9AJ, were dissolved in DCM (1 mL) and eluted through the loaded resin with a flow rate of between 0.125 mL/min and 1.00 mL/min (residence time between 8 minutes and 1 minute), iV) fractions comprising the synthesized phosphoramidites were collected for 2.5 times the residence time.
92%	Stage #1: N,N-diisopropylamino methylphosphonamidic chloride With N-ethyl-N,N-diisopropylamine In dichloromethane; toluene for 0.0833333h; Stage #2: N₂-Isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine With 9-azajulolidine In dichloromethane; toluene for 0.166667h;	4 General procedure: i) An activated resin obtained in Example 8 (AM-PS-Het5, 250 mg) was loaded into an HPLC column of stainless steel (75 mm x 4.6 mm). The resulting column packed with the activated resin was flushed with toluene at a flow rate of 1.00 mL/min for 15 minutes. The column was weighed (mToiuene + resin + column = 43.118 g), flushed with dichloromethane (DCM) with a flow rate of (0151) 1.00 mL/min for 15 minutes, and then weighted again (rriDCM + res n + column = 43.588 g). The void volume, Vvoid, of the system was determined to establish a connection between flow rate and estimated residence time of the liquid passing through the column. The void volume of the column was calculated using the formula: (0152) Am solvent switch 43.5588 g - 43.118 g (0153) ^void = 1.00 raL (0154) 1 3 0 867 wherein, Arrisoivent switch is the difference in mass and Apsoivent the difference in density when switching solvents, ii) a loaded resin was prepared by loading the activated resin 4 times with PCI (0.10 M) and L/,/V-diisopropylethylamine (DIPEA, 0.10 M) in DCM (2 mL) with flow rate of 1.00 mL/min for 5 minutes including DCM wash, iii) the substrate alcohol (0.10 M, 0.114 mmol) and DMAP (0.15 M, 0.171 mmol) or another base, such as PPY or 9AJ, were dissolved in DCM (1 mL) and eluted through the loaded resin with a flow rate of between 0.125 mL/min and 1.00 mL/min (residence time between 8 minutes and 1 minute), iV) fractions comprising the synthesized phosphoramidites were collected for 2.5 times the residence time.

Reference： [1]Current Patent Assignee: AARHUS UNIVERSITY - WO2022/13393, 2022, A1 Location in patent: Page/Page column 36-38
[2]Current Patent Assignee: AARHUS UNIVERSITY - WO2022/13393, 2022, A1 Location in patent: Page/Page column 36-38

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	68892-41-1	MDL No. :	MFCD00010059
Formula :	C₃₅H₃₇N₅O₇	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RMQXDNUKLIDXOS-ZGIBFIJWSA-N
M.W :	639.70	Pubchem ID :	135445746
Synonyms :	5'-O-DMT-N2-ibu-dG;N2-Isobutyryl-5′-O-(4,4′-dimethoxytrityl)-2′-deoxyguanosine;iBu-DMT-dG;5'-O-DMT-N2-Isobutyryl-2'-Deoxyguanosine	Chemical Name :	N2-Isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine

Num. heavy atoms :	47
Num. arom. heavy atoms :	27
Fraction Csp3 :	0.31
Num. rotatable bonds :	12
Num. H-bond acceptors :	9.0
Num. H-bond donors :	3.0
Molar Refractivity :	174.92
TPSA :	149.82 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-7.17 cm/s

Log Po/w (iLOGP) :	3.59
Log Po/w (XLOGP3) :	4.27
Log Po/w (WLOGP) :	3.76
Log Po/w (MLOGP) :	1.08
Log Po/w (SILICOS-IT) :	4.2
Consensus Log Po/w :	3.38

[ CAS No. 68892-41-1 ] {[proInfo.proName]}

Quality Control of [ 68892-41-1 ]

Related Doc. of [ 68892-41-1 ]

Product Details of [ 68892-41-1 ]

Calculated chemistry of [ 68892-41-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 68892-41-1 ]

Application In Synthesis of [ 68892-41-1 ]

[ 68892-41-1 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	2.0
Ghose :	None
Veber :	2.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.17

Log S (ESOL) :	-6.13
Solubility :	0.000475 mg/ml ; 0.000000742 mol/l
Class :	Poorly soluble
Log S (Ali) :	-7.13
Solubility :	0.0000476 mg/ml ; 0.0000000744 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-9.3
Solubility :	0.000000322 mg/ml ; 0.0000000005 mol/l
Class :	Poorly soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	5.77

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

Precautionary Statements-General
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Prevention
Code	Phrase
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P222	Do not allow contact with air.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
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Response
Code	Phrase
P301	IF SWALLOWED:
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P320
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P321
P322
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P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
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.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
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P411
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P413
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P422
P402 + P404	Store in a dry place. Store in a closed container.
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P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling