[ CAS No. 951-77-9 ] {[proInfo.proName]}

Name: 951-77-9|4-Amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one|97%
Brand: Ambeed
SKU: A106243
Price: 5.0 USD
Availability: InStock
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Quality Control of [ 951-77-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 951-77-9 ]

Product Details of [ 951-77-9 ]

CAS No. :	951-77-9	MDL No. :
Formula :	C₉H₁₃N₃O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CKTSBUTUHBMZGZ-SHYZEUOFSA-N
M.W :	227.22	Pubchem ID :	13711
Synonyms :	Deoxycytidine;Cytosine deoxyriboside;dC;Deoxyribose cytidine

Calculated chemistry of [ 951-77-9 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.56
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	3.0
Molar Refractivity :	54.69
TPSA :	110.6 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.83
Log Po/w (XLOGP3) :	-1.77
Log Po/w (WLOGP) :	-1.85
Log Po/w (MLOGP) :	-1.5
Log Po/w (SILICOS-IT) :	-1.37
Consensus Log Po/w :	-1.13

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.28
Solubility :	119.0 mg/ml ; 0.526 mol/l
Class :	Very soluble
Log S (Ali) :	-0.04
Solubility :	209.0 mg/ml ; 0.918 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.2
Solubility :	363.0 mg/ml ; 1.6 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.53

Safety of [ 951-77-9 ]

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

Application In Synthesis of [ 951-77-9 ]

* 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.

Upstream synthesis route of [ 951-77-9 ]
Downstream synthetic route of [ 951-77-9 ]

[ 951-77-9 ] Synthesis Path-Upstream 1~12

1
[ 3226-65-1 ]
[ 951-77-9 ]
[ 838-07-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 260 - 265

2
[ 67-68-5 ]
[ 951-77-9 ]
[ 838-07-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 260 - 265

3
[ 951-77-9 ]
[ 1022-79-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium azide; bromoisocyanuric acid monosodium salt In water; acetonitrile at 20℃; for 0.5 h;	General procedure: 2'-O-Methyluridine (5, 0.103 g, 0.4 mmol) was dissolved in aqueous acetonitrile solution(H2O:CH3CN 1:9, 5 mL) under stirring. NaN3 (0.104 g, 1.6 mmol) was added, followed by addition of SMBI (0.101 g, 0.44 mmol) at r.t. and the mixture was stirred. Progress of the reaction was followedby TLC. On completion of the reaction after 1.5 h, the reaction mixture was filtered, evaporated todryness under reduced pressure and coevaporated with acetonitrile (2 × 2 mL). The crude reactionmixture was purified by column chromatography (4percent–6percent MeOH in DCM, v/v) to afford bromonucleoside 6 (0.117 g, 93percent) in pure form as a white solid

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 5, p. 1007 - 1013
[2] Synthesis, 2009, # 23, p. 3957 - 3962
[3] European Journal of Organic Chemistry, 2010, # 24, p. 4713 - 4718
[4] Molecules, 2013, vol. 18, # 10, p. 12740 - 12750
[5] Journal of the American Chemical Society, 1959, vol. 81, p. 1756
[6] Chemical Research in Toxicology, 1996, vol. 9, # 7, p. 1145 - 1151
[7] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 9, p. 5164 - 5170

4
[ 951-77-9 ]
[ 1022-79-3 ]
[ 52278-77-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 9, p. 5164 - 5170

5
[ 951-77-9 ]
[ 34371-14-7 ]

Reference： [1] Journal of the American Chemical Society, 1999, vol. 121, # 17, p. 4101 - 4110

6
[ 951-77-9 ]
[ 611-53-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With iodine; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl-formamide at 20℃; for 2 h;	dC 1 In a flame dried round bottom flask 10.0 g dC (44.0 mmol, 1.0 eq), 7.70 g iodine (26.4 mmol, 0.6 eq) and 1 1.4 g mCPBA (70 percent, 46.2 mmol, 1 .05 eq) were dissolved in 120 mL DMF. The reaction mixture was stirred 2 h at room temperature and subsequently evaporated to dryness, (small amounts of DMF are tolerable during subsequent column chromatography) Purification by column chromatography (DCM/MeOH/H₂0/NH₃ 190:10:0.6:0.6 --> 90:10:0.6:0.6) yielded 9.71 g (63 percent) of 1 as an orange solid. ¹H NMR (400 MHz, CDCI₃/MeOD) δ (ppm) = 8.46 (s, 1 H), 6.13 (t, ³J=6.0, 1 H), 4.34 (dt, ³J=4.7, ³J=6.3 , 1 H), 3.93 (dt, ³J=3.0, ³J=4.3, 1 H), 3.84 (dd, ³J=3.0 Hz, ²J=12.1 , 1 H), 3.72 (dd, ³ =3.2, ²J=12.1 , 1 H), 2.39 (ddd, ³J=4.8, ³J=6.3, ²J=13.7, 1 H), 2.20 - 2.09 (m, 1 H). ¹³C NMR (101 MHz, MeOD) δ (ppm) = 163.9, 153.9, 150.9, 89.5, 88.3, 71 .5, 62.2, 56.2, 42.5. HRMS (ESI +) calculated for C₉H₁₃IN₃0₄⁺ [M+H]⁺: 353.9945, found: 353.9944. melting range: 133°C - 135 °C (decomposition) IR (ATR): 3191 (w), 1718 (m), 1642 (s), 1286 (m), 1087 (s), 957 (s), 750 (m).
63%	With iodine; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl-formamide at 20℃; for 2 h; Inert atmosphere	5-(Iodo)deoxycytidine (1) In a flame dried round bottom flask 10.0 g dC (44.0 mmol, 1.0 eq), 7.70 g iodine (26.4 mmol, 0.6 eq) and 11.4 g mCPBA (70percent, 46.2 mmol, 1.05 eq) were dissolved in 120 mL DMF. The reaction mixture was stirred 2 h at room temperature and subsequently evaporated to dryness. (small amounts of DMF are tolerable during subsequent column chromatography) Purification by column chromatography (DCM/MeOH/H₂O/NH₃ 190:10:0.6:0.6→90:10:0.6:0.6) yielded 9.71 g (63percent) of 1 as an orange solid. ¹H NMR (400 MHz, CDCl₃/MeOD) δ (ppm)=8.46 (s, 1H), 6.13 (t, ³J=6.0, 1H), 4.34 (dt, ³J=4.7, ³J=6.3, 1H), 3.93 (dt, ³J=3.0, ³J=4.3, 1H), 3.84 (dd, ³J=3.0 Hz, ²J=12.1, 1H), 3.72 (dd, ³J=3.2, ²J=12.1, 1H), 2.39 (ddd, ³J=4.8, ³J=6.3, ²J=13.7, 1H), 2.20-2.09 (m, 1H). ¹³C NMR (101 MHz, MeOD) δ (ppm)=163.9, 153.9, 150.9, 89.5, 88.3, 71.5, 62.2, 56.2, 42.5. HRMS (ESI+) calculated for C₉H₁₃IN₃O₄⁺[M+H]⁺: 353.9945, found: 353.9944. melting range: 133° C.-135° C. (decomposition) IR (ATR): 3191 (w), 1718 (m), 1642 (s), 1286 (m), 1087 (s), 957 (s), 750 (m).
60%	With iodine; silver trifluoroacetate In methanol at 35℃; for 20 h;	A rotor was added to a 25 mL round-bottom flask, and then 0.4 g deoxycytidine was dissolved in 30 mL methanol, and stirred for a few minutes. Iodine (670 mg, 1.5 eq) and silver trifluoroacetate (583 mg, 1.5 eq) were added in sequence, and reacted for about 20 hours at 35° C., and a precipitate silver iodide was generated. After reaction, the reaction solution was filtrated with celite, and washed with methanol, and the filtrate was dried by suction. The product was purified by chromatography on silica gel column (eluting with dichloromethane/methanol=4/1 as a mobile phase), to obtain the following final product ICdR (as shown in Formula 2 below, 370 mg, yield: about 60percent). The chemical structure was identified by nuclear magnetic resonance (NMR) spectrum, and the data was as follows. ¹H NMR (MeOH-d₄, 200 MHz): δ 8.43 (s, 1H, H-6), 6.08 (dd, J=6.0, 6.2 Hz, 1H, H-1'), 4.26 (m, 1H, H-3'), 3.77 (m, 3H, H-4', H-5'), 2.23 (m, 1H, H-2'α), 2.05 (m, 1H, H-2'(3) LRESI(+): 376.0 ([M+Na]⁺); Exact mass (HRMS) calcd for C₉H₁₂IN₃O₄, 352.9872; found 353.9959 ([M+H]⁺); found 375.9780 ([M+Na]⁺)

Reference： [1] Organic Letters, 2010, vol. 12, # 24, p. 5671 - 5673
[2] Patent: WO2012/62907, 2012, A1, . Location in patent: Page/Page column 13; 14
[3] Patent: US2013/237697, 2013, A1, . Location in patent: Paragraph 0052-0055
[4] Synthesis, 2009, # 23, p. 3957 - 3962
[5] Patent: US2012/178919, 2012, A1, . Location in patent: Page/Page column 4
[6] European Journal of Organic Chemistry, 2012, # 17, p. 3278 - 3287
[7] Angewandte Chemie - International Edition, 2016, vol. 55, # 5, p. 1912 - 1916[8] Angew. Chem., 2016, vol. 128, # 5, p. 1946 - 1950,4
[9] Nucleosides, Nucleotides and Nucleic Acids, 2011, vol. 30, # 10, p. 753 - 767

7
[ 64-19-7 ]
[ 951-77-9 ]
[ 32909-05-0 ]

Reference： [1] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 7, p. 2061 - 2064

8
[ 70740-24-8 ]
[ 951-77-9 ]
[ 32909-05-0 ]

Reference： [1] Tetrahedron Letters, 2006, vol. 47, # 25, p. 4201 - 4203

9
[ 108-24-7 ]
[ 951-77-9 ]
[ 32909-05-0 ]

Reference： [1] Nucleosides and Nucleotides, 1997, vol. 16, # 7-9, p. 1589 - 1598
[2] Canadian Journal of Chemistry, 1994, vol. 72, # 11, p. 2225 - 2238

10
[ 951-77-9 ]
[ 32909-05-0 ]

Reference： [1] Tetrahedron, 1981, vol. 37, p. 363 - 369

11
[ 213845-16-0 ]
[ 951-77-9 ]
[ 32909-05-0 ]

Reference： [1] Chemical Research in Toxicology, 1998, vol. 11, # 9, p. 1082 - 1088

12
[ 951-77-9 ]
[ 59-14-3 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 736

[ 951-77-9 ] Synthesis Path-Downstream 1~88

1
[ 951-77-9 ]
[ 2641-80-7 ]

Yield	Reaction Conditions	Operation in experiment
32.1 mg	With 5% rhodium on activated aluminium oxide; hydrogen; In methanol; under 9050.33 Torr;	In an exemplary experiment, DHdC was prepared according to Scheme 3. 2?-Deoxycytidine (284.8 mg, 1.253 mmol) was dissolved in 25 mL MeOH via sonication to form a 0.05 M solution. Three stainless steel cartridges were packed with about 400 mg of Rh/alumina (5%) each and connected in series. The solution was loaded into an 8 mL stainless steel syringe in a syringe pump and connected to the cartridges and a hydrogen gas tank via a Y-linker. The solution and hydrogen gas were pumped through the connected cartridges at a flow rate of 80 IAL/min with hydrogen gas pressure of 175 psi. The outflow was connected in 5 mL fractions and checked via TLC (30% MeOH-NH3 in DCM on silica, starting material Rf=0.29, product Rf=0.14). All fractions showed similar conversion rates and were combined and concentrated via rotary evaporation to 282 mg of a white, sticky solid. Proton NMR showed 80% conversion to product with partial anomerization (20-30% alpha anomer) of the ribose sugar. To purify the beta anomer product, a column of silica gel was prepared using 10% MeOH-NH3 in DCM. The product was dissolved in a minimal amount of MeOH-NH3 in DCM and loaded onto the column. The column was eluted with a gradient of 10-30% MeOH-NH3 in DCM. Fractions that appeared to contain the desired product on TLC were combined and concentrated via rotary evaporation to yield 61.3 mg of a light yellow solid. Proton NMR showed 90% of the desired beta-anomer. The product was repurified using a pipette column prepared with silica gel using 10% MeOH-NH3 in DCM. The product was dissolved in a minimal amount of MeOH-NH3 in DCM and loaded onto the column. The column was eluted with a gradient of 10-20% MeOH-NH3 in DCM. Fractions that appeared to contain the desired product on TLC were combined and concentrated via rotary evaporation to yield 32.1 mg of a light yellow solid. Proton NMR showed full conversion to the desired product with no starting material remaining and <5% of the undesired alpha-anomer

Reference： [1]Journal of Biological Chemistry,1957,vol. 228,p. 601,605,606
[2]Acta Chemica Scandinavica (1947),1957,vol. 11,p. 1081
[3]Patent: US2014/206639,2014,A1 .Location in patent: Paragraph 0154

2
[ 951-77-9 ]
[ 951-78-0 ]

Yield	Reaction Conditions	Operation in experiment
> 99%	With cytidine deaminase enzyme; In aq. phosphate buffer; at 37℃; for 0.0833333h;pH 7.0;Enzymatic reaction;	Comparative Example 3: Deamination of <strong>[951-77-9]2'-deoxycytidine</strong> to 2'-deoxyuridine A 100 mM solution of <strong>[951-77-9]2'-deoxycytidine</strong> (495 muIota_) in 100 mM phosphate buffer at pH 7 was mixed with 50 muIota_ of cytidine deaminase enzyme solution containing >300 AU in phosphate buffer. The reaction was performed at 37C during 5 minutes and stopped with HCI. Then, the crude reaction was filtered through a 10 KDa membrane, and a portion was diluted and analyzed by HPLC-UV-DAD. Product identification was performed by comparison to a standard sample. 2'-Deoxyuridine was obtained in quantitative yield (>99%).

Reference： [1]Patent: WO2016/146808,2016,A1 .Location in patent: Page/Page column 29
[2]Journal of the American Chemical Society,1955,vol. 77,p. 736
[3]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1986,vol. 40,p. 798 - 805
[4]Nucleosides, nucleotides and nucleic acids,2009,vol. 28,p. 614 - 632
[5]Journal of the American Chemical Society,2013,vol. 135,p. 14593 - 14599
[6]Journal of Agricultural and Food Chemistry,2014,vol. 62,p. 1796 - 1801
[7]Patent: US2019/144905,2019,A1 .Location in patent: Paragraph 0020

3
[ 951-77-9 ]
[ 32387-56-7 ]

Reference： [1]Synthesis,2009,p. 3957 - 3962
[2]Journal of Organic Chemistry,1981,vol. 46,p. 2819 - 2823
[3]Organic and Biomolecular Chemistry,2012,vol. 10,p. 1007 - 1013
[4]Journal of the American Chemical Society,1959,vol. 81,p. 1756
[5]Chemical Research in Toxicology,2002,vol. 15,p. 262 - 268
[6]Chemical Research in Toxicology,2010,vol. 23,p. 1293 - 1302

4
[ 951-77-9 ]
[ 1022-79-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium azide; bromoisocyanuric acid monosodium salt; In water; acetonitrile; at 20℃; for 0.5h;	General procedure: 2'-O-Methyluridine (5, 0.103 g, 0.4 mmol) was dissolved in aqueous acetonitrile solution(H2O:CH3CN 1:9, 5 mL) under stirring. NaN3 (0.104 g, 1.6 mmol) was added, followed by addition of SMBI (0.101 g, 0.44 mmol) at r.t. and the mixture was stirred. Progress of the reaction was followedby TLC. On completion of the reaction after 1.5 h, the reaction mixture was filtered, evaporated todryness under reduced pressure and coevaporated with acetonitrile (2 × 2 mL). The crude reactionmixture was purified by column chromatography (4%-6% MeOH in DCM, v/v) to afford bromonucleoside 6 (0.117 g, 93%) in pure form as a white solid

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 1007 - 1013
[2]Synthesis,2009,p. 3957 - 3962
[3]European Journal of Organic Chemistry,2010,p. 4713 - 4718
[4]Molecules,2013,vol. 18,p. 12740 - 12750
[5]Journal of the American Chemical Society,1959,vol. 81,p. 1756
[6]Chemical Research in Toxicology,1996,vol. 9,p. 1145 - 1151
[7]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 5164 - 5170

5
[ 3992-42-5 ]
[ 951-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In methanol;pH 7.0;	EXAMPLE 1Synthesis of Standard 5-iodo-2'-deoxycytidine (ICdR)As the commercially available starting material deoxycytidine hydrochloride is sparsely soluble in methanol, and thus before reaction, deoxycytidine hydrochloride (1 g) was dissolved in methanol (2 mL) first, and then several drops of triethylamine were added for neutralization, till deoxycytidine hydrochloride was completely dissolved. The solution was added to a sample vial containing CH2Cl2, and then large quantities of precipitate were generated, which was filtrated to obtain neutralized deoxycytidine as a solid (as shown in Formula 1).

Reference： [1]Synthesis,1984,p. 965 - 968
[2]Journal of Organic Chemistry,1999,vol. 64,p. 6319 - 6328
[3]Journal of Organic Chemistry,1999,vol. 64,p. 6319 - 6328
[4]Patent: US2012/178919,2012,A1 .Location in patent: Page/Page column 3-4

6
[ 110522-75-3 ]
[ 22882-02-6 ]
[ 951-77-9 ]

Yield	Reaction Conditions	Operation in experiment
0.7 % Chromat.	With ammonia; methylamine In water at 65℃; for 1h; deprotection reagent;

Reference： [1]Reddy, M. P.; Hanna, N. B.; Farooqui, Firdous [Tetrahedron Letters, 1994, vol. 35, # 25, p. 4311 - 4314]

7
[ 32909-05-0 ]
[ 951-77-9 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 4311 - 4314

8
[ 75-77-4 ]
[ 951-77-9 ]
[ 51432-42-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; at 20℃; for 2h;	Synthesis of N4-Trimethoxytrityl-<strong>[951-77-9]2'-deoxycytidine</strong>2'-Deoxynucleoside (10 mmol) was coevaporated three times with pyridine and dried in vacuo for 12 h. Anhydrous pyridine (50 mL) and chlorotrimethylsilane (50 mmol) were added. After the mixture was stirred at room temperature for 2 h, trimethoxytrityl chloride (3.85 g, 10.5 mmol) was added. The reaction was stirred overnight (16 h) at room temperature. Water (60 mL) and aqueous ammonium hydroxide (2 mL, 28-30%) were added, and the reaction mixture was stirred for 30 min. The crude product was extracted into dichloromethane, the organic layer was washed two times with 5% aqueous solution of sodium . The product was filtered and purified by column chromatography using chloroform/pyridine (99.9:0.1) with a gradient of methanol (0-6%). Yield 95%. 1H NMR (DMSO-d6) delta 8.29 (bs, 1H), 7.69 (d, 1H), 7.10 (d, 4H), 6.82 (d, 4H), 6.21 (d, 1H), 6.04 (t, 1H), 5.17 (d, 1H), 4.94 (t, 1H), 4.16-4.14 (m, 1H), 3.72 (s, 9H), 3.51-3.48 (m, 2H), 2.05-1.86 (m, 2H); 13C NMR(DMSO-d6) delta 163.29, 157.37, 154.07, 139.53, 137.26, 129.78, 112.70, 96.38, 87.18, 84.67, 70.65, 68.92, 61.51, 54.98; HRMS (FAB) calcd for C31H33N3O7 (M+) 559.2319, found 559.2331.

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 427 - 430
[2]Journal of the American Chemical Society,1982,vol. 104,p. 1316 - 1319
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 326 - 329
[4]Tetrahedron Letters,1995,vol. 36,p. 9277 - 9280
[5]Journal of Organic Chemistry,1995,vol. 60,p. 8132 - 8133
[6]Nucleosides and Nucleotides,1996,vol. 15,p. 1459 - 1467
[7]Tetrahedron Letters,1998,vol. 39,p. 1139 - 1142
[8]Helvetica Chimica Acta,1999,vol. 82,p. 633 - 644
[9]Chemistry - A European Journal,1999,vol. 5,p. 669 - 681
[10]Tetrahedron Letters,2001,vol. 42,p. 1069 - 1072
[11]Synthetic Communications,2003,vol. 33,p. 1233 - 1243
[12]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 1009 - 1013
[13]Tetrahedron Letters,2004,vol. 45,p. 6287 - 6290
[14]Patent: US2010/10069,2010,A1 .Location in patent: Page/Page column 9
[15]Journal of the American Chemical Society,2011,vol. 133,p. 9844 - 9854

9
[ 108-22-5 ]
[ 951-77-9 ]
[ 72560-70-4 ]

Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 945 - 953

10
[ 63-89-8 ]
[ 951-77-9 ]
[ 114480-64-7 ]

Yield	Reaction Conditions	Operation in experiment
	Streptomyces phospholipase D; Yield given;

Reference： [1]Yanagawa, Hiroshi; Ogawa, Yoko; Furuta, Hiroyuki; Tsuno, Katsushige [Chemistry Letters, 1988, p. 269 - 272]

11
[ 1548-84-1 ]
[ 951-77-9 ]
[ 4836-13-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	In pyridine at 80℃; for 5h;

Reference： [1]Igolen, Jean; Morin, Christophe [Journal of Organic Chemistry, 1980, vol. 45, # 23, p. 4802 - 4804]

12
[ 97-72-3 ]
[ 951-77-9 ]
[ 110522-75-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	In N,N-dimethyl-formamide
71%

Reference： [1]Reddy; Hanna, Naeem B.; Farooqui, Firdous [Nucleosides and Nucleotides, 1997, vol. 16, # 7-9, p. 1589 - 1598]
[2]Vu, Huynh; McCollum, Christie; Jacobson, Karen; Theisen, Pete; Vinayak, Ravi; et al. [Tetrahedron Letters, 1990, vol. 31, # 50, p. 7269 - 7272]

13
[ 98-88-4 ]
[ 951-77-9 ]
[ 4836-13-9 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2010,vol. 29,p. 168 - 177
[2]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 4233 - 4244
[3]Synthesis,1984,p. 965 - 968
[4]Carbohydrate Research,2010,vol. 345,p. 199 - 207
[5]Organic and Biomolecular Chemistry,2012,vol. 10,p. 1510 - 1513

14
[ 93-97-0 ]
[ 951-77-9 ]
[ 4836-13-9 ]

Reference： [1]Synthesis,1984,p. 965 - 968
[2]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 1531 - 1533
[3]Nucleosides, nucleotides and nucleic acids,2002,vol. 21,p. 393 - 400
[4]Organic Letters,2009,vol. 11,p. 1883 - 1886

15
[ 39650-82-3 ]
[ 951-77-9 ]
[ 98533-08-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	In methanol; at 20℃; for 3h;Inert atmosphere;	[00205] Synthesis of 4-N-(N-methylpyrrolidin-2-ylidene)-2?-deoxycytidine (10):[00206] 2.5 g (10 mmol) of 2?-Deoxycytidine hydrate (2a) was suspended in 20 mL of dry methanol. 3.8 g (26 mmol) of 2,2-Dimethoxy-1-methylpyrrolidine was added slowly with constant stirring under the argon.. The reaction was allowed to continue for 3h till the solution become homogenous and pale yellow in colour. After the reaction methanol was removed by rotary evaporation. The sticky residue was washed several times with diethylether to obtain nonsticky solid. The compound was further purified by silica get column chromatography with CH2C12 as the eluent. Methanol (0-20%) was used as the gradient. After removing the solvent thepure compound appeared as a white foam.Yield: 2.61 g (85%); Rf (CH2C12/MeOH 10/2 v/v): 0.3; ?H NMR (CDC13, 400 MHz): 7.91 (d, J=7.8 Hz, 1H), 6.13 (t, J=7.1 Hz, 1H), 6.03 (d, J=8 Hz, 1H), 4.55 (m, 1H), 4.01 (m, 1H), 3.88 (m, 2H), 3.48 (m, 2H), 3.11 (m, 2H), 3.05 (,3H), 2.41 (m, 2H), 2.06 (m, 2H); ?3C NMR (CDC13, 400 MHz): &172.20, 169.00, 156.74, 141.98, 103.40,87.53, 70.17, 61.71, 51.71, 40.56, 31.93, 30.53, 19.71; ESI MS: 309.1583 [MH]

Reference： [1]Journal of the American Chemical Society,1986,vol. 108,p. 2040 - 2048
[2]Patent: WO2015/168461,2015,A2 .Location in patent: Paragraph 00205; 00206

16
[ 951-77-9 ]
[ 1032-65-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 2'-Deoxycytidine With trichlorophosphate at 20℃; for 0.15h; Flow reactor; Green chemistry; Stage #2: With water at 20℃; Flow reactor; Green chemistry; chemoselective reaction;
78%	With tris(p-nitrophenyl)phosphate at 50℃; Erwina herbicola 47/3 cells;
	With Tris-HCl buffer; ATP; diothiothreitol In various solvent(s) at 37℃;

	With recombinant human deoxycytidine kinase (EC 2.7.1.74); ATP In various solvent(s) at 37℃;
	With Tris-HCl buffer; recombinant human cytosolic deoxycytidine kinase; ATP In water; dimethyl sulfoxide at 37℃;
	With ATP; magnesium chloride In various solvent(s) at 25℃;
	Multi-step reaction with 3 steps 1: pyridine 2: pyridine / und Erwaermen des Reaktionsprodukts mit wss.Essigsaeure 3: palladium; ethanol; water / Hydrogenation
	Multi-step reaction with 5 steps 1: pyridine 2: pyridine 3: acetic acid; water 4: pyridine / und Erwaermen des Reaktionsprodukts mit 4-Methyl-morpholin in Benzol 5: palladium; ethanol; water / Hydrogenation
	With recombinant human deoxycytidine kinase, His-tagged; potassium chloride; ATP; magnesium chloride; Cleland's reagent; BSA at 37℃; aq. buffer; Enzymatic reaction;
	With recombinant deoxyribonucleoside kinase AtdNK from Arabidopsis thaliana (ecotype Columbia); ATP In aq. buffer Enzymatic reaction;
	With drosophila melanogaster deoxyribonucleoside kinase; ATP; magnesium chloride In aq. buffer at 37℃; for 24h; Enzymatic reaction;
	With potassium chloride; wild-type deoxycytidine kinase; sodium fluoride; ATP; 2-amino-2-hydroxymethyl-1,3-propanediol; magnesium chloride In aq. buffer at 37℃; Enzymatic reaction;

Reference： [1]Zhu, Chenjie; Tang, Chenglun; Cao, Zhi; He, Wei; Chen, Yong; Chen, Xiaochun; Guo, Kai; Ying, Hanjie [Organic Process Research and Development, 2014, vol. 18, # 11, p. 1575 - 1581]
[2]Zinchenko, A. I.; Barai, V. N.; Mikhailopulo, I. A. [Chemistry of Natural Compounds, 1989, vol. 25, # 5, p. 626 - 627][Khimiya Prirodnykh Soedinenii, 1989, vol. 25, # 5, p. 732 - 733]
[3]Gaubert, Gilles; Mathe, Christophe; Imbach, Jean-Louis; Eriksson, Staffan; Vincenzetti, Silvia; Salvatori, Daniela; Vita, Alberto; Maury, Georges [European Journal of Medicinal Chemistry, 2000, vol. 35, # 11, p. 1011 - 1019]
[4]Johansson, Magnus; Karlsson, Anna [Biochemical Pharmacology, 1995, vol. 50, # 2, p. 163 - 168]
[5]Al-Madhoun, Ashraf Said; Eriksson, Staffan; Wang, Zhi-Xian; Naimi, Ebrahim; Knaus, Edward E.; Wiebe, Leonard I. [Nucleosides, nucleotides and nucleic acids, 2004, vol. 23, # 12, p. 1865 - 1874]
[6]Murakami, Eisuke; Bao, Haiying; Ramesh, Mangala; McBrayer, Tamara R.; Whitaker, Tony; Steuer, Holly M. Micolochick; Schinazi, Raymond F.; Stuyver, Lieven J.; Obikhod, Aleksandr; Otto, Michael J.; Furman, Phillip A. [Antimicrobial Agents and Chemotherapy, 2007, vol. 51, # 2, p. 503 - 509]
[7]Michelson; Todd [Journal of the Chemical Society, 1954, p. 34,37]
[8]Michelson; Todd [Journal of the Chemical Society, 1954, p. 34,37]
[9]Location in patent: experimental part Golitsina, Nina L.; Danehy Jr., Francis T.; Fellows, Ross; Cretton-Scott, Erika; Standring, David N. [Antiviral Research, 2010, vol. 85, # 3, p. 470 - 481]
[10]Clausen, Anders R.; Girandon, Lenart; Ali, Ashfaq; Knecht, Wolfgang; Rozpedowska, Elzbieta; Sandrini, Michael P. B.; Andreasson, Erik; Munch-Petersen, Birgitte; Piskur, Jure [FEBS Journal, 2012, vol. 279, # 20, p. 3889 - 3897]
[11]Serra, Immacolata; Conti, Silvia; Piskur, Jure; Clausen, Anders R.; Munch-Petersen, Birgitte; Terreni, Marco; Ubiali, Daniela [Advanced Synthesis and Catalysis, 2014, vol. 356, # 2-3, p. 563 - 570]
[12]Wang, Danyang; Zhang, Yu; Kleiner, Ralph E. [Journal of the American Chemical Society, 2020, vol. 142, # 34, p. 14417 - 14421]

17
[ 951-77-9 ]
[ 137017-42-6 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8148 - 8150
[2]Chemistry Letters,1991,p. 1591 - 1594

18
[ 108-24-7 ]
[ 951-77-9 ]
[ 32909-05-0 ]

Reference： [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1589 - 1598
[2]Canadian Journal of Chemistry,1994,vol. 72,p. 2225 - 2238

19
[ 452-06-2 ]
[ 951-77-9 ]
[ 3616-24-8 ]

Reference： [1]Nucleosides and Nucleotides,1995,vol. 14,p. 805 - 808

20
[ 16114-05-9 ]
[ 951-77-9 ]
1-(2-deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-4-yl)pyrimidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With chloro-trimethyl-silane In toluene 1.) r.t., 0.5 h, 2.) 70 deg C, 17 h;

Reference： [1]Miles; Samano; Robins [Journal of Organic Chemistry, 1995, vol. 60, # 21, p. 7066 - 7069]

21
[ 69304-37-6 ]
[ 951-77-9 ]
[ 102434-71-9 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 13427 - 13441
[2]Angewandte Chemie - International Edition in English,1997,vol. 36,p. 647 - 649
[3]Chemistry - A European Journal,2012,vol. 18,p. 8024 - 8027

22
[ 1032-65-1 ]
[ 951-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	With cerium(III) chloride; HEPES buffer; oxygen In water at 50℃;
	With phosphate buffer; D-glucose; Xantomonas maltophilia at 30℃; for 40h;

Reference： [1]Miyama, Sachiko; Asanuma, Hiroyuki; Komiyama, Makoto [Journal of the Chemical Society. Perkin Transactions 2 (2001), 1997, # 9, p. 1685 - 1688]
[2]Chmielowiec, Urszula; Kruszewska, Hanna; Cybulski, Jacek [Il Farmaco, 1999, vol. 54, # 9, p. 611 - 614]

23
[ 172163-62-1 ]
[ 951-77-9 ]
d(I⁷c⁷G-C)4 [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1997,vol. 80,p. 1809 - 1822

24
[ 110522-75-3 ]
[ 951-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In methanol; water for 0.02h; microwave irradiation;

Reference： [1]Gupta; Kumar [Nucleosides and Nucleotides, 1998, vol. 17, # 9-11, p. 1761 - 1766]

25
[ 18162-48-6 ]
[ 951-77-9 ]
[ 51549-29-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 14h;	Synthesis was performed according to the method described in the literature, using <strong>[951-77-9]2'-deoxycytidine</strong> (13) as a starting material. 1H NMR spectrum was consistent with the literature value.
85%	With 1H-imidazole; In N,N-dimethyl-formamide; at 22℃; for 3h;	To a solution of 2?-deoxycytidine (1.0 g, 4.40 mol) in DMF (5 mL) was added tert-butyldimethylsilyl chloride (2.65 g, 17.6 mol) and imidazole (2.39 g, 35.1 mol). The reaction mixture was stirred at 22 C for 3 h. The solvent was removed in vacuo and the crude product was purified by flash silica gel column chromatography, using a gradient elution (CH2Cl2:MeOH; 98:2 to 94:6) to give compound 11 as a white solid (1.7 g, 85% yield).
	With 1H-imidazole; In N,N-dimethyl-formamide;	The synthesis of the caged phosphoramidite 33 of deoxycytidine follows the same route as the synthesis of 27, as shown in Scheme 5: TBDMS protection of 28, NPOM caging of 29, desilylation from 30 to 31, selective DMT protection to 32, followed by finial activation of the phosphoramidite.

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 15040 - 15041
[2]Patent: US2019/270765,2019,A1 .Location in patent: Paragraph 0188; 0192
[3]Organic and Biomolecular Chemistry,2013,vol. 11,p. 5605 - 5614
[4]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 219 - 227
[5]Nucleosides and Nucleotides,1999,vol. 18,p. 1079 - 1082
[6]Chemistry - A European Journal,2007,vol. 13,p. 311 - 318
[7]Patent: US8247540,2012,B2 .Location in patent: Page/Page column 31-32

26
[ 213845-16-0 ]
[ 951-77-9 ]
[ 32909-05-0 ]

Reference： [1]Chemical Research in Toxicology,1998,vol. 11,p. 1082 - 1088

27
[ 265137-12-0 ]
[ 64395-31-9 ]
[ 1032-65-1 ]
2'-isodeoxy-adenosine 3'-monophosphate [ No CAS ]
[ 951-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphodiesterase I In various solvent(s) at 37℃; for 1h; Enzymatic reaction;

Reference： [1]Taktakishvili, Michael; Neamati, Nouri; Pommier, Yves; Pal, Suresh; Nair, Vasu [Journal of the American Chemical Society, 2000, vol. 122, # 24, p. 5671 - 5677]

28
N⁴-5'-O-di(triphenylmethyl)-2'-deoxycytidine [ No CAS ]
[ 951-77-9 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 5077 - 5088

29
[ 951-77-9 ]
[ 23662-75-1 ]
[ 85819-69-8 ]

Reference： [1]Chemical Research in Toxicology,1996,vol. 9,p. 1140 - 1144

30
[ 700-06-1 ]
[ 951-77-9 ]
1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-[(1H-indol-3-ylmethyl)-amino]-1H-pyrimidin-2-one [ No CAS ]

Reference： [1]Chemical Research in Toxicology,2001,vol. 14,p. 1014 - 1024

31
[ 71-30-7 ]
[ 50-89-5 ]
[ 951-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; piperidine-1-propanesulfonic acid; In water; at 40℃;Enzymatic reaction;	An enzyme sample was added to a 20 mmol/L MOPS-sodium hydroxide buffer (pH 6.0) containing thymidine (5 mmol/L) and cytosine (5 mmol/L), and the mixture was maintained at 40 C. After completion of reaction, the enzyme was inactivated through boiling for one minute. The amount of 2'-deoxycytidine that has been formed was quantitated by HPLC. The activity of the enzyme that forms 1 mumole of 2'-deoxycytidine at 40 C. in one minute was defined as an activity of 1 unit. <Determination of Nucleosidase Activity>

Reference： [1]Bioscience, Biotechnology and Biochemistry,2003,vol. 67,p. 989 - 995
[2]Patent: US2005/170470,2005,A1 .Location in patent: Page/Page column 5

32
[ 24424-99-5 ]
[ 951-77-9 ]
N⁴,N⁴-bis(tert-butoxycarbonyl)-2'-deoxycytidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31.89%		To solution of compound-3 (300 g, i.32i mol) in hexamethyldisilazane (638 g, 3.964 mol) is added DMAP (i6.ii g, 0.i32 mol) followed by TMSOTf (7.22 g, 0.039 mol) is added atC and the resulting reaction mixture is stirred for i h at room temperature. After complete of starting material Boc-anhydride (i.4 L, 6.605 mol) is added at 0 C for i h and the reaction mixture is stirred for i6 h at room temperature. To the reaction is added methanol (3 L)followed by triethylamine (i.5 L) is added at 0 C for i h and the reaction mixture is stirred for20 h at room temperature. Reaction mixture is concentrated under reduced pressure to get crude compound. Crude compound is diluted with ethyl acetate (3 L) and washed with water (i.0 L)and brine (i .0 L) solution; organic layer is dried over anhydrous Na2SO4, filtered and the solvent is evaporated under reduced pressure to get afford crude compound. The crude compound is purified by column chromatography silica gel (100-200 mesh) compound eluted 0 - 3 % MeOH in DCM to afford Compound-4 (180 g, 31.89 %) as off white solid. H-NMR (300 MHz, DMSOd6) 8.41 (d, I = 7.5 Hz, 1H), 6.84 (d, I = 7.5 Hz, 1H), 6.06 (t, I = 6.2 Hz, 1H), 5.28 (d, I = 4.3Hz, 1H), 5.07 (q, I = 4.6, 4.0 Hz, 1H), 4.21 (q, I = 4.1 Hz, 1H), 3.87 (q, I = 3.7 Hz, 1H), 3.71 -3.49 (m, 2H), 2.32 (m, 1H), 2.03 (dt, I = 13.0, 6.2 Hz, 1H), 1.49 (s, 18H). LC-MS: 275 (M + H).
31.89%		To solution of compound-3 (300 g, 1.321 mol) in Hexamethyldisilazane (638 g, 3.964 mol) is added DMAP (16.11 g, 0.132 mol) followed by TMSOTf (7.22 g, 0.039 mol) is added at 0 C. and the resulting reaction mixture is stirred for 1 h at room temperature. After complete of starting material Boc-anhydride (1.4 L, 6.605 mol) is added at 0 C. for 1 h and the reaction mixture is stirred for 16 h at room temperature. To the reaction is added methanol (3 L) followed by triethylamine (1.5 L) is added at 0 C. for 1 h and the reaction mixture is stirred for 20 h at room temperature. Reaction mixture is concentrated under reduced pressure to get crude compound. Crude compound is diluted with ethyl acetate (3 L) and washed with water (1.0 L) and brine (1.0 L) solution; Organic layer is dried over anhydrous Na2SO4, filtered and the solvent is evaporated under reduced pressure to get afford crude compound. The Crude compound is purified by column Chromatography silica gel (100-200 mesh) Compound eluted 0-3% MeOH in DCM to afford compound-4 (180 g, 31.89%) as off white solid. H-NMR (300 MHz, DMSO-d6) delta 8.41 (d, J=7.5 Hz, 1H), 6.84 (d, J=7.5 Hz, 1H), 6.06 (t, J=6.2 Hz, 1H), 5.28 (d, J=4.3 Hz, 1H), 5.07 (q, J=4.6, 4.0 Hz, 1H), 4.21 (q, J=4.1 Hz, 1H), 3.87 (q, J=3.7 Hz, 1H), 3.71-3.49 (m, 2H), 2.32 (m, 1H), 2.03 (dt, J=13.0, 6.2 Hz, 1H), 1.49 (s, 18H). LC-MS: 275 (M+H).
31.89%		To solution of compound-3 (300 g, 1.321 mol) in hexamethyldisilazane (638 g, 3.964 mol) is added DMAP (16.11 g, 0.132 mol) followed by TMSOTf (7.22 g, 0.039 mol) is added at 0 C. and the resulting reaction mixture is stirred for 1 h at room temperature. After complete of starting material Boc-anhydride (1.4 L, 6.605 mol) is added at 0 C. for 1 h and the reaction mixture is stirred for 16 h at room temperature. To the reaction is added methanol (3 L) followed by triethylamine (1.5 L) is added at 0 C. for 1 h and the reaction mixture is stirred for 20 h at room temperature. Reaction mixture is concentrated under reduced pressure to get crude compound. Crude compound is diluted with ethyl acetate (3 L) and washed with water (1.0 L) and brine (1.0 L) solution; organic layer is dried over anhydrous Na2SO4, filtered and the solvent is evaporated under reduced pressure to get afford crude compound. The crude compound is purified by column chromatography silica gel (100-200 mesh) compound eluted 0-3% MeOH in DCM to afford Compound-4 (180 g, 31.89%) as off white solid. H-NMR (300 MHz, DMSO-d6) delta 8.41 (d, J=7.5 Hz, 1H), 6.84 (d, J=7.5 Hz, 1H), 6.06 (t, J=6.2 Hz, 1H), 5.28 (d, J=4.3 Hz, 1H), 5.07 (q, J=4.6, 4.0 Hz, 1H), 4.21 (q, J=4.1 Hz, 1H), 3.87 (q, J=3.7 Hz, 1H), 3.71-3.49 (m, 2H), 2.32 (m, 1H), 2.03 (dt, J=13.0, 6.2 Hz, 1H), 1.49 (s, 18H). LC-MS: 275 (M+H).

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5888 - 5891
[2]Patent: WO2018/165675,2018,A1 .Location in patent: Page/Page column 69; 71; 72; 73
[3]Patent: US2018/353529,2018,A1 .Location in patent: Paragraph 0168
[4]Patent: US2020/121708,2020,A1 .Location in patent: Paragraph 0126-0128; 0134; 0136

33
[ 70740-24-8 ]
[ 951-77-9 ]
[ 32909-05-0 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 4201 - 4203

34
[ 951-77-9 ]
[ 49757-42-8 ]
[ 845306-87-8 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 8138 - 8139
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2008,vol. 183,p. 349 - 363
[3]Phosphorus, Sulfur and Silicon and the Related Elements,2011,vol. 186,p. 921 - 932

35
[ 609-73-4 ]
[ 951-77-9 ]
N⁶-2-nitrobenzen-1-yl-2'-deoxycytidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5599 - 5606

36
[ 951-77-9 ]
[ 4836-13-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₂O; pyridine / 0.5 h / 20 °C 2: pyridine / 4 h / 20 °C 3: aq. NH₄OH / 0.25 h / 20 °C
	Multi-step reaction with 2 steps 1: 98 percent / iPr₂NEt; DMAP / dimethylformamide / 0.02 h / microwave irradiation 2: 98 percent / 0.2 N NaOH / pyridine; methanol / 0 h / microwave irradiation
	Multi-step reaction with 3 steps 1: pyridine 2: 2 h / 20 °C 3: NH₄OH / H₂O / 0.33 h / 0 °C

	Multi-step reaction with 3 steps 1: pyridine / 0.25 h 2: pyridine / 1 h / Ambient temperature 3: NH₃ / pyridine; H₂O / 0.5 h
	Multi-step reaction with 3 steps 1: pyridine / 0.25 h 2: pyridine / 2 h / Ambient temperature 3: 29percent aq. ammonia / pyridine / 0.25 h / Ambient temperature
	Multi-step reaction with 2 steps 1: pyridine / 0 °C 2: 1N NaOH / dioxane / 0.33 h

Reference： [1]Zhu, Xue-Feng; Williams Jr., Howard J.; Scott, A. Ian [Synthetic Communications, 2003, vol. 33, # 7, p. 1233 - 1243]
[2]Rao; Kumar; Chauhan; Garg; Gupta [Nucleosides, nucleotides and nucleic acids, 2002, vol. 21, # 4-5, p. 393 - 400]
[3]Busson; Kerremans; Van Aerschot; Peeters; Blaton; Herdewijn [Nucleosides and Nucleotides, 1999, vol. 18, # 4-5, p. 1079 - 1082]
[4]Grotli, Morten; Eritja, Ramon; Sproat, Brian [Tetrahedron, 1997, vol. 53, # 33, p. 11317 - 11346]
[5]Ti, G. S.; Gaffney, B. L.; Jones, R. A. [Journal of the American Chemical Society, 1982, vol. 104, # 5, p. 1316 - 1319]
[6]Koester, Hubert; Kulikowski, Konrad; Liese, Thomas; Heikens, Wiebke; Kohli, Vipin [Tetrahedron, 1981, vol. 37, p. 363 - 369]

37
[ 22224-41-5 ]
[ 951-77-9 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 5969 - 5985

38
[ 951-77-9 ]
[ 100898-63-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 98 percent / dimethylformamide 2: 85 percent / pyridine
	Multi-step reaction with 2 steps 1: methanol / 3 h / Heating 2: pyridine, 4-dimethylaminopyridine / 32 h / Ambient temperature

Reference： [1]Reddy; Hanna, Naeem B.; Farooqui, Firdous [Nucleosides and Nucleotides, 1997, vol. 16, # 7-9, p. 1589 - 1598]
[2]Whitfield; Douglas; Tang; Csizmadia; Pang; Moolten; Krepinsky [Canadian Journal of Chemistry, 1994, vol. 72, # 11, p. 2225 - 2238]

39
[ 951-77-9 ]
[ 154110-40-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 98 percent / dimethylformamide 2: 85 percent / pyridine 3: 85 percent / iPr₂NEt / tetrahydrofuran

Reference： [1]Reddy; Hanna, Naeem B.; Farooqui, Firdous [Nucleosides and Nucleotides, 1997, vol. 16, # 7-9, p. 1589 - 1598]

40
[ 85335-73-5 ]
[ 951-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 4-N,N-dimethylaminopyridine / acetonitrile / 0.75 h / Ambient temperature 2: n-Bu₃SnH, AIBN / toluene / 14 h / 75 °C 3: 1.) TBAF, 2.) NH₃ / 1.) THF, 75 deg C, 3 h, 2.) MeOH, room temperature

Reference： [1]Robins; Wilson; Hansske [Journal of the American Chemical Society, 1983, vol. 105, # 12, p. 4059 - 4065]

41
[ 3768-18-1 ]
[ 951-77-9 ]

Reference： [1]Journal of the American Chemical Society,1983,vol. 105,p. 4059 - 4065

42
[ 951-77-9 ]
[ 67219-55-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: 29percent aq. ammonia, 4-dimethylaminopyridine / pyridine; triethylamine / 0.5 h
	Multi-step reaction with 2 steps 1: 1.) pyridine, 2.) aq. NaOH / 1.) 3 h, room temp., 2.) THF, MeOH, H₂O, 15 min, 0 deg C 2: 86 percent / pyridine / 1 h / Ambient temperature
	Multi-step reaction with 2 steps 1: 86 percent / methanol / 10 h / Heating 2: 86 percent / pyridine / 1 h / Ambient temperature

	Multi-step reaction with 2 steps 1: pyridine / 15 h / 80 °C 2: 80 percent / pyridine / 1 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

Reference： [1]Ti, G. S.; Gaffney, B. L.; Jones, R. A. [Journal of the American Chemical Society, 1982, vol. 104, # 5, p. 1316 - 1319]
[2]Charubala, R.; Uhlmann, E.; Beiter, A. H.; Pfleiderer, W. [Synthesis, 1984, # 11, p. 965 - 968]
[3]Charubala, R.; Uhlmann, E.; Beiter, A. H.; Pfleiderer, W. [Synthesis, 1984, # 11, p. 965 - 968]
[4]Igolen, Jean; Morin, Christophe [Journal of Organic Chemistry, 1980, vol. 45, # 23, p. 4802 - 4804]
[5]Janczyk, Matthaeus; Appel, Bettina; Springstubbe, Danilo; Fritz, Hans-Joachim; Mueller, Sabine [Organic and Biomolecular Chemistry, 2012, vol. 10, # 8, p. 1510 - 1513]

43
[ 951-77-9 ]
[ 7481-89-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 85 percent / ethanol / 2 h / Heating 2: 72 percent / pyridine / 70 h / Ambient temperature 3: 87 percent / pyridine / 1.5 h / Ambient temperature 4: 63 percent / LiI / ethyl acetate / 2.5 h / Heating 5: 94 percent / triethylamine / Pd/C / 1,2-dimethoxy-ethane / 1.25 h / 1810.02 Torr 6: 90 percent / HCl-EtOH / ethyl acetate / 0.5 h / 10 - 15 °C 7: 75 percent / ammonia / methanol / 22 h / Ambient temperature; pH 12

Reference： [1]Kaskar; Markovac [Journal of Heterocyclic Chemistry, 1989, vol. 26, # 6, p. 1531 - 1533]

44
[ 951-77-9 ]
[ 32909-05-0 ]

Reference： [1]Tetrahedron,1981,vol. 37,p. 363 - 369

45
[ 951-77-9 ]
[ 110522-75-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine 2: triethylamine, water, pyridine

Reference： [1]Schulhof, J. C.; Molko, D.; Teoule, R. [Tetrahedron Letters, 1987, vol. 28, # 1, p. 51 - 54]

46
[ 951-77-9 ]
[ 59-14-3 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 736

47
[ 712352-51-7 ]
[ 951-77-9 ]
4-[{2-[1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylcarbamoyl]-5-phenyl-thiophen-3-yl}-(4-methyl-cyclohexanecarbonyl)-amino]-1-methyl-piperidinium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; N-ethyl-N,N-diisopropylamine;HATU; In DMF (N,N-dimethyl-formamide); at 20℃;	A solution of 4- [ (2-CARBOXY-5-PHENYL-THIOPHEN-3-YL)- (4- METHYL-CYCLOHEXANECARBONYL)-AMINO]-1-METHYL- piperidinium chloride in DMF is treated with 2'-DOXY- cytidine (L. OEQ), HATU (L. leq), di-isopropylethylamine (2. OEQ) and DMAP (0. leq). The reaction is stirred at room temperature. EtOAc and NAHC03 (aq) is added and the organic layer is washed with water and brine, dried and evaporated to a residue that is purified by silica gel column chromatography to provide the desired compound.

Reference： [1]Patent: WO2004/52879,2004,A1 .Location in patent: Page 47

48
[ 108-24-7 ]
[ 951-77-9 ]
[ 61671-83-8 ]

Yield	Reaction Conditions	Operation in experiment
67%	With pyridine; for 4h;	500 mg <strong>[951-77-9]2'-deoxycytidine</strong> (CdR) is reacted with acetic anhydride (Ac20) as a protecting agent at a molar ratio of 1: 4.5 for 4 hours with pyridine as a solvent. The reaction is monitored by TLC (developing solution: methanol (MuOmicronEta): dichloromethane (DCM) = 1: 19), product Rf=0.3. Followed by extraction of pyridine, then added the 5mL of H20, extraction with DCM (5mL * 3), collecting the organic layer. Extraction of DCM, toluene 25mL azeotropic total of 3 times, remove the residual pyridine, Ac20, and finally with DCM 20mL azeotropic total of three times to remove toluene. Then obtained 4-acetoamide-(2?-deoxy-3?-acetate-5'-acetoxymethyl) cytidine) (CdR-(OAc) 3):520mg. Yield 67%.

Reference： [1]Patent: TWI529153,2016,B .Location in patent: Page/Page column 8
[2]Chemical Research in Toxicology,2006,vol. 19,p. 1611 - 1618

49
[ 951-77-9 ]
[ 611-53-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With iodine; 3-chloro-benzenecarboperoxoic acid; In N,N-dimethyl-formamide; at 20℃; for 2h;	dC 1 In a flame dried round bottom flask 10.0 g dC (44.0 mmol, 1.0 eq), 7.70 g iodine (26.4 mmol, 0.6 eq) and 1 1.4 g mCPBA (70 %, 46.2 mmol, 1 .05 eq) were dissolved in 120 mL DMF. The reaction mixture was stirred 2 h at room temperature and subsequently evaporated to dryness, (small amounts of DMF are tolerable during subsequent column chromatography) Purification by column chromatography (DCM/MeOH/H20/NH3 190:10:0.6:0.6 ? 90:10:0.6:0.6) yielded 9.71 g (63 %) of 1 as an orange solid. 1H NMR (400 MHz, CDCI3/MeOD) delta (ppm) = 8.46 (s, 1 H), 6.13 (t, 3J=6.0, 1 H), 4.34 (dt, 3J=4.7, 3J=6.3 , 1 H), 3.93 (dt, 3J=3.0, 3J=4.3, 1 H), 3.84 (dd, 3J=3.0 Hz, 2J=12.1 , 1 H), 3.72 (dd, 3 =3.2, 2J=12.1 , 1 H), 2.39 (ddd, 3J=4.8, 3J=6.3, 2J=13.7, 1 H), 2.20 - 2.09 (m, 1 H). 13C NMR (101 MHz, MeOD) delta (ppm) = 163.9, 153.9, 150.9, 89.5, 88.3, 71 .5, 62.2, 56.2, 42.5. HRMS (ESI +) calculated for C9H13IN304+ [M+H]+: 353.9945, found: 353.9944. melting range: 133C - 135 C (decomposition) IR (ATR): 3191 (w), 1718 (m), 1642 (s), 1286 (m), 1087 (s), 957 (s), 750 (m).
63%	With iodine; 3-chloro-benzenecarboperoxoic acid; In N,N-dimethyl-formamide; at 20℃; for 2h;Inert atmosphere;	5-(Iodo)deoxycytidine (1) In a flame dried round bottom flask 10.0 g dC (44.0 mmol, 1.0 eq), 7.70 g iodine (26.4 mmol, 0.6 eq) and 11.4 g mCPBA (70%, 46.2 mmol, 1.05 eq) were dissolved in 120 mL DMF. The reaction mixture was stirred 2 h at room temperature and subsequently evaporated to dryness. (small amounts of DMF are tolerable during subsequent column chromatography) Purification by column chromatography (DCM/MeOH/H2O/NH3 190:10:0.6:0.6?90:10:0.6:0.6) yielded 9.71 g (63%) of 1 as an orange solid. 1H NMR (400 MHz, CDCl3/MeOD) delta (ppm)=8.46 (s, 1H), 6.13 (t, 3J=6.0, 1H), 4.34 (dt, 3J=4.7, 3J=6.3, 1H), 3.93 (dt, 3J=3.0, 3J=4.3, 1H), 3.84 (dd, 3J=3.0 Hz, 2J=12.1, 1H), 3.72 (dd, 3J=3.2, 2J=12.1, 1H), 2.39 (ddd, 3J=4.8, 3J=6.3, 2J=13.7, 1H), 2.20-2.09 (m, 1H). 13C NMR (101 MHz, MeOD) delta (ppm)=163.9, 153.9, 150.9, 89.5, 88.3, 71.5, 62.2, 56.2, 42.5. HRMS (ESI+) calculated for C9H13IN3O4+[M+H]+: 353.9945, found: 353.9944. melting range: 133 C.-135 C. (decomposition) IR (ATR): 3191 (w), 1718 (m), 1642 (s), 1286 (m), 1087 (s), 957 (s), 750 (m).
60%	With iodine; silver trifluoroacetate; In methanol; at 35℃; for 20h;	A rotor was added to a 25 mL round-bottom flask, and then 0.4 g deoxycytidine was dissolved in 30 mL methanol, and stirred for a few minutes. Iodine (670 mg, 1.5 eq) and silver trifluoroacetate (583 mg, 1.5 eq) were added in sequence, and reacted for about 20 hours at 35 C., and a precipitate silver iodide was generated. After reaction, the reaction solution was filtrated with celite, and washed with methanol, and the filtrate was dried by suction. The product was purified by chromatography on silica gel column (eluting with dichloromethane/methanol=4/1 as a mobile phase), to obtain the following final product ICdR (as shown in Formula 2 below, 370 mg, yield: about 60%). The chemical structure was identified by nuclear magnetic resonance (NMR) spectrum, and the data was as follows. 1H NMR (MeOH-d4, 200 MHz): delta 8.43 (s, 1H, H-6), 6.08 (dd, J=6.0, 6.2 Hz, 1H, H-1'), 4.26 (m, 1H, H-3'), 3.77 (m, 3H, H-4', H-5'), 2.23 (m, 1H, H-2'alpha), 2.05 (m, 1H, H-2'(3) LRESI(+): 376.0 ([M+Na]+); Exact mass (HRMS) calcd for C9H12IN3O4, 352.9872; found 353.9959 ([M+H]+); found 375.9780 ([M+Na]+)

Reference： [1]Organic Letters,2020,vol. 22,p. 41 - 45
[2]Organic Letters,2010,vol. 12,p. 5671 - 5673
[3]Patent: WO2012/62907,2012,A1 .Location in patent: Page/Page column 13; 14
[4]Patent: US2013/237697,2013,A1 .Location in patent: Paragraph 0052-0055
[5]Synthesis,2009,p. 3957 - 3962
[6]Patent: US2012/178919,2012,A1 .Location in patent: Page/Page column 4
[7]European Journal of Organic Chemistry,2012,p. 3278 - 3287
[8]Angewandte Chemie - International Edition,2016,vol. 55,p. 1912 - 1916
Angew. Chem.,2016,vol. 128,p. 1946 - 1950,4
[9]Nucleosides, nucleotides and nucleic acids,2011,vol. 30,p. 753 - 767

50
[ 3226-65-1 ]
[ 951-77-9 ]
[ 838-07-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 260 - 265

51
[ 67-68-5 ]
[ 951-77-9 ]
[ 838-07-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 260 - 265

52
calf thymus DNA, γ-irradiated [ No CAS ]
[ 31077-24-4 ]
[ 105929-27-9 ]
[ 961-07-9 ]
[ 88847-89-6 ]
[ 117182-88-4 ]
(5'R)-5',8-cyclo-2'-deoxyadenosine [ No CAS ]
(5'R)-5',8-cyclo-2'-deoxyguanosine [ No CAS ]
[ 951-77-9 ]
[ 50-89-5 ]
[ 958-09-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3211 - 3219

53
[ 64-19-7 ]
[ 951-77-9 ]
[ 32909-05-0 ]

Reference： [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 2061 - 2064

54
[ 65-85-0 ]
[ 951-77-9 ]
[ 4836-13-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In dichloromethane at 20℃; Stage #2: 2'-Deoxycytidine In dichloromethane; N,N-dimethyl-formamide at 20 - 50℃;

Reference： [1]Location in patent: experimental part Rode, Ambadas B.; Son, Sang Jun; Hong, In Seok [Bulletin of the Korean Chemical Society, 2010, vol. 31, # 7, p. 2061 - 2064]

55
C₁₇H₁₄N₃O₆Pol [ No CAS ]
[ 88-96-0 ]
[ 951-77-9 ]

Reference： [1]Molecules,2010,vol. 15,p. 7509 - 7531

56
[ 108-24-7 ]
[ 951-77-9 ]
[ 65919-98-4 ]

Reference： [1]Organic Letters,2020,vol. 22,p. 41 - 45
[2]Journal of the American Chemical Society,2011,vol. 133,p. 796 - 807

57
[ 951-77-9 ]
[ 1186526-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	With deuterium;palladium 10% on activated carbon; In water-d2; at 160℃; for 24h;Sealed tube;	Example 15-D-Deoxycytidine from Deoxycytidine Deoxycytidine (227 mg, 1 mmol, Aldrich) was dissolved in 4 ml of D2O. 10% Pd/C (27 mg, 10 wt % of the substrate, Aldrich) was added, and the mixture was stirred at 160 C. in a sealed tube under D2 atmosphere for 24 h. After cooling to RT, the reaction mixture was filtered using a membrane filter (Millipore Millex-LG). The filtered catalyst was washed with boiling water (150 ml), and the combined aqueous fractions were evaporated in vacuo, and then again dissolved in H2O and evaporated (5×25 ml) to give 5-D-deoxycytidine as a white solid (206 mg). The structure of the nucleoside was confirmed by MALDI-TOF (Voyager Elite, PerSeptive Biosystems), with HPA as a matrix. Found: 228.225 (45%; MI); 229.229 (27%; Double-deuterated product; MI).

Reference： [1]Patent: US2011/82100,2011,A1 .Location in patent: Page/Page column 5

58
C₉₈H₁₂₂FN₄₀O₅₆P₉S [ No CAS ]
[ 890-38-0 ]
[ 869355-51-1 ]
[ 961-07-9 ]
[ 951-77-9 ]
[ 50-89-5 ]
[ 958-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Crotalus adamanteus venom phosphodiesterase I; bovine intestinal mucosa alkaline phosphatase; water; magnesium chloride; at 37℃; for 18h;pH 7.0;aq. phosphate buffer; Enzymatic reaction;	General procedure: Column containing solid support with the synthesized oligonucleotide was attached to a syringe containing 2 mL of 0.4 M solution of DBU in anhydr CH3CN. Approx. 0.7 mL of the solution was pushed into the column, replaced by a new portion after 5 min and another one after next 5 min. After total time of 15 min the support was washed with dry CH3CN (10 mL) and dried in vacuo. The dried support was placed into a vial, 1 mL of approx. 22% methanolic ammonia was added and the vial closed tightly. After 3 h at rt the solid was filtered off, washed with methanol and water and the filtrates were evaporated. The residue was dissolved in 0.1 m ammonium acetate (1 mL) and passed through a NAP 25 column. The column was washed with the same solution and 6 fractions of 1.4 mL were collected and checked by UV. The oligomer was present mainly in the fractions 3 and 4, with some residue in 5th fraction. Combined fractions were evaporated, dissolved in H2O/acetonitrile, 95/5, v/v (1 mL) and purified by HPLC (two 500 mul injections, Waters XBridge OST C18 Column, 2.5 mum,10 × 50 mm, phase A = 0.1 M TEAA, B = 0.1 M TEAA/Acetonitrile, 50/50, v/v, flow rate 1 ml/min, T = 40 C, gradient 17-20%B in 10 min, then to 50%B in 5 min. Combined fractions were concentrated to approx. 0.5 mL and desalted by passage through HPLC column. Yields of the oligomers BS3-BS6 see Table 1. The oligomerswere verified by enzymatic digestion, results see Table 3. Enzymatic digestion conditions: 0.2 OD of oligonucleotide in 150 muL of buffer (10 mM KH2PO4, 10 mM MgCl2, pH 7) was digested with alkaline phosphatase bovine intestinal mucosa (27 DEA units, Sigma-Aldrich, BioUltra) and phosphodiesterase I from Crotalus adamanteus venom (0.0055 units, Sigma-Aldrich, Purified) for 18 h at 37 C. The enzyme caused partial deamination of dA to dI (confirmed in model experiment).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6098 - 6106

59
C₉₈H₁₂₂FN₄₀O₅₆P₉S [ No CAS ]
[ 890-38-0 ]
[ 869355-51-1 ]
[ 961-07-9 ]
[ 951-77-9 ]
[ 50-89-5 ]
[ 958-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Crotalus adamanteus venom phosphodiesterase I; bovine intestinal mucosa alkaline phosphatase; water; magnesium chloride; at 37℃; for 18h;pH 7.0;aq. phosphate buffer; Enzymatic reaction;	General procedure: Column containing solid support with the synthesized oligonucleotide was attached to a syringe containing 2 mL of 0.4 M solution of DBU in anhydr CH3CN. Approx. 0.7 mL of the solution was pushed into the column, replaced by a new portion after 5 min and another one after next 5 min. After total time of 15 min the support was washed with dry CH3CN (10 mL) and dried in vacuo. The dried support was placed into a vial, 1 mL of approx. 22% methanolic ammonia was added and the vial closed tightly. After 3 h at rt the solid was filtered off, washed with methanol and water and the filtrates were evaporated. The residue was dissolved in 0.1 m ammonium acetate (1 mL) and passed through a NAP 25 column. The column was washed with the same solution and 6 fractions of 1.4 mL were collected and checked by UV. The oligomer was present mainly in the fractions 3 and 4, with some residue in 5th fraction. Combined fractions were evaporated, dissolved in H2O/acetonitrile, 95/5, v/v (1 mL) and purified by HPLC (two 500 mul injections, Waters XBridge OST C18 Column, 2.5 mum,10 × 50 mm, phase A = 0.1 M TEAA, B = 0.1 M TEAA/Acetonitrile, 50/50, v/v, flow rate 1 ml/min, T = 40 C, gradient 17-20%B in 10 min, then to 50%B in 5 min. Combined fractions were concentrated to approx. 0.5 mL and desalted by passage through HPLC column. Yields of the oligomers BS3-BS6 see Table 1. The oligomerswere verified by enzymatic digestion, results see Table 3. Enzymatic digestion conditions: 0.2 OD of oligonucleotide in 150 muL of buffer (10 mM KH2PO4, 10 mM MgCl2, pH 7) was digested with alkaline phosphatase bovine intestinal mucosa (27 DEA units, Sigma-Aldrich, BioUltra) and phosphodiesterase I from Crotalus adamanteus venom (0.0055 units, Sigma-Aldrich, Purified) for 18 h at 37 C. The enzyme caused partial deamination of dA to dI (confirmed in model experiment).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6098 - 6106

60
C₉₉H₁₂₄FN₃₆O₅₈P₉S [ No CAS ]
[ 890-38-0 ]
[ 869355-51-1 ]
[ 961-07-9 ]
[ 951-77-9 ]
[ 50-89-5 ]
[ 958-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Crotalus adamanteus venom phosphodiesterase I; bovine intestinal mucosa alkaline phosphatase; water; magnesium chloride; at 37℃; for 18h;pH 7.0;aq. phosphate buffer; Enzymatic reaction;	General procedure: Column containing solid support with the synthesized oligonucleotide was attached to a syringe containing 2 mL of 0.4 M solution of DBU in anhydr CH3CN. Approx. 0.7 mL of the solution was pushed into the column, replaced by a new portion after 5 min and another one after next 5 min. After total time of 15 min the support was washed with dry CH3CN (10 mL) and dried in vacuo. The dried support was placed into a vial, 1 mL of approx. 22% methanolic ammonia was added and the vial closed tightly. After 3 h at rt the solid was filtered off, washed with methanol and water and the filtrates were evaporated. The residue was dissolved in 0.1 m ammonium acetate (1 mL) and passed through a NAP 25 column. The column was washed with the same solution and 6 fractions of 1.4 mL were collected and checked by UV. The oligomer was present mainly in the fractions 3 and 4, with some residue in 5th fraction. Combined fractions were evaporated, dissolved in H2O/acetonitrile, 95/5, v/v (1 mL) and purified by HPLC (two 500 mul injections, Waters XBridge OST C18 Column, 2.5 mum,10 × 50 mm, phase A = 0.1 M TEAA, B = 0.1 M TEAA/Acetonitrile, 50/50, v/v, flow rate 1 ml/min, T = 40 C, gradient 17-20%B in 10 min, then to 50%B in 5 min. Combined fractions were concentrated to approx. 0.5 mL and desalted by passage through HPLC column. Yields of the oligomers BS3-BS6 see Table 1. The oligomerswere verified by enzymatic digestion, results see Table 3. Enzymatic digestion conditions: 0.2 OD of oligonucleotide in 150 muL of buffer (10 mM KH2PO4, 10 mM MgCl2, pH 7) was digested with alkaline phosphatase bovine intestinal mucosa (27 DEA units, Sigma-Aldrich, BioUltra) and phosphodiesterase I from Crotalus adamanteus venom (0.0055 units, Sigma-Aldrich, Purified) for 18 h at 37 C. The enzyme caused partial deamination of dA to dI (confirmed in model experiment).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6098 - 6106

61
C₉₈H₁₂₂FN₄₀O₅₆P₉S [ No CAS ]
[ 890-38-0 ]
[ 869355-51-1 ]
[ 961-07-9 ]
[ 951-77-9 ]
[ 50-89-5 ]
[ 958-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Crotalus adamanteus venom phosphodiesterase I; bovine intestinal mucosa alkaline phosphatase; water; magnesium chloride; at 37℃; for 18h;pH 7.0;aq. phosphate buffer; Enzymatic reaction;	General procedure: Column containing solid support with the synthesized oligonucleotide was attached to a syringe containing 2 mL of 0.4 M solution of DBU in anhydr CH3CN. Approx. 0.7 mL of the solution was pushed into the column, replaced by a new portion after 5 min and another one after next 5 min. After total time of 15 min the support was washed with dry CH3CN (10 mL) and dried in vacuo. The dried support was placed into a vial, 1 mL of approx. 22% methanolic ammonia was added and the vial closed tightly. After 3 h at rt the solid was filtered off, washed with methanol and water and the filtrates were evaporated. The residue was dissolved in 0.1 m ammonium acetate (1 mL) and passed through a NAP 25 column. The column was washed with the same solution and 6 fractions of 1.4 mL were collected and checked by UV. The oligomer was present mainly in the fractions 3 and 4, with some residue in 5th fraction. Combined fractions were evaporated, dissolved in H2O/acetonitrile, 95/5, v/v (1 mL) and purified by HPLC (two 500 mul injections, Waters XBridge OST C18 Column, 2.5 mum,10 × 50 mm, phase A = 0.1 M TEAA, B = 0.1 M TEAA/Acetonitrile, 50/50, v/v, flow rate 1 ml/min, T = 40 C, gradient 17-20%B in 10 min, then to 50%B in 5 min. Combined fractions were concentrated to approx. 0.5 mL and desalted by passage through HPLC column. Yields of the oligomers BS3-BS6 see Table 1. The oligomerswere verified by enzymatic digestion, results see Table 3. Enzymatic digestion conditions: 0.2 OD of oligonucleotide in 150 muL of buffer (10 mM KH2PO4, 10 mM MgCl2, pH 7) was digested with alkaline phosphatase bovine intestinal mucosa (27 DEA units, Sigma-Aldrich, BioUltra) and phosphodiesterase I from Crotalus adamanteus venom (0.0055 units, Sigma-Aldrich, Purified) for 18 h at 37 C. The enzyme caused partial deamination of dA to dI (confirmed in model experiment).

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6098 - 6106

62
[ 1123-54-2 ]
[ 951-77-9 ]
8-Aza-2'-deoxy-adenosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With purine nucleoside phosphorylase In dimethyl sulfoxide at 50℃; for 72h; aq. phosphate buffer; Enzymatic reaction;

Reference： [1]Location in patent: experimental part Stepchenko, Vladimir A.; Seela, Frank; Esipov, Roman S.; Miroshnikov, Anatoly I.; Sokolov, Yuri A.; Mikhailopulo, Igor A. [Synlett, 2012, vol. 23, # 10, p. 1541 - 1545]

63
5'-d(CAGCTPMeG), PMe = methylphosphonate link [ No CAS ]
5'-d(pTPMeG), PMe = methylphosphonate link [ No CAS ]
[ 1032-65-1 ]
[ 653-63-4 ]
[ 902-04-5 ]
[ 951-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	With nuclease P₁ from Penicillium citrinum at 37℃; for 0.0833333h; Enzymatic reaction;

Reference： [1]Tomaszewska, Agnieszka; Mourgues, Sophie; Guga, Piotr; Nawrot, Barbara; Pratviel, Genevieve [Chemical Research in Toxicology, 2012, vol. 25, # 11, p. 2505 - 2512]

64
[ 838-07-3 ]
[ 951-77-9 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 14593 - 14599
[2]Journal of the American Chemical Society,2013,vol. 135,p. 14593 - 14599

65
[ 544-35-4 ]
[ 951-77-9 ]
[ 566943-69-9 ]
[ 1461733-59-4 ]
C₁₇H₂₅N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethyl (9Z,12Z)-9,12-octadecadienoate; 2'-Deoxycytidine With iron(III) protoporphyrin IX chloride In aq. phosphate buffer at 20℃; for 72h; Stage #2: In aq. phosphate buffer; acetonitrile for 456h; Sealed tube;

Reference： [1]Kawai, Kazuaki; Kawasaki, Yuya; Kubota, Yumiko; Kimura, Tomoyuki; Sawa, Ryuichi; Matsuda, Tomonari; Kasai, Hiroshi [Chemical Research in Toxicology, 2013, vol. 26, # 10, p. 1554 - 1560]

66
{5'-d(ATGGGC[¹⁵N_3,¹³_C₁-2'-G]GCATGAAC)-3'}*{3'-d(TACCCGCCGTACAAG)-5'} [ No CAS ]
[ 137608-88-9 ]
[ 88847-89-6 ]
2'-deoxyadenosine [ No CAS ]
[ 951-77-9 ]
[ 50-89-5 ]