[ CAS No. 146954-75-8 ] {[proInfo.proName]}

Name: 146954-75-8|(2R,3R,4R,5R)-2-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluorotetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite|95%
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SKU: A107605
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Quality Control of [ 146954-75-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 146954-75-8 ]

SDS Specification

Alternatived Products of [ 146954-75-8 ]

Product Details of [ 146954-75-8 ]

CAS No. :	146954-75-8	MDL No. :	MFCD11113919
Formula :	C₃₉H₄₆FN₄O₈P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HQHQPAYRJJMYQX-DJTPZYMWSA-N
M.W :	748.78	Pubchem ID :	9810693
Synonyms :	2'-F-dU Phosphoramidite	Chemical Name :	(2R,3R,4R,5R)-2-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluorotetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite

Calculated chemistry of [ 146954-75-8 ]

Physicochemical Properties

Num. heavy atoms :	53
Num. arom. heavy atoms :	24
Fraction Csp3 :	0.41
Num. rotatable bonds :	17
Num. H-bond acceptors :	11.0
Num. H-bond donors :	1.0
Molar Refractivity :	199.11
TPSA :	150.86 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-7.08 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.97
Log Po/w (XLOGP3) :	5.33
Log Po/w (WLOGP) :	6.45
Log Po/w (MLOGP) :	1.95
Log Po/w (SILICOS-IT) :	5.96
Consensus Log Po/w :	4.93

Druglikeness

Lipinski :	2.0
Ghose :	None
Veber :	2.0
Egan :	2.0
Muegge :	5.0
Bioavailability Score :	0.17

Water Solubility

Log S (ESOL) :	-7.05
Solubility :	0.0000662 mg/ml ; 0.0000000884 mol/l
Class :	Poorly soluble
Log S (Ali) :	-8.25
Solubility :	0.00000421 mg/ml ; 0.0000000056 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-9.8
Solubility :	0.000000119 mg/ml ; 0.0000000002 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	6.96

Safety of [ 146954-75-8 ]

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

Application In Synthesis of [ 146954-75-8 ]

* 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 [ 146954-75-8 ]
Downstream synthetic route of [ 146954-75-8 ]

[ 146954-75-8 ] Synthesis Path-Upstream 1~6

1
[ 102691-36-1 ]
[ 146954-74-7 ]
[ 146954-75-8 ]

Yield	Reaction Conditions	Operation in experiment
67.3%	With 1H-tetrazole; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere	5’-O-(4,4’-Dimethoxytrityl)-2’-deoxy-2’-fluorouridine (3.00 g, 5.47 mmol) obtained in Preparation Example 27-(1)was dissolved in anhydrous dichloromethane (50 ml) under an argon atmosphere, N,N-diisopropylethylamine (0.55 ml,3.18 mmol), 1H-tetrazole (0.45 g, 6.45 mmol) and 2-cyanoethyl-N,N,N’,N’-tetraisopropylphosphordiamidite (1.92 g, 6.36mmol) were added, and the mixture was stirred at room temperature overnight. The completion of the reaction wasconfirmed, 5percent aqueous sodium hydrogen carbonate solution (20 ml) was added to the reaction mixture to allow layerseparation, and the organic layer was washed with saturated brine (20 ml). The organic layer was dried over sodiumsulfate, the filtrate was concentrated and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=75:25 - 30/70(v/v), containing 3percent triethylamine). The object fractions were collected and concentratedto give the title compound (2.76 g, 67.3percent).

Reference： [1] Patent: EP2816053, 2014, A1, . Location in patent: Paragraph 0371
[2] Patent: US9371353, 2016, B2, . Location in patent: Page/Page column 78

2
[ 146954-74-7 ]
[ 146954-75-8 ]

Reference： [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 7, p. 831 - 841

3
[ 124482-92-4 ]
[ 146954-74-7 ]
[ 146954-75-8 ]

Reference： [1] Helvetica Chimica Acta, 1997, vol. 80, # 6, p. 1952 - 1971

4
[ 40615-36-9 ]
[ 146954-75-8 ]

Reference： [1] Helvetica Chimica Acta, 1997, vol. 80, # 6, p. 1952 - 1971
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 7, p. 831 - 841

5
[ 56287-17-3 ]
[ 146954-75-8 ]

Reference： [1] Helvetica Chimica Acta, 1997, vol. 80, # 6, p. 1952 - 1971
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 7, p. 831 - 841

6
[ 40615-36-9 ]
[ 56287-17-3 ]
[ 146954-75-8 ]

Reference： [1] Patent: EP2816053, 2014, A1,
[2] Patent: US9371353, 2016, B2,

[ 146954-75-8 ] Synthesis Path-Downstream 1~16

1
2-(Cyanethoxy)-bis-N,N-(diisopropylamino)phosphane [ No CAS ]
[ 146954-74-7 ]
[ 146954-75-8 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 831 - 841

2
[ 288-88-0 ]
[ 146954-75-8 ]
5'-O-dimethoxytrityl-2'-fluoro-2'-deoxy-N⁴-1,2,4-triazolouridine-3'-O-(O-cyanoethyl-N,N-diisopropylamino)phosphite [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1791 - 1796

3
[ 124482-92-4 ]
[ 146954-74-7 ]
[ 146954-75-8 ]

Reference： [1]Helvetica Chimica Acta,1997,vol. 80,p. 1952 - 1971

4
[ 146954-75-8 ]
[ 161442-19-9 ]
protected guanosine [ No CAS ]
C₉₄H₁₁₄F₆N₃₆O₆₇P₁₀ [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1997,vol. 80,p. 1952 - 1971

5
[ 40615-36-9 ]
[ 146954-75-8 ]

Reference： [1]Helvetica Chimica Acta,1997,vol. 80,p. 1952 - 1971
[2]Journal of Medicinal Chemistry,1993,vol. 36,p. 831 - 841

6
[ 56287-17-3 ]
[ 146954-75-8 ]

Reference： [1]Helvetica Chimica Acta,1997,vol. 80,p. 1952 - 1971
[2]Journal of Medicinal Chemistry,1993,vol. 36,p. 831 - 841

Yield	Reaction Conditions	Operation in experiment
67.3%	With triethylamine;	The organic layer was dried over sodium sulfate, the filtrate was concentrated and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=75:25-30/70 (v/v), containing 3% triethylamine). The object fractions were collected and concentrated to give the title compound (2.76 g, 67.3%).
		2'-Fluorouridine Synthesis of 2'-deoxy-2'-fluorouridine was accomplished by the modification of a literature procedure in which 2,2'-anhydro-1-beta-D-arabinofuranosyluracil was treated with 70% hydrogen fluoride-pyridine. Standard procedures were used to obtain the 5'-DMT and 5'-DMT-3'phosphoramidites.

8
[ 40615-36-9 ]
[ 56287-17-3 ]
[ 146954-75-8 ]

Reference： [1]Patent: EP2816053,2014,A1
[2]Patent: US9371353,2016,B2

9
[ 102691-36-1 ]
[ 146954-74-7 ]
[ 146954-75-8 ]

Yield	Reaction Conditions	Operation in experiment
67.3%	With 1H-tetrazole; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Inert atmosphere;	5?-O-(4,4?-Dimethoxytrityl)-2?-deoxy-2?-fluorouridine (3.00 g, 5.47 mmol) obtained in Preparation Example 27-(1)was dissolved in anhydrous dichloromethane (50 ml) under an argon atmosphere, N,N-diisopropylethylamine (0.55 ml,3.18 mmol), 1H-tetrazole (0.45 g, 6.45 mmol) and 2-cyanoethyl-N,N,N?,N?-tetraisopropylphosphordiamidite (1.92 g, 6.36mmol) were added, and the mixture was stirred at room temperature overnight. The completion of the reaction wasconfirmed, 5% aqueous sodium hydrogen carbonate solution (20 ml) was added to the reaction mixture to allow layerseparation, and the organic layer was washed with saturated brine (20 ml). The organic layer was dried over sodiumsulfate, the filtrate was concentrated and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=75:25 - 30/70(v/v), containing 3% triethylamine). The object fractions were collected and concentratedto give the title compound (2.76 g, 67.3%).
67.3%	With triethylamine;	5?-O-(4,4?-Dimethoxytrityl)-2?-deoxy-2?-fluorouridine (3.00 g, 5.47 mmol) obtained in Preparation Example 27-(1) was dissolved in anhydrous dichloromethane (50 ml) under an argon atmosphere, N,N-diisopropylethylamine (0.55 ml, 3.18 mmol), 1H-tetrazole (0.45 g, 6.45 mmol) and 2-cyanoethyl-N,N,N?,N?-tetraisopropylphosphordiamidite (1.92 g, 6.36 mmol) were added, and the mixture was stirred at room temperature overnight. The completion of the reaction was confirmed, 5% aqueous sodium hydrogen carbonate solution (20 ml) was added to the reaction mixture to allow layer separation, and the organic layer was washed with saturated brine (20 ml). The organic layer was dried over sodium sulfate, the filtrate was concentrated and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=75:25-30/70 (v/v), containing 3% triethylamine). The object fractions were collected and concentrated to give the title compound (2.76 g, 67.3%).

Reference： [1]Patent: EP2816053,2014,A1 .Location in patent: Paragraph 0371
[2]Patent: US9371353,2016,B2 .Location in patent: Page/Page column 78

10
octadecanedioic acid mono-triisopropylsilyl ester [ No CAS ]
(2R,3R,4R,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl(2-cyanoethyl)diisopropylphosphoramidite [ No CAS ]
[ 98796-51-1 ]
[ 146954-75-8 ]
[ 253586-13-9 ]
[ 253586-14-0 ]
3'-fluorescein-dT-CPG [ No CAS ]
5'-(HOOC-(CH2)16-CONH-(CH2)2-O-(CH2)2-OPO2H-GGACFCFACFCFGCFAUFCFUFCFUFACFAdTdTFAM)-3', 2'F-pyrimidine is indicated by a superscript F in the oligonucleotide sequence [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Oligonucleotides were synthesized on an ABI 394 DNA/RNA synthesizer (Applied Biosystems) in synthesis columns loaded with 1 muetaiotaomicronbeta CPG (1000 A pore size, Glen Research) bearing the first 5'-Dmt-protected nucleotide. All cyanoethyl phosphoramidites (CEP As) were purchased from Glen Research: Dmt-dT-CEPA (10-1030) for DNA nucleotides, Dmt-AAc-TOM-CEPA (10-3004), Dmt-GAc-TOM-CEPA for RNA nucleotides, and Dmt-2'F-CAc-CEPA (10-3415) and Dmt-2'F-U-CEPA (10-3430) for 2'F-RNA nucleotides (the presence of a 2'F-pyrimidine is indicated by a superscript F in the oligonucleotide sequence). 5'-Amino-modifier-5 (10-1905) was used to install a terminal amine on the passenger strand. 3'-Fluorescein-labeled sequences were synthesized on 3'- fluorescein-dT-CPG (20-2056). 4,5-Dicyanoimidazole (DCC) and 5-(benzylthio)-lH- tetrazole (BTT) were used as activators for the synthesis of DNA and RNA/2'F-RNA, respectively. Capping was performed with THF/pyridine/acetic anhydride in acetonitrile (Cap Mix A) and 16% 1 -methyl imidazole in THF (Cap Mix B). In each cycle, the phosphorus was oxidized by treatment with 0.02 M iodine in THF/pyridine/water. All 5 ' -trity 1 protecting groups were cleaved with 3% trichloroacetic acid in DCM. A coupling cycle consisted of the following steps: detritylation, coupling, capping, and oxidation. Detritylation times were 60 s, coupling times were 30 s for DNA and the 5'-amino-modifier and 180 s for RNA/2'F-RNA. Capping was performed for 5 s, oxidation was carried out for 15 s. All washing and reagent delivery steps were performed as given in the instrument's default synthesis cycle. Conjugation of octadecanedioic acid (ODDA) to the 5'-terminus of amine-modified nucleic acids Before coupling, the terminal Mmt protecting group of the 5'-aminomodifier was cleaved by flushing the support-bound fully protected nucleic acid with 3% trichloroacetic acid in DCM until the yellow color of the Mmt-cation was no longer observable by eye (ca. 3-4.5 min). The support was washed with DCM and acetonitrile and briefly dried under an argon stream. Residual solvent was removed in a desiccator Conjugation with small molecules: A solution of 10 equiv. of ODDA-mono-triisopropylsilyl ester (ODDA-TIPS), 9 equiv. HATU and 30 equiv. DIPEA in anhydrous DMF was pre- activated for 5 min and subsequently added to the dried support bearing the 5'- aminomodified nucleic acid sequence. The synthesis column was shaken for 2 h, the support was washed with NMP and DCM and dried in vacuo. The coupling reaction was repeated once with fresh activated ODDA-TIPS (2 h). The support was washed extensively with NMP and DCM to flush away unreacted carboxylic acids and dried in vacuo. The support was stored in a desiccator until the conjugate was cleaved and deprotected. Release from the solid support and deprotection of nucleic acid conjugates Release of the CPG-bound oligonucleotides and deprotection of the nucleobases as well as removal of the cyanoethyl protecting groups was carried out by immersing the support in AMA (30% ammonium hydroxide, 40% aqueous methylamine, 1 : 1, v.v). If a pivaloyl- protected fluorescein dye was present in the sequence, the support was first treated with 30% ammonium hydroxide for 1 h at room temperature to remove the pivaloyl protecting groups before an equal volume of 40% aqueous methylamine was added. AMA solutions containing the solid supports were incubated for 2 h at room temperature to finish deprotection. After centrifugation, the supernatant was removed and the support was washed with 4* 200 water. The combined solutions were dried down under a stream of dinitrogen (heat should be avoided if 2'F-RNA nucleotides are present in the sequence). To remove 2'TOM protecting groups, the residue was re-dissolved in 115 anhydrous DMSO (5 min 65 C) and 60 of anhydrous triethylamine were added. 75 triethylamine hydrofluoride complex (NEt3 x 3 HF) were added, and the solution was incubated for 2.5 h at 65 C. Afterwards, the solution was briefly cooled in a freezer, and 25 mu of 3 M sodium acetate were added. The oligonucleotide was precipitated with 1 mL of butanol, and incubated for 30 min at -20 C. The suspension was centrifuged for 10 min (12000 rcf) and the supernatant was removed. The precipitate was washed with 2* 750 mu ethanol and briefly dried by vacuum centrifugation. The crude oligonucleotide was dissolved in water and analyzed by analytical HPLC and purified by semi-preparative HPLC. The product containing fractions were reduced to < 10 mL by vacuum centrifugation and the oligonucleotide was desalted using Sep-Pak C-18 cartridges (Waters). The cartridges were washed with 10 mL acetonitrile and equilibrated with 10 mL water. The oligonucleotides were loaded, washed with 10 mL water, eluted with ca. 6 mL water: acetonitrile (1 : 1, v.v), dried under reduced pressure and re- dissolved in water. Concentrations were determined via UV-vis spectroscopy and product identity and purity was verified ...

Reference： [1]Patent: WO2018/175592,2018,A1 .Location in patent: Page/Page column 27-30

11
octadecanedioic acid mono-triisopropylsilyl ester [ No CAS ]
(2R,3R,4R,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl(2-cyanoethyl)diisopropylphosphoramidite [ No CAS ]
[ 98796-51-1 ]
[ 146954-75-8 ]
[ 253586-13-9 ]
[ 253586-14-0 ]
dT-CPG [ No CAS ]
5'-(HOOC-(CH2)16-CONH-(CH2)2-O-(CH2)2-OPO2H-GGACFCFACFCFGCFAUFCFUFCFUFACFAdTdT)-3', 2'F-pyrimidine is indicated by a superscript F in the oligonucleotide sequence [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Oligonucleotides were synthesized on an ABI 394 DNA/RNA synthesizer (Applied Biosystems) in synthesis columns loaded with 1 muetaiotaomicronbeta CPG (1000 A pore size, Glen Research) bearing the first 5'-Dmt-protected nucleotide. All cyanoethyl phosphoramidites (CEP As) were purchased from Glen Research: Dmt-dT-CEPA (10-1030) for DNA nucleotides, Dmt-AAc-TOM-CEPA (10-3004), Dmt-GAc-TOM-CEPA for RNA nucleotides, and Dmt-2'F-CAc-CEPA (10-3415) and Dmt-2'F-U-CEPA (10-3430) for 2'F-RNA nucleotides (the presence of a 2'F-pyrimidine is indicated by a superscript F in the oligonucleotide sequence). 5'-Amino-modifier-5 (10-1905) was used to install a terminal amine on the passenger strand. 3'-Fluorescein-labeled sequences were synthesized on 3'- fluorescein-dT-CPG (20-2056). 4,5-Dicyanoimidazole (DCC) and 5-(benzylthio)-lH- tetrazole (BTT) were used as activators for the synthesis of DNA and RNA/2'F-RNA, respectively. Capping was performed with THF/pyridine/acetic anhydride in acetonitrile (Cap Mix A) and 16% 1 -methyl imidazole in THF (Cap Mix B). In each cycle, the phosphorus was oxidized by treatment with 0.02 M iodine in THF/pyridine/water. All 5 ' -trity 1 protecting groups were cleaved with 3% trichloroacetic acid in DCM. A coupling cycle consisted of the following steps: detritylation, coupling, capping, and oxidation. Detritylation times were 60 s, coupling times were 30 s for DNA and the 5'-amino-modifier and 180 s for RNA/2'F-RNA. Capping was performed for 5 s, oxidation was carried out for 15 s. All washing and reagent delivery steps were performed as given in the instrument's default synthesis cycle. Conjugation of octadecanedioic acid (ODDA) to the 5'-terminus of amine-modified nucleic acids Before coupling, the terminal Mmt protecting group of the 5'-aminomodifier was cleaved by flushing the support-bound fully protected nucleic acid with 3% trichloroacetic acid in DCM until the yellow color of the Mmt-cation was no longer observable by eye (ca. 3-4.5 min). The support was washed with DCM and acetonitrile and briefly dried under an argon stream. Residual solvent was removed in a desiccator Conjugation with small molecules: A solution of 10 equiv. of ODDA-mono-triisopropylsilyl ester (ODDA-TIPS), 9 equiv. HATU and 30 equiv. DIPEA in anhydrous DMF was pre- activated for 5 min and subsequently added to the dried support bearing the 5'- aminomodified nucleic acid sequence. The synthesis column was shaken for 2 h, the support was washed with NMP and DCM and dried in vacuo. The coupling reaction was repeated once with fresh activated ODDA-TIPS (2 h). The support was washed extensively with NMP and DCM to flush away unreacted carboxylic acids and dried in vacuo. The support was stored in a desiccator until the conjugate was cleaved and deprotected. Release from the solid support and deprotection of nucleic acid conjugates Release of the CPG-bound oligonucleotides and deprotection of the nucleobases as well as removal of the cyanoethyl protecting groups was carried out by immersing the support in AMA (30% ammonium hydroxide, 40% aqueous methylamine, 1 : 1, v.v). If a pivaloyl- protected fluorescein dye was present in the sequence, the support was first treated with 30% ammonium hydroxide for 1 h at room temperature to remove the pivaloyl protecting groups before an equal volume of 40% aqueous methylamine was added. AMA solutions containing the solid supports were incubated for 2 h at room temperature to finish deprotection. After centrifugation, the supernatant was removed and the support was washed with 4* 200 water. The combined solutions were dried down under a stream of dinitrogen (heat should be avoided if 2'F-RNA nucleotides are present in the sequence). To remove 2'TOM protecting groups, the residue was re-dissolved in 115 anhydrous DMSO (5 min 65 C) and 60 of anhydrous triethylamine were added. 75 triethylamine hydrofluoride complex (NEt3 x 3 HF) were added, and the solution was incubated for 2.5 h at 65 C. Afterwards, the solution was briefly cooled in a freezer, and 25 mu of 3 M sodium acetate were added. The oligonucleotide was precipitated with 1 mL of butanol, and incubated for 30 min at -20 C. The suspension was centrifuged for 10 min (12000 rcf) and the supernatant was removed. The precipitate was washed with 2* 750 mu ethanol and briefly dried by vacuum centrifugation. The crude oligonucleotide was dissolved in water and analyzed by analytical HPLC and purified by semi-preparative HPLC. The product containing fractions were reduced to < 10 mL by vacuum centrifugation and the oligonucleotide was desalted using Sep-Pak C-18 cartridges (Waters). The cartridges were washed with 10 mL acetonitrile and equilibrated with 10 mL water. The oligonucleotides were loaded, washed with 10 mL water, eluted with ca. 6 mL water: acetonitrile (1 : 1, v.v), dried under reduced pressure and re- dissolved in water. Concentrations were determined via UV-vis spectroscopy and product identity and purity was verified ...

Reference： [1]Patent: WO2018/175592,2018,A1 .Location in patent: Page/Page column 27-31

12
(2R,3R,4R,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl(2-cyanoethyl)diisopropylphosphoramidite [ No CAS ]
[ 98796-51-1 ]
[ 146954-75-8 ]
[ 253586-13-9 ]
[ 253586-14-0 ]
dT-CPG [ No CAS ]
5'-(UFGUFAGAGAUFGCFGGUFGGUFCFCFdTdT)-3', 2'F-pyrimidine is indicated by a superscript F in the oligonucleotide sequence [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Oligonucleotides were synthesized on an ABI 394 DNA/RNA synthesizer (Applied Biosystems) in synthesis columns loaded with 1 muetaiotaomicronbeta CPG (1000 A pore size, Glen Research) bearing the first 5'-Dmt-protected nucleotide. All cyanoethyl phosphoramidites (CEP As) were purchased from Glen Research: Dmt-dT-CEPA (10-1030) for DNA nucleotides, Dmt-AAc-TOM-CEPA (10-3004), Dmt-GAc-TOM-CEPA for RNA nucleotides, and Dmt-2'F-CAc-CEPA (10-3415) and Dmt-2'F-U-CEPA (10-3430) for 2'F-RNA nucleotides (the presence of a 2'F-pyrimidine is indicated by a superscript F in the oligonucleotide sequence). 5'-Amino-modifier-5 (10-1905) was used to install a terminal amine on the passenger strand. 3'-Fluorescein-labeled sequences were synthesized on 3'- fluorescein-dT-CPG (20-2056). 4,5-Dicyanoimidazole (DCC) and 5-(benzylthio)-lH- tetrazole (BTT) were used as activators for the synthesis of DNA and RNA/2'F-RNA, respectively. Capping was performed with THF/pyridine/acetic anhydride in acetonitrile (Cap Mix A) and 16% 1 -methyl imidazole in THF (Cap Mix B). In each cycle, the phosphorus was oxidized by treatment with 0.02 M iodine in THF/pyridine/water. All 5 ' -trity 1 protecting groups were cleaved with 3% trichloroacetic acid in DCM. A coupling cycle consisted of the following steps: detritylation, coupling, capping, and oxidation. Detritylation times were 60 s, coupling times were 30 s for DNA and the 5'-amino-modifier and 180 s for RNA/2'F-RNA. Capping was performed for 5 s, oxidation was carried out for 15 s. All washing and reagent delivery steps were performed as given in the instrument's default synthesis cycle. Conjugation of octadecanedioic acid (ODDA) to the 5'-terminus of amine-modified nucleic acids Before coupling, the terminal Mmt protecting group of the 5'-aminomodifier was cleaved by flushing the support-bound fully protected nucleic acid with 3% trichloroacetic acid in DCM until the yellow color of the Mmt-cation was no longer observable by eye (ca. 3-4.5 min). The support was washed with DCM and acetonitrile and briefly dried under an argon stream. Residual solvent was removed in a desiccator Conjugation with small molecules: A solution of 10 equiv. of ODDA-mono-triisopropylsilyl ester (ODDA-TIPS), 9 equiv. HATU and 30 equiv. DIPEA in anhydrous DMF was pre- activated for 5 min and subsequently added to the dried support bearing the 5'- aminomodified nucleic acid sequence. The synthesis column was shaken for 2 h, the support was washed with NMP and DCM and dried in vacuo. The coupling reaction was repeated once with fresh activated ODDA-TIPS (2 h). The support was washed extensively with NMP and DCM to flush away unreacted carboxylic acids and dried in vacuo. The support was stored in a desiccator until the conjugate was cleaved and deprotected. Release from the solid support and deprotection of nucleic acid conjugates Release of the CPG-bound oligonucleotides and deprotection of the nucleobases as well as removal of the cyanoethyl protecting groups was carried out by immersing the support in AMA (30% ammonium hydroxide, 40% aqueous methylamine, 1 : 1, v.v). If a pivaloyl- protected fluorescein dye was present in the sequence, the support was first treated with 30% ammonium hydroxide for 1 h at room temperature to remove the pivaloyl protecting groups before an equal volume of 40% aqueous methylamine was added. AMA solutions containing the solid supports were incubated for 2 h at room temperature to finish deprotection. After centrifugation, the supernatant was removed and the support was washed with 4* 200 water. The combined solutions were dried down under a stream of dinitrogen (heat should be avoided if 2'F-RNA nucleotides are present in the sequence). To remove 2'TOM protecting groups, the residue was re-dissolved in 115 anhydrous DMSO (5 min 65 C) and 60 of anhydrous triethylamine were added. 75 triethylamine hydrofluoride complex (NEt3 x 3 HF) were added, and the solution was incubated for 2.5 h at 65 C. Afterwards, the solution was briefly cooled in a freezer, and 25 mu of 3 M sodium acetate were added. The oligonucleotide was precipitated with 1 mL of butanol, and incubated for 30 min at -20 C. The suspension was centrifuged for 10 min (12000 rcf) and the supernatant was removed. The precipitate was washed with 2* 750 mu ethanol and briefly dried by vacuum centrifugation. The crude oligonucleotide was dissolved in water and analyzed by analytical HPLC and purified by semi-preparative HPLC. The product containing fractions were reduced to < 10 mL by vacuum centrifugation and the oligonucleotide was desalted using Sep-Pak C-18 cartridges (Waters). The cartridges were washed with 10 mL acetonitrile and equilibrated with 10 mL water. The oligonucleotides were loaded, washed with 10 mL water, eluted with ca. 6 mL water: acetonitrile (1 : 1, v.v), dried under reduced pressure and re- dissolved in water. Concentrations were determined via UV-vis spectroscopy and product identity and purity was verified ...

Reference： [1]Patent: WO2018/175592,2018,A1 .Location in patent: Page/Page column 27-31

13
[ 1427269-36-0 ]
[ 146954-75-8 ]
C₃₅H₃₇F₂N₉O₁₃P₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3H-1,2-Benzodithiol-3-one 1,1-dioxide; 5-(ethylthio)-1H-tetrazole; In acetonitrile;	A and B were treated with 5-(ethylthio)-lH-tetrazole in acetonitrile and the Iyer- aucage reagent. Following this, the product was detritlyated to yield C. C was then treated with sodium iodide in acetone to yield deprotected product D. D was treated with 1-mesitylene-2-sulfonyl-3-nitro-l,2,4-triazole and pyridine to yield cyclized product E.

Reference： [1]Patent: WO2019/51488,2019,A1 .Location in patent: Page/Page column 107; 108

14
(2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl 4-oxopentanoate [ No CAS ]
[ 146954-75-8 ]
C₅₅H₅₃F₂N₈O₁₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 5-(ethylthio)-1H-tetrazole; In acetonitrile; at 20℃; for 2h;Inert atmosphere;	5'OH-3'-Levulinylated-2'F-deoxy-Adinosine (700 mg, 1.48 mmol) and 5'DMT-2'F-3'CED-Phosphoamidite-deoxy-Uridine (1.66 g, 2.22 mmol) mixture was dried under high vacuum for 1-2 hours. Argon was flushed over the round bottom flask containing reaction mixture. Anhydrous acetonitrile (40 mL) was added to reaction mixture Followed by ETT (279 mg, 2.146 mmol) in acetonitrile (5.0 mL) under atmosphere of argon. The resulting mixture was stirred at room temperature under argon for 2 h. Once TLC analysis showed reaction completion, water was added (80 mu, 2 equivalents to amidite).

Reference： [1]Patent: WO2019/51489,2019,A1 .Location in patent: Page/Page column 106-108

15
[ 171268-84-1 ]
[ 146954-75-8 ]
C₄₉H₅₉FN₅O₁₄PSSi [ No CAS ]
C₄₉H₅₉FN₅O₁₄PSSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Compound 17: Compound 15 (11.01 g, 14.7 mmol) and compound 16 (5.74 g, 15.4 mmol, 1.05 eq.) were dried under high vacuum and dissolved in 100 ml dichloromethane (dry). To the solution was added 117 ml ETT (3.83 g, 29.4 mmol, 2 eq.), and the reaction mixture was stirred for 2.5 hours. PADS (6.35 g, 22.05 mmol, 1.5 eq.) and 2.52 ml 2.6-lutidine (2.36 g, 22.05 mmol, 1.5 eq.) were added, and the reaction mixture was stirred overnight. The reaction mixture was diluted with 800 ml dichloromethane and washed with 0 (300 ml) twice. The organic layer was dried over anhydrous Na2SO i and concentrated. The diastereomers were separated over CombiFlash column (330 g column, EtOAc: n-hexane (4: 1)) to yield 17a (top spot: 7.25 g 47%) and 17b (lower spot: 7.29 g, 47%)). In EtOAc: n- hexane (4: 1), 17a Rf = 0.23 and 17b Rf = 0.18. (0825) 17a NMR (400 MHz, DMS0 ) d 11.43 (s, 1H), 11.33 (s, 1H), 7.77 (d, J= 8.0 Hz, 1H), 7.57 (d, J= 8.1 Hz, 1H), 7.42 - 7.36 (m, 2H), 7.33 - 7.20 (m, 7H), 6.91 - 6.84 (m, 4H), 5.92 (d, J= 21.4 Hz, 1H), 5.81 (d, = 4.5 Hz, 1H), 5.63 (dd, .7= 8.1, 1.8 Hz, 1H), 5.60 - 5.42 (m, 2H), 5.36 - 5.24 (m, 1H), 4.34 - 4.21 (m, 3H), 4.21 - 4.06 (m, 2H), 4.03 - 3.93 (m, 2H), 3.86 (t, J= 4.8 Hz, 1H), 3.73 (s, 6H), 3.38 (d , J= 9.5 Hz, 1H), 3.34 (s, 3H), 3.29 (dd, J= 11.0, 4.8 Hz, 1H), 2.83 - 2.73 (m, 2H), 0.87 (s, 9H), 0.08 (s, 5H). 13C NMR (126 MHz, DMSO) d (0826) 163.11, 162.92, 158.13, 158.11, 150.31, 150.02, 144.31, 142.07, 140.13, 135.08, 135.03, 129.77, 129.72, 127.81, 127.76, 126.78, 120.26, 117.70, 113.15, 102.12, 101.73, 91.63, (0827) 90.05, 90.03, 89.75, 87.12, 85.97, 81.69, 81.62, 81.24, 79.61, 79.54, 73.12, 73.01, 69.64, 67.08, 67.06, 63.26, 63.23, 61.58, 57.61, 55.00, 25.54, 18.77, 18.70, 17.68, -4.88, -5.14. 31P NMR (202 MHz, DMSO) d 68.19. 19F NMR (376 MHz, DMSO) d -203.64, -203.70, -203.75, -203.78, -203.83, -203.89. Molecular weight for C49H59FN5O14PSS1 (M+Na): calculated 1074.368, found 1074.3170. (0828) 17b NMR (400 MHz, DMSO-ufe) d 11.51 - 11.46 (m, 1H), 11.43 - 11.38 (m, 1H), 7.80 (d, J= 8.1 Hz, 1H), 7.56 (d, j= 8.2 Hz, 1H), 7.38 (d, J= 7.5 Hz, 2H), 7.31 - 7.20 (m, 7H), 6.85 (dd, J= 8.9, 2.1 Hz, 4H), 5.91 (d, j= 21.8 Hz, 1H), 5.78 (d, J= 4.0 Hz, 1H), 5.63 - 5.46 (m, 2H), 5.41 (dd, J= 8.0, 2.0 Hz, 1H), 5.38 - 5.25 (m, 1H), 4.27 - 4.15 (m, 4H), 4.15 - 4.06 (m, 2H), 3.96 - 3.90 (m, 1H), 3.86 - 3.81 (m, 1H), 3.72 (s, 6H), 3 41 - 3.36 (m, 1H), 3.35 (s, 3H), 3.29 - 3.24 (m, 1H), 2.92 (t, j= 5.8 Hz, 2H), 0.85 (s, 9H), 0.07 (s, 3H), 0.06 (s, 3H). 13C NMR (126 MHz, DMSO) d 163.12, 162.94, 158.11, 156.61, 150.25, 150.00, 144.34, 142.06, 140.09, 137.28, 135.07, 135.00, 129.75, 129.73, 127.77, 127.75, 126.72, 120.32, 117.92, (0829) 113.11, 101.99, 101.69, 91.76, 90.27, 90.06, 89.78, 87.33, 85.98, 81.43, 81.40, 81.37, 79.48, 79.41, 72.88, 72.74, 69.40, 66.71, 63.59, 63.55, 61.33, 57.62, 54.95, 25.54, 18.84, 18.77, 17.67, -4.86, -5.13. 31P NMR (202 MHz, DMSO) d 68.34. 19F NMR (376 MHz, DMSO) d - 203.36, -203.42, -203.47, -203.50, -203.56, -203.61. Molecular weight for (0830) C49H59FN5Oi4PSSi (M+Na): calculated 1074.368, found 1074.3198.

Reference： [1]Patent: WO2019/126651,2019,A1 .Location in patent: Page/Page column 113; 126-127

16
(2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl 4-oxopentanoate [ No CAS ]
[ 146954-75-8 ]
(2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((((2-cyanoethoxy)(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl)oxy)phosphorothioyl)oxy)methyl)-4-fluorotetrahydrofuran-3-yl 4-oxopentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
960 mg		(1) (i) (Coupling): (0408) 5'OH-3'-Levulinylated-2'F-deoxy-Adinosine ((3), 700 mg, 1.48 mmol) and 5'DMT-2'F- 3 'CED-Phosphoamidite-deoxy -Uridine ((4), 1.66 g, 2.22 mmol) mixture was dried under high vacuum for 1-2 hours. Argon was flushed over R.B. flask containing reaction mixture. Anhydrous acetonitrile (40 mL) was added to reaction mixture followed by ETT (279 mg, 2.146 mmol) in acetonitrile solution (5.0 mL) under an atmosphere of argon. The resulting mixture was stirred at room temperature under argon for 2 h. Once TLC analysis showed completion of the reaction, water was added (80 muEpsilon, 2 equivalents to amidite). The resulting mixture was carried onto the next step. (0409) (ii) (Sulfurization) : (0410) In a silanized flask, Beaucage reagent (3H-BD) (592 mg, 2.96 mmol) was dissolved in acetonitrile (5.0 mL). The above coupling reaction mixture containing (5) was added to the solution of sulfurizing reagent (3H-BD) in acetonitrile under an atmosphere of argon and the resulting mixture was stirred at room temperature for 45 minutes to allow the sulfurization reaction to go to completion. Methanol (10 mL) was then added and the resulting mixture was stirred for 30 min. The reaction mixture was concentrated under reduced pressure. The crude residue was dissolved in DCM (100 mL) and washed with water (75 mL). The organic layer was separated, dried over Na2SC"4, and used in the next step (detritylation). (0411) (2) Detritylation: The DCM solution containing the product from the previous step was cooled to ice-water bath in a R.B. flask. 5% PTSA solution in DCM:MeOH (7:3, 100 mL) was added and the resulting mixture stirred for 15 minutes to allow the detritylation reaction to go to completion. Water (50 mL) was then added and the resulting mixture was stirred for another 15 minutes. The reaction mixture was transferred to separatory funnel water and the phases were separated. The organic layer was washed 5% NaHCCb solution (100 mL) until the pH of the aqueous layer was adjusted to above 7.0. The organic layer was then dried over Na2S04 and concentrated under reduced pressure. The crude product was purified using Combiflash silica gel column chromatography eluting with 0-5% MeOH in DCM to give 960 mg of the desired product (5) as white solid.

Reference： [1]Patent: WO2018/9652,2018,A1 .Location in patent: Page/Page column 104; 105-107

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