[ CAS No. 136834-22-5 ] {[proInfo.proName]}

Name: 136834-22-5|(2R,3R,4R,5R)-5-(6-Benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite|95%
Brand: Ambeed
SKU: A122283
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2D 3D

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Quality Control of [ 136834-22-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 136834-22-5 ]

Product Details of [ 136834-22-5 ]

CAS No. :	136834-22-5	MDL No. :	MFCD12912392
Formula :	C₄₇H₅₁FN₇O₇P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VCCMVPDSLHFCBB-MSIRFHFKSA-N
M.W :	875.92	Pubchem ID :	12042896
Synonyms :		Chemical Name :	(2R,3R,4R,5R)-5-(6-Benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite

Safety of [ 136834-22-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 136834-22-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 136834-22-5 ]

[ 136834-22-5 ] Synthesis Path-Downstream 1~8

1
[ 136834-22-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
42.2%	Stage #1: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide With water; pyridinium trifluroacetate In acetonitrile at 20℃; for 0.0166667h; Stage #2: With <i>tert</i>-butylamine In acetonitrile for 0.166667h;	8 (2R,3R,4R,5RV5-(6-benzamido-9H-purin-9-yl)-2-((bis(4- methoxyphenyl^'Xphenvnmethoxy^'tmethvD^-fluorotetrahvdrofuran-S-yl hydrogen phosphonate To a solution of (2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4- methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite (2190 mg, 2.5 mmol) in acetonitrile (15 mL) and water (0.090 mL, 5.00 mmol) at room temperature was added pyridine 2,2,2-trifluoroacetate (579 mg, 3.00 mmol). The mixture was stirred for 1 minute, after which time LCMS indicated complete conversion to the first intermediate, m/z (M+H) = 793.3. Then, 2-methylpropan- 2-amine (13.14 mL, 125 mmol) was added and the mixture stirred for 10 minutes, after which time LCMS indicated consumption of the first formed intermediate.The mixture was concentrated in vacuo to afford a white foam. The foam was then dissolved in acetonitrile (20 mL) and concentrated. This process was repeated one more time. The crude material was dissolved in dichloromethane (10 mL) and purified by chromatography in two batches (silica gel, gradient elution of 0-30% methanol in dichloromethane). The desired fractions were combined and evaporated to afford two separate white solids which were then dissolved in dichloromethane, combined and evaporated to afford the titled compound (780 mg, 1 .055 mmol, 42.2 % yield) as a white solid. LCMS m/z 740.4 (M+H).
	Stage #1: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide With water; pyridinium trifluroacetate In acetonitrile for 0.166667h; Stage #2: With nitromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 0.333333h;	Preparation of Intermediate 1-1: A solution of (2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4- methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite (Sigma- Aldrich, 2 g, 2.3 mmol) in ACN (5 mL) was treated with water (0.05 mL, 2.7 mmol), followed by pyridine trifluoroacetate (0.53 g, 2.7 mmol) The colorless solution was stirred for 10 min. and then concentrated in vacuo to afford a light pink foam. The resulting solid was dissolved in MeCN (5 mL) and concentrate to dryness. The resulting material was again dissolved in MeCN (5 mL). A solution of DBU (2.75 mL, 18.3 mmol) in ACN (6 mL) and nitromethane (1 mL, 18.3 mmol.) was prepared. To this DBU solution was added the ACN solution from above in one portion and the mixture was stirred for 20 min. The reation was then poured into a 15 wt% aqueous solution of KH2PO4 (25 mL) and 2-MeTHF (20 mL) and agitated. The aqueous layer was extracted with 2-MeTHF (20 mL) and the combined organic layers were washed with a 15 wt% aqueous solution of KH2PO4 (2 x 20 mL), then a solution of brine (20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting gel was dried by azeotropic distillation with 2-MeTHF (30-40 mL/g total, charged in 8-10 mL amounts).
1 g	Stage #1: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide With water; pyridinium trifluroacetate In acetonitrile for 0.166667h; Stage #2: With nitromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 0.333333h; Further stages;	Preparation of Intermediate I-l: (2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-4- fluoro-2-(hydroxymethyl)tetrahydrofuran-3-yl hydrogen phosphonate A solution of (2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4- methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite (Sigma- Aldrich, 2 g, 2.3 mmol) in ACN (5 mL) was trea ed with water (0.05 mL, 2.7 mmol), followed by pyridine trifluoroacetate (0.53 g, 2.7 mmol) The colorless solution was stirred for 10 min. and then concentrated in vacuo to afford a light pink foam. The resulting solid was dissolved in MeCN (5 mL) and concentrate to dryness. The resulting material was again dissolved in MeCN (5 mL). A solution of DBU (2.75 mL, 18.3 mmol) in ACN (6 mL) and nitromethane (1 mL, 18.3 mmol.) was prepared. To this DBU solution was added the ACN solution from above in one portion and the mixture was stirred for 20 min. The reaction was then poured into a 15 wt% aqueous solution of KH2PO4 (25 mL) and 2-MeTHF (20 mL) and agitated. The aqueous layer was extracted with 2-MeTHF (20 mL) and the combined organic layers were washed with a 15 wt% aqueous solution of KH2PO4 (2 x 20 mL), then a solution of brine (20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting gel was dried by azeotropic distillation with 2-MeTHF (30-40 mL/g total, charged in 8-10 mL amounts). The crude material was then dissolved in DCM (20 mL). Methanol (1 mL) was added, followed by 2,2-dichloroacetic acid (0.8 mL, 10.8 mmol). The reaction was stirred for 3 h. To this mixture was added pyridine (2 mL, 27 mmol.) and then the mixture was concentrated in vacuo to a gel-like residue. Dimethoxy ethane (10 mL) was added and a white solid precipitated. The solids were collected by filtration and re-suspended in DME (2.5 mL/g) and agitated carefully with a spatula on the filter. The solids were again filtered and the process was repeated two more times to afford Intermediate 1-1 as a white powder. (1 g, 72%).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2017/93933, 2017, A1 Location in patent: Page/Page column 89-90
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2019/79261, 2019, A1 Location in patent: Page/Page column 76; 77
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2019/74887, 2019, A1 Location in patent: Page/Page column 87; 88

2
[ 136834-22-5 ]
[ 1834500-64-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide With pyridinium trifluroacetate In water; acetonitrile for 0.166667h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In nitromethane; acetonitrile for 0.333333h;	1-1; 1-2 Preparation of Intermediate IL: A solution of (2R,3R,4R,5R)-5-(6-benzamido-9Hpurin -9-yl )-2-( (bis( 4-methoxyphenyl )(pheny I )methoxy) methyl)-4-fluorotetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite (Sigma-Aldrich, 2 g, 2.3 mmol) in ACN (5 mL) was treated with water (0.05 mL, 2.7 mmol), followed by pyridine trifluoroacetate (0.53 g, 2.7 mmol) The colorless solution was stirred for 10 min. and then concentrated in vacuo to afford a light pink foam. The resulting solid was dissolved in MeCN (5 mL) and concentrated to dryness. The resulting material was again dissolved in MeCN (5 mL). A solution ofDBU (2.75 mL, 18.3 mmol) in ACN (6 mL) and nitromethane (I mL, 18.3 mmol) was prepared. To this DBU solution was added theACN solution from above in one portion and the mixture was stirred for 20 min. The reaction was then poured into a 15 wt % aqueous solution of KH2P04 (25 mL) and 2-MeTHF (20 mL) and agitated. The aqueous layer was extracted with 2-MeTHF (20 mL) and the combined organic layers were washed with a 15 wt % aqueous solution of KH2PO 4 (2x20 mL ), then a solution of brine (20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting gel was dried by azeotropic distillation with 2-MeTHF (30-40 mL/g total, charged in 8-10 mL amounts). The crude material was then dissolved in DCM (20 mL). Methanol (I mL) was added, followed by dichloroacetic acid (0.8 mL, 10.8 mmol). The reaction was stirred for 3 h. To this mixture was added pyridine (2 mL, 27 mmol) and then the mixture was concentrated in vacuo to a gel-like residue. Dimethoxyethane (10 mL) was added and a white solid precipitated. The solids were collected by filtration and re-suspended in DME (2.5 mL/g) and agitated carefully with a spatula on the filter. The solids were again filtered and the process was repeated two more times to afford Intermediate IL as a white powder (I g, 72%).
72%	Stage #1: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide With water; pyridinium trifluroacetate In acetonitrile for 0.166667h; Stage #2: With nitromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 0.333333h; Stage #3: With dichloro-acetic acid In methanol; dichloromethane for 3h;	Preparation of Intermediate 1-9: A solution of (2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4- methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite (Sigma- Aldrich, 2 g, 2.3 mmol) in ACN (5 mL) was treated with water (0.05 mL, 2.7 mmol), followed by pyridine trifluoroacetate (0.53 g, 2.7 mmol) The colorless solution was stirred for 10 min. and then concentrated in vacuo to afford a light pink foam. The resulting solid was dissolved in MeCN (5 mL) and concentrate to dryness. The resulting material was again dissolved in MeCN (5 mL). A solution of DBU (2.75 mL, 18.3 mmol) in ACN (6 mL) and nitromethane (1 mL, 18.3 mmol.) was prepared. To this DBU solution was added the ACN solution from above in one portion and the mixture was stirred for 20 min. The reation was then poured into a 15 wt% aqueous solution of KH2PO4 (25 mL) and 2-MeTHF (20 mL) and agitated. The aqueous layer was extracted with 2-MeTHF (20 mL) and the combined organic layers were washed with a 15 wt% aqueous solution of KH2PO4 (2 x 20 mL), then a solution of brine (20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting gel was dried by azeotropic distillation with 2-MeTHF (30-40 mL/g total, charged in 8-10 mL amounts). The crude material was then dissolved in DCM (20 mL). Methanol (1 mL.) was added, followed by dichloroacetic acid (0.8 mL, 10.8 mmol). The reaction was stirred for 3 h. To this mixture was added pyridine (2 mL, 27 mmol.) and then the mixture was concentrated in vacuo to a gel-like residue. Dimethoxy ethane (10 mL) was added and a white solid precipitated. The solids were collected by filtration and re-suspended in DME (2.5 mL/g) and agitated carefully with a spatula on the filter. The solids were again filtered and the process was repeated two more times to afford Intermediate 1-9 as a white powder. (1 g, 72%).
72%	Stage #1: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide With water; pyridinium trifluroacetate In acetonitrile for 0.166667h; Stage #2: With nitromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 0.333333h; Stage #3: With dichloro-acetic acid In methanol; dichloromethane for 3h;	Preparation of Intermediate 1-1: A solution of (2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4- methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite (Sigma- Aldrich, 2 g, 2.3 mmol) in ACN (5 mL) was treated with water (0.05 mL, 2.7 mmol), followed by pyridine trifluoroacetate (0.53 g, 2.7 mmol) The colorless solution was stirred for 10 min and then concentrated in vacuo to afford a light pink foam. The resulting solid was dissolved in MeCN (5 mL) and concentrated to dryness. The resulting material was again dissolved in MeCN (5 mL). A solution of DBU (2.75 mL, 18.3 mmol) in ACN (6 mL) and nitromethane (1 mL, 18.3 mmol) was prepared. To this DBU solution was added the ACN solution from above in one portion and the mixture was stirred for 20 min. The reaction was then poured into a 15 wt% aqueous solution of KH2PO4 (25 mL) and 2-MeTHF (20 mL) and agitated. The aqueous layer was extracted with 2-MeTHF (20 mL) and the combined organic layers were washed with a 15 wt% aqueous solution of KH2PO4 (2 x 20 mL), then a solution of brine (20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting gel was dried by azeotropic distillation with 2-MeTHF (30-40 mL/g total, charged in 8-10 mL amounts). The crude material was then dissolved in DCM (20 mL). Methanol (1 mL.) was added, followed by 2,2-dichloroacetic acid (0.8 mL, 10.8 mmol). The reaction was stirred for 3 h. To this mixture was added pyridine (2 mL, 27 mmol.) and then the mixture was concentrated in vacuo to a gel-like residue. Dimethoxy ethane (10 mL) was added and a white solid precipitated. The solids were collected by filtration and re-suspended in DME (2.5 mL/g) and agitated carefully with a spatula on the filter. The solids were again filtered and the process was repeated two more times to afford Intermediate 1-1 as a white powder (1 g, 72%).

	Multi-step reaction with 2 steps 1.1: water; pyridinium trifluroacetate / acetonitrile / 0.02 h / 20 °C 1.2: 0.17 h 2.1: dichloro-acetic acid; water / dichloromethane / 0.5 h / 20 °C
	Stage #1: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide With pyridinium trifluroacetate In water; acetonitrile at 20℃; for 0.0833333h; Stage #2: With <i>tert</i>-butylamine In water; acetonitrile at 20℃; for 0.25h; Further stages;	5′-OH-2′-F-3′-H-phosphonate-N⁶-Bz-2′-deoxyadenosine N6-Benzoyl-5′-DMT-2′-F-2′-deoxyadenosine-3′-CEP (obtained from Alfa Aesar) (1.05 g, 1.20 mmol) was dissolved in acetonitrile (6 mL) and water (0.043 mL, 2.40 mmol, 2 eq.) at room temperature. Pyridinium trifluoroacetate (278 mg, 1.44 mmol, 1.2 eq.) was added and the reaction mixture was stirred at room temperature for 5 minutes. Afterwards, tert-butylamine (6.0 mL, 57.1 mmol) was added and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was evaporated in vacuo, re-dissolved (2×) in anhydrous acetonitrile (12 mL) and again evaporated in vacuo to yield a white to colorless foam. The residue was dissolved in dichloromethane (14.4 mL) and water (0.22 mL, 12.0 mmol, 10 eq.). Dichloroacetic acid in dichloromethane (6%, 14.4 mL) was added and the resulting orange solution was stirred at room temperature for 10 minutes. Pyridine (1.64 mL, 20.3 mmol, 17 eq.) was added and the reaction mixture was evaporated in vacuo and azeotroped with anhydrous acetonitrile (3×11 mL). Finally the remaining crude product was dried in high vacuo for additional 30 min and used without further purification. LC-MS analytics of the raw material confirmed the presence of INTERMEDIATE 2.1. LC-MS (system E): tRet=0.64 min ESI-MS: 438 [M+H]+
	Stage #1: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide With pyridinium trifluroacetate; <i>tert</i>-butylamine In water; acetonitrile at 20℃; for 0.666667h; Stage #2: With dichloro-acetic acid In dichloromethane; water at 20℃; for 0.166667h;	5′-OH-2′-F-3′-H-phosphonate-N6-Bz-2′-deoxyadenosine 5′-DMTr-2′-F-3′-CEP-N6-Bz-2′-deoxyadenosine (obtained from ChemGenes, 0.654 g, 0.747 mmol) was dissolved in acetonitrile (10 mL) and water (0.033 mL, 1.50 mmol, 2 eq.) at room temperature. Pyridinium trifluoroacetate (0.173 g, 0.896 mmol, 1.2 eq.) was added and the reaction mixture was stirred at room temperature for 10 minutes. Afterwards, tent-butylamine (10 mL, 95.7 mmol) was added and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was evaporated under reduced pressure, re-dissolved in anhydrous acetonitrile (25 mL) and evaporated under reduced pressure. The residue was dissolved in dichloromethane (25 mL) and water (0.134 mL, 7.44 mmol, 10 eq.). Dichloroacetic acid (0.555 mL, 6.73 mmol, 9 eq.) in dichloromethane (25 mL) was added and the resulting orange solution was stirred at room temperature for 10 minutes. Pyridine (1.31 mL, 13.6 mmol, 18 eq.) was added and the reaction mixture was stirred at room temperature for 5 minutes. LC-MS analytics of the reaction mixture confirmed the presence of INTERMEDIATE 1.1. LC-MS (system A): tRet 4.22 min; ESI-MS: 438 [M+H]+ The solvents were evaporated under reduced pressure and the residue was azeotroped with anhydrous acetonitrile (4×15 mL). During the last evaporation procedure the solution was concentrated to ca. 4 mL of final azeotrope. The resulting anhydrous solution of INTERMEDIATE 1.1 was immediately used in the next sequence of reactions
	Multi-step reaction with 2 steps 1.1: pyridinium trifluroacetate; water / acetonitrile / 0.17 h 1.2: 0.33 h 2.1: dichloro-acetic acid / dichloromethane; methanol / 3 h
	Multi-step reaction with 2 steps 1.1: pyridinium trifluroacetate; water / acetonitrile / 0.17 h 1.2: 0.33 h 2.1: dichloro-acetic acid / methanol; dichloromethane / 3 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2019/30057, 2019, A1 Location in patent: Paragraph 1233; 1257; 1258
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2019/46498, 2019, A1 Location in patent: Page/Page column 96; 97
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2019/46496, 2019, A1 Location in patent: Page/Page column 70; 71
[4]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2017/93933, 2017, A1
[5]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US2018/92937, 2018, A1 Location in patent: Paragraph 0228; 0340-0344
[6]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US2018/273578, 2018, A1 Location in patent: Paragraph 0341-0346
[7]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2019/79261, 2019, A1
[8]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2019/74887, 2019, A1

3
[ 464-05-1 ]
(2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite [ No CAS ]
C₃₈H₃₅FN₅O₈P*C₅H₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.0%		[63] example 5 Step 1: preparation of compound 5b To a solution of DMT-2'-F-dA(Bz)-CE phosphoramidite 5a (2.20 g, 2.51 mmol) in CH3CN (12.0 mL) was added water (90.5 mg, 5.02 mmol, 2.0 eq) and <strong>[464-05-1]pyridinium trifluoroacetate</strong> (582.1 mg, 3.01 mmol, 1.2 eq). The mixture was stirred at 25 C for 5 min. Then tert-butylamine (12.0 mL) was added and the reaction mixture was stirred at 25 C for 15 min. The mixture was concentrated under reduced pressure to give a foam, which was dissolved in CH3CN (10.0 mL) and concentrated again to afford compound 5b (1.69 g, 2.29 mmol, 91.0% yield) as a white foam. ESI-MS: m/z 740.2 [M + H]+.

Reference： [1]Patent: WO2018/98203,2018,A1 .Location in patent: Page/Page column 63

4
[ CAS Unavailable ]
[ 136834-22-5 ]
[ 2242826-20-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 19h;	1.A Step A To a mixture of (2R, 3R,4R, 5R)-5 -(6-benzamido-9H-purin-9-yl)-2-((bi s(4- methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3 -yl (2-cyanoethyl) diisopropylphosphoramidite (Compound 100) (mixture of phosphorous diastereomers; 80.0 g, 91.332 mmol, 1 eq, ChemGenes Corporation catalog ANP-9151), allyl alcohol (9.63 ml, 142 mmol, 1.55 eq) and triphenylphosphine (38.3 g, 146 mmol, 1.60 eq)in THF (ilL) was added DEAD (40 wt% solution in toluene; 54.2 ml, 137 mmol, 1.5 eq.) at ambient temperature. Stirring was continued at ambient temperature and the reaction was monitored by LC/MS. Upon completion (19 h), the mixture was concentrated in vacuo (35 °C) and resultant mixture was purified by silica gel column chromatography (800 g x 2 columns, 40to 60% EtOAc in n-heptane buffered with 0.5% triethylamine) to give Compound 101 as awhite foam (84.2 g, quantitative yield, mixture of phosphorous diastereomers).‘H NMR (3:2 mixture of phosphorous diastereomers, 400 IVIFIz, CDC13) ö 1.14 - 1.21 (m, 12H) 2.40 (t, J=6.2 Hz, 1.2 H) 2.59 (t, J=6.2 Hz, 0.8 H) 3.27 (d, J=8.6 Hz, 1 H) 3.52 - 3.66 (m, 5H) 3.78 (s 2.4 H) 3.79 (s 3.6 H) 4.28 - 4.34 (m, 1 H) 4.84 - 4.96 (m, 0.4 H) 4.99 (d, J=5.5 Hz,2 H) 4.95 - 5.10 (m, 0.6 H) 5.05 (d, J=10.9 Hz, 1 H) 5.22 (br d, J=17.6 Hz, 1 H) 5.64 (br d,J=53.2 Hz, 0.6 H) 5.70 (br d, J=51.6 Hz, 0.4 H) 5.96 - 6.75 (m, 1 H) 6.20 (d, J16.0 Hz, 0.6H) 6.24 (d, J17.2Hz, 0.4 H) 6.74 - 6.79 (m, 4 H) 7.02 - 7.06 (m, 2H) 7.17 - 7.24 (m, 8 H)7.32 - 7.34 (m, 2 H) 7.41 - 7.44 (m, 2 H) 8.11 (s, 1H) 8.52 (s, 0.4 H) 8.54 (s, 0.6 H).
100%	With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 19h;

Reference： [1]Current Patent Assignee: EISAI CO LTD - WO2018/152450, 2018, A1 Location in patent: Page/Page column 55; 56
[2]Current Patent Assignee: EISAI CO LTD - WO2020/36199, 2020, A1 Location in patent: Paragraph 0045

5
[ CAS Unavailable ]
[ 136834-22-5 ]
[ 1427269-36-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: allyl alcohol; N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide In acetonitrile at 20℃; for 0.5h; Molecular sieve; Stage #2: With 1H-tetrazole In acetonitrile at 20℃; for 0.5h; Further stages;	Preparation of Intermediate 1-10: (2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl) (phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl (2-cyanoethyl) (0837) diisopropylphosphoramidite (5g, 5.71 mmol), was azeotropped with 5 mL of dry acetonitrile. Then 0.2 g of 4A molecular sieves and acetonitrile (15 mL) were added. To this mixture was added prop-2-en-l-ol (0.663 g, 11.42 mmol) and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added lH-tetrazole (0.800 g, 11.42 mmol) and the reaction was stirred at room temperature for an additional 30 min. To the reaction was then added 2-hydroperoxy-2-((2-hydroperoxybutan-2- yl)peroxy)butane (2.400 g, 11.42 mmol) and stirring was continued for 30 min. The reaction was then filtered through celite and the fitrate was concentrated. The residue was dissolved in DCM (15 mL) and 2,2-dichloroacetic acid (4.42 g, 34.2 mmol) was added drop wise. After stiring for 30 min, the reaction mixture was treated with saturated aqueous NaHCC , and then extracted with DCM (30 mL x 3). The combined organic layers were dried over Na2S04 and then concentrated in vacuo. The residue was purified on silica gel (0-10% MeOH/DCM) to give Intermediate I- 10 (2.86 g, 5.23 mmol, 92 % yield) m/z 547.2 (M+H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2019/46498, 2019, A1 Location in patent: Page/Page column 97

6
[ 2307168-96-1 ]
[ 136834-22-5 ]
[ 2307168-97-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: C₁₆H₁₇FN₆O₅ With 5-(ethylthio)-1H-tetrazole In acetonitrile at 20℃; for 0.5h; Molecular sieve; Inert atmosphere; Stage #2: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide In acetonitrile at 20℃; for 16h; Molecular sieve; Inert atmosphere; Stage #3: With (E)-N,N-dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide In acetonitrile for 0.166667h;	12 Preparation of Intermediate 12F: Intermediate 12E (0.47 g, 1.2 mmol) and 5-(ethylthio)-lH-tetrazole (0.32 g, 2.45 mmol) in a 50 mL flask with a stir bar was azeotroped with 4 mL of acetonitrile three times. Then, 100 mg of 4A molecular sieves and 4 mL of dry acetonitrile were added under a N2 atmosphere. This mixture (I) was stirred at room temperature for 30 min. (2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4- methoxyphenyl)(phenyl)methoxy)methyl)-4-fluorotetrahydrofuran-3-yl(2- cyanoethyl)diisopropylphosphoramidite (Sigma Aldrich, 1.50 g, 1.71 mmol) in a 20 mL vial was azeotroped with 2 mL of acetonitrile two times. Then, 100 mg of 4A molecular sieves and 2 mL of ACN were added. This mixture (II) was stirred at room temperature for 30 min. With positive N2 pressure, mixture II was added to mixture I. To achieve a complete transfer, the vial containing (II) was rinsed with 1 mL of ACN and added to the mixture (I). The reaction was then stirred at room temperature for 16h. Then, (E)-N,N- dimethyl-N'-(3-thioxo-3H-l,2,4-dithiazol-5-yl)forrnimidamide (0.28 g, 1.35 mmol) was added and the reaction was stirred for an additional 10 minutes. The yellow solution was then filtered and the filtrated was diluted with 30 mL of EtOAc, washed with aq.NaHCC, dried over Na2S04 and concentrated. The residue was purified on silica (24 g) eluting with 0-100% EtOAc/hexane (with 0.5% TEA) to give Intermediate 12F (1.02 g, 0.89 mmol, 74% yield) as a pair of diastereomers. MS (ES): m/z =1146.2[M+H]+

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2019/74887, 2019, A1 Location in patent: Page/Page column 154; 155

7
[ 1613726-32-1 ]
[ 136834-22-5 ]
[ 2005449-33-0 ]

Yield	Reaction Conditions	Operation in experiment
95.2%	Stage #1: (2R,3R,4R,5R)-5-(6-benzamido-9H-purin-9-yl)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)tetrahydrofuran-3-yl hydrogen phosphonate; N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide With pyridinium trifluroacetate In tetrahydrofuran; acetonitrile at 15℃; for 2h; Molecular sieve; Stage #2: With N,N-dimethyl-N'-(5-sulfanylidene-1,2,4-dithiazol-3-yl)methanimidamide In tetrahydrofuran; acetonitrile at 25℃; for 0.5h; Stage #3: With dichloro-acetic acid; water In dichloromethane at 20℃; for 1h;	5.5.4 Procedure for preparation of compound 4 A mixture of compound 2 (4 g, 7.3 mmol, 1 eq), compound 3 (7.0 g, 8.0 mmol, 1.1 eq), pyridine;2,2,2-trifluoroacetic acid (2.8 g, 14.6 mmol, 2 eq) and Molecular sieve 3 A (5 g) in 100 mL of dry CH3 CN and 25 mL of dry THF was stirred at 15°C for 2 hrs. LC-MS showed the reaction was complete and desired mass was detected. The resulted mixture was used directly and added N,N-dimethyl-N'-(5-thioxo-1,2,4-dithiazol-3-yl)formamidine (2.6 g, 12.8 mmol, 1.7 eq). The mixture was stirred at 25°C for 0.5 hr. LC-MS showed the reaction was complete and desired mass was detected. The mixture was filtered and the filtrate was concentrated under reduced pressure to give a residue. The obtained crude yellow oil (10 g, crude) was used directly and dissolved into 100 mL of DCM, H2O (1.3 g, 73.7 mmol, 1.3 mL, 10 eq) and 2,2-dichloroacetic acid (4.8 g, 36.9 mmol, 3.0 mL, 5 eq) were added. The mixture was stirred at 20°C for 0.5 hr. LC-MS showed the reaction was complete and desired mass was detected. The reaction mixture was quenched by addition of 10 mL of MeOH, and then 5 mL of Py was added. The mixture was concentrated under reduced pressure to give a residue, which was purified by flash silica gel chromatography (ISCO; 120 g SepaFlash Silica Flash Column, Eluent of 0-50% Methanol/Ethyl acetate gradient 100 mL/min) to afford Compound 4 (7.4 g, 7.0 mmol, 95.2% yield) as a yellow solid. MS (ESI) m/z: calcd. for [M+H]+, 1054.26; found, 1054.4 (M/1+H)+.

Reference： [1]Current Patent Assignee: BICYCLE THERAPEUTICS LIMITED - WO2020/165600, 2020, A1 Location in patent: Paragraph 00525

8
[ CAS Unavailable ]
[ 136834-22-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: C₄₃H₅₃N₅O₇Si; N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenyl-methoxy]methyl]-4-[2-cyanoethoxy-(diisopropylamino)phosphanyl]oxy-3-fluoro-tetrahydrofuran-2-yl]purin-6-yl]benzamide With 1H-tetrazole In acetonitrile at 20℃; for 1h; Molecular sieve; Inert atmosphere; Stage #2: With water; iodine In tetrahydrofuran; pyridine at 20℃;	9 [0252] Compound 1h (600 mg 0.8 mmol) and 2h (920 mg, 0.84 mmol) were dissolved in anhydrous CH3CN (18.0 mL), and 4Å molecular sieves powder (180 mg, 1 gr/100 mL) were added. The mixture was bubbled with Ar gas for 4 min. After stirring at rt for 10 min, 0.45 M tetrazole in CH3CN (4.1 mmol, 11 mL) was added at rt. After stirring for 1 h, the mixture was filtered and washed with anhydrous CH3CN. 0.02 M I2 (THF:Py:H2O, 8:1:1, v/v/v) was added until the color persisted. After stirring for 20-30 min at rt, the reaction was quenched with Na2SO3 (aq, until discoloration). The mixture was diluted with EtOAc, and the layers were separated. The organic phase was washed with sat. aq. NaHCO3 (1 x 50 mL) and sat. aq. NaCl (1 x 50 mL). The combined aqueous phase was back extracted with EtOAc (1 x 50 mL). The combined organic phases were evaporated to dryness, and the resulting crude was purified by reverse phase prep-HPLC (Column: C18 spherical 20-35 mm 100A 80 g, mobile phase: 0.05% NH4HCO3 in water, m/m)-ACN from 30% to 100%, flow rate: 35 mL/min) to afford 3h (1.1 g, 0.71 mmol, 88%) as a white foam. ESI-MS: m/z 1570.7 [M+H]+.

Reference： [1]Current Patent Assignee: ALIGOS THERAPEUTICS - WO2020/227421, 2020, A1 Location in patent: Paragraph 0252

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[ 136834-22-5 ] Synthesis Path-Downstream 1~8

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