(2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl((2R,3S,4R,5R)-4-azido-5-(6-benzamido-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl)methyl 2-cyanoethyl phosphate

Base Information

• Chemical Name: (2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl((2R,3S,4R,5R)-4-azido-5-(6-benzamido-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl)methyl 2-cyanoethyl phosphate
• CAS No.: 1422956-11-3
• Molecular Formula: C₃₇H₄₇N₁₂O₁₁PSi
• Molecular Weight: 894.913
• Mol file: 1422956-11-3.mol

Synonyms:

Chemical Property of (2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl((2R,3S,4R,5R)-4-azido-5-(6-benzamido-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl)methyl 2-cyanoethyl phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl((2R,3S,4R,5R)-4-azido-5-(6-benzamido-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl)methyl 2-cyanoethyl phosphate

There total 2 articles about (2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl((2R,3S,4R,5R)-4-azido-5-(6-benzamido-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl)methyl 2-cyanoethyl phosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C58H65N12O13PSi → (2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl((2R,3S,4R,5R)-4-azido-5-(6-benzamido-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl)methyl 2-cyanoethyl phosphate (1422956-11-3)

Guidance literature:

With trichloroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1002/chem.201201999

Reference yield:

N-(9-((2R,3R,4S,5R)-3-azido-4-(tert-butyldimethylsilyloxy)-5(hydroxymethyl) tetrahydro-furan-2-yl)-9H-purin-6-yl)benzamide (1242450-41-4) + 5'-O-(4,4'-dimethoxytrityl)-N-acetyl-2'-deoxycytidine 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite (157543-67-4,157543-68-5,154110-40-4) → (2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl((2R,3S,4R,5R)-4-azido-5-(6-benzamido-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl)methyl 2-cyanoethyl phosphate (1422956-11-3)

Guidance literature:

N-(9-((2R,3R,4S,5R)-3-azido-4-(tert-butyldimethylsilyloxy)-5(hydroxymethyl) tetrahydro-furan-2-yl)-9H-purin-6-yl)benzamide; 5'-O-(4,4'-dimethoxytrityl)-N-acetyl-2'-deoxycytidine 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite; With 1H-tetrazole; In acetonitrile; at 20 ℃; for 1h; Inert atmosphere;

With pyridine; iodine; In tetrahydrofuran; water; acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;

With trichloroacetic acid; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c02982

Reference yield:

(2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl((2R,3S,4R,5R)-4-azido-5-(6-benzamido-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl)methyl 2-cyanoethyl phosphate (1422956-11-3) + bis(2-cyanoethyl) diisopropylamidophosphite (102690-88-0) → C43H54N14O14P2Si

Guidance literature:

(2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl((2R,3S,4R,5R)-4-azido-5-(6-benzamido-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl)methyl 2-cyanoethyl phosphate; bis(2-cyanoethyl) diisopropylamidophosphite; With 1H-tetrazole; In acetonitrile; at 20 ℃; for 3h; Inert atmosphere;

With pyridine; iodine; In tetrahydrofuran; water; acetonitrile; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c02982

upstream raw materials:

N-(9-((2R,3R,4S,5R)-3-azido-4-(tert-butyldimethylsilyloxy)-5(hydroxymethyl) tetrahydro-furan-2-yl)-9H-purin-6-yl)benzamide

5'-O-(4,4'-dimethoxytrityl)-N-acetyl-2'-deoxycytidine 3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite