3-propenyl (2',3'-O,N⁴-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate

Base Information

• Chemical Name: 3-propenyl (2',3'-O,N⁴-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate
• CAS No.: 302346-93-6
• Molecular Formula: C₅₃H₅₇N₄O₂₂PS
• Molecular Weight: 1165.09

Synonyms:3-propenyl (2',3'-O,N⁴-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate

Chemical Property of 3-propenyl (2',3'-O,N⁴-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 3-propenyl (2',3'-O,N⁴-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate

There total 10 articles about 3-propenyl (2',3'-O,N⁴-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate 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: 80.0%

methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate (302346-92-5) + 3-propenyl-(2',3'-O,N4-tribenzoyl cytidine-5')-yl-N,N'-diisopropylphosphoramidite (302346-91-4) → 3-propenyl (2',3'-O,N4-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate (302346-93-6)

Guidance literature:

methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate; 3-propenyl-(2',3'-O,N⁴-tribenzoyl cytidine-5')-yl-N,N'-diisopropylphosphoramidite; With 1H-tetrazole; In acetonitrile; at -40 ℃; for 2h;

With 3,3-dimethyldioxirane; In acetone; at -40 ℃; for 1h; Further stages.;

DOI:10.1021/jo000646+

Reference yield:

4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester (84380-10-9) → 3-propenyl (2',3'-O,N4-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate (302346-93-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: HF / pyridine / 4 h / 0 - 20 °C

2.1: 65 percent / BF₃*Et₂O / CH₂Cl₂ / 12 h / 20 °C

3.1: 80 percent / NaOMe / methanol / 0.5 h / -40 °C

4.1: tetrazole / acetonitrile / 2 h / -40 °C

4.2: 80 percent / dimethyldioxirane / acetone / 1 h / -40 °C

With 1H-tetrazole; boron trifluoride diethyl etherate; hydrogen fluoride; sodium methylate; In pyridine; methanol; dichloromethane; acetonitrile; 1.1: Substitution / 2.1: Substitution / 3.1: Deacetylation / 4.1: Substitution / 4.2: Oxidation;

DOI:10.1021/jo000646+

Reference yield:

5-acetamido-4,7,8,9-tetra-O-acetyl-2,3,5-trideoxy-2-fluoro-D-glycero-α-D-galacto-2-nonulosonic acid methyl ester (91041-78-0) → 3-propenyl (2',3'-O,N4-tribenzoyl cytidine-5')-yl (methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid-2))-yl phosphorothioate (302346-93-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 65 percent / BF₃*Et₂O / CH₂Cl₂ / 12 h / 20 °C

2.1: 80 percent / NaOMe / methanol / 0.5 h / -40 °C

3.1: tetrazole / acetonitrile / 2 h / -40 °C

3.2: 80 percent / dimethyldioxirane / acetone / 1 h / -40 °C

With 1H-tetrazole; boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane; acetonitrile; 1.1: Substitution / 2.1: Deacetylation / 3.1: Substitution / 3.2: Oxidation;

DOI:10.1021/jo000646+

upstream raw materials:

methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate

3-propenyl-(2',3'-O,N⁴-tribenzoyl cytidine-5')-yl-N,N'-diisopropylphosphoramidite

4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester

5-acetamido-4,7,8,9-tetra-O-acetyl-2,3,5-trideoxy-2-fluoro-D-glycero-α-D-galacto-2-nonulosonic acid methyl ester

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