8-bromo-N¹-(5''-O-(monomethoxytrityl)-1'',4''-anhydro-3''-O-acetyl-2''-deoxy-L-lyxitol-2''-yl)-5'-O-dianilinophosphoryl-2',3'-di-O-acetylinosine

Base Information

• Chemical Name: 8-bromo-N¹-(5''-O-(monomethoxytrityl)-1'',4''-anhydro-3''-O-acetyl-2''-deoxy-L-lyxitol-2''-yl)-5'-O-dianilinophosphoryl-2',3'-di-O-acetylinosine
• CAS No.: 478044-23-4
• Molecular Formula: C₅₃H₅₂BrN₆O₁₃P
• Molecular Weight: 1091.91

Synonyms:

Chemical Property of 8-bromo-N¹-(5''-O-(monomethoxytrityl)-1'',4''-anhydro-3''-O-acetyl-2''-deoxy-L-lyxitol-2''-yl)-5'-O-dianilinophosphoryl-2',3'-di-O-acetylinosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 8-bromo-N¹-(5''-O-(monomethoxytrityl)-1'',4''-anhydro-3''-O-acetyl-2''-deoxy-L-lyxitol-2''-yl)-5'-O-dianilinophosphoryl-2',3'-di-O-acetylinosine

There total 6 articles about 8-bromo-N¹-(5''-O-(monomethoxytrityl)-1'',4''-anhydro-3''-O-acetyl-2''-deoxy-L-lyxitol-2''-yl)-5'-O-dianilinophosphoryl-2',3'-di-O-acetylinosine 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:

Trifluoro-methanesulfonic acid (4aS,7R,7aR)-2-phenyl-tetrahydro-furo[3,2-d][1,3]dioxin-7-yl ester → 8-bromo-N1-(5''-O-(monomethoxytrityl)-1'',4''-anhydro-3''-O-acetyl-2''-deoxy-L-lyxitol-2''-yl)-5'-O-dianilinophosphoryl-2',3'-di-O-acetylinosine (478044-23-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: K₂CO₃; 18-crown-6 / tetrahydrofuran / 1 h / Heating

1.2: 209 mg / tetrahydrofuran / 24 h / 45 °C

2.1: 90 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

3.1: 89 percent / tetrazole; pyridine / 48 h / 20 °C

4.1: 73.7 percent / 80percent aq. HOAc / 4 h / 70 °C

5.1: pyridine / 48 h / 20 °C

6.1: 406 mg / pyridine / 20 °C

With pyridine; 1H-tetrazole; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium carbonate; In tetrahydrofuran;

DOI:10.1021/jm010530l

Reference yield:

acetic anhydride (108-24-7) + C51H50BrN6O12P → 8-bromo-N1-(5''-O-(monomethoxytrityl)-1'',4''-anhydro-3''-O-acetyl-2''-deoxy-L-lyxitol-2''-yl)-5'-O-dianilinophosphoryl-2',3'-di-O-acetylinosine (478044-23-4)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1021/jm010530l

Reference yield:

N,N'-diphenylphosphorodiamidic chloride (5625-99-0) → 8-bromo-N1-(5''-O-(monomethoxytrityl)-1'',4''-anhydro-3''-O-acetyl-2''-deoxy-L-lyxitol-2''-yl)-5'-O-dianilinophosphoryl-2',3'-di-O-acetylinosine (478044-23-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / tetrazole; pyridine / 48 h / 20 °C

2: 73.7 percent / 80percent aq. HOAc / 4 h / 70 °C

3: pyridine / 48 h / 20 °C

4: 406 mg / pyridine / 20 °C

With pyridine; 1H-tetrazole;

DOI:10.1021/jm010530l

upstream raw materials:

acetic anhydride

N,N'-diphenylphosphorodiamidic chloride

8-bromo-N¹-(1'',4''-anhydro-2''-deoxy-3'',5''-O-benzylidene-L-lyxitol-2''-yl)-2',3'-di-O-acetylinosine

8-bromo-N¹-(1'',4''-anhydro-2''-deoxy-L-lyxitol-2''-yl)-5'-O-dianilinophosphoryl-2',3'-di-O-acetylinosine

Downstream raw materials:

8-bromo-N¹-(1'',4''-anhydro-5''-O-[bis-(phenylthio)phosphoryl]-3''-O-acetyl-2''-deoxy-L-lyxitol-2''-yl)-5'-O-dianilinophosphoryl-2',3'-di-O-acetylinosine

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