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

Base Information

• Chemical Name: 8-bromo-N¹-(1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl)-5'-O-(dianilinophosphoryl)-2',3'-di-O-acetylinosine
• CAS No.: 478044-33-6
• Molecular Formula: C₃₄H₃₈BrN₆O₁₁P
• Molecular Weight: 817.587

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

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

Chemical Property:

Purity/Quality:

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

There total 7 articles about 8-bromo-N¹-(1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-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: 79.6%

8-bromo-N1-(5''-O-(monomethoxytrityl)-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl)-5'-O-(dianilinophosphoryl)-2',3'-di-O-acetylinosine (478044-32-5) → 8-bromo-N1-(1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl)-5'-O-(dianilinophosphoryl)-2',3'-di-O-acetylinosine (478044-33-6)

Guidance literature:

With 5percent aq. Cl₃CCOOH; In dichloromethane; for 0.5h;

DOI:10.1021/jm010530l

Reference yield:

N,N'-diphenylphosphorodiamidic chloride (5625-99-0) → 8-bromo-N1-(1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl)-5'-O-(dianilinophosphoryl)-2',3'-di-O-acetylinosine (478044-33-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / tetrazole; pyridine / 48 h / 20 °C

2: 79.6 percent / 5percent aq. Cl₃CCOOH / CH₂Cl₂ / 0.5 h

With pyridine; 1H-tetrazole; In dichloromethane;

DOI:10.1021/jm010530l

Reference yield:

(3S,4R,5R)-4-Allyloxy-5-hydroxymethyl-tetrahydro-furan-3-ol → 8-bromo-N1-(1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl)-5'-O-(dianilinophosphoryl)-2',3'-di-O-acetylinosine (478044-33-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 6.05 g / pyridine / 48 h / 20 °C

2.1: pyridine / -15 °C

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

3.2: 34 percent / tetrahydrofuran / 24 h / 45 °C

4.1: 86 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

5.1: 95 percent / tetrazole; pyridine / 48 h / 20 °C

6.1: 79.6 percent / 5percent aq. Cl₃CCOOH / CH₂Cl₂ / 0.5 h

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

DOI:10.1021/jm010530l

upstream raw materials:

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

N,N'-diphenylphosphorodiamidic chloride

5-O-(monomethoxytrityl)-3-O-allyl-1,4-anhydro-D-xylitol

Trifluoro-methanesulfonic acid (3S,4S,5R)-4-allyloxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester

Downstream raw materials:

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

N¹-[5''-O-(phenylthio)phosphoryl-2''-deoxy-3''-O-allyl-D-lyxitol-2''-yl]-5'-O-phosphoryl-2',3'-di-O-acetylinosine

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