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

Base Information

• Chemical Name: 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
• CAS No.: 478044-34-7
• Molecular Formula: C₄₆H₄₇BrN₆O₁₂P₂S₂
• Molecular Weight: 1081.9

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 7 articles about 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 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: 96.3%

dithiophenoxyphosphoryl chloride (273387-14-7) + 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) → 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 (478044-34-7)

Guidance literature:

With pyridine; 1H-tetrazole; triisopropylbenzenesulfonyl chloride; at 20 ℃; for 72h;

DOI:10.1021/jm010530l

Reference yield:

N,N'-diphenylphosphorodiamidic chloride (5625-99-0) → 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 (478044-34-7)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 96.3 percent / tetrazole; pyridine; triisopropylbenzenesulfonyl chloride / 72 h / 20 °C

With pyridine; 1H-tetrazole; triisopropylbenzenesulfonyl chloride; In dichloromethane;

DOI:10.1021/jm010530l

Reference yield:

5-O-benzoyl-3-O-allyl-1,4-anhydro-D-xylitol (478044-27-8) → 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 (478044-34-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium methoxide; MeOH / 20 °C

2.1: 6.05 g / pyridine / 48 h / 20 °C

3.1: pyridine / -15 °C

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

4.2: 34 percent / tetrahydrofuran / 24 h / 45 °C

5.1: 86 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

6.1: 95 percent / tetrazole; pyridine / 48 h / 20 °C

7.1: 79.6 percent / 5percent aq. Cl₃CCOOH / CH₂Cl₂ / 0.5 h

8.1: 96.3 percent / tetrazole; pyridine; triisopropylbenzenesulfonyl chloride / 72 h / 20 °C

With pyridine; 1H-tetrazole; methanol; 18-crown-6 ether; triisopropylbenzenesulfonyl chloride; tetrabutyl ammonium fluoride; sodium methylate; potassium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm010530l

upstream raw materials:

dithiophenoxyphosphoryl chloride

8-bromo-N¹-(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-benzoyl-3-O-allyl-1,4-anhydro-D-xylitol

Downstream raw materials:

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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