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

Base Information

• Chemical Name: 8-bromo-N¹-(1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-5'-O-(dianilinophosphoryl)-inosine
• CAS No.: 478044-39-2
• Molecular Formula: C₃₀H₃₄BrN₆O₉P
• Molecular Weight: 733.513

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 6 articles about 8-bromo-N¹-(1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-5'-O-(dianilinophosphoryl)-inosine 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: 95.0%

8-bromo-N1-(5''-O-benzoyl-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-5'-O-(dianilinophosphoryl)-2',3'-di-O-acetylinosine (478044-38-1) → 8-bromo-N1-(1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-5'-O-(dianilinophosphoryl)-inosine (478044-39-2)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1021/jm010530l

Reference yield:

3-O-Allyl-5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose (158895-32-0) → 8-bromo-N1-(1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-5'-O-(dianilinophosphoryl)-inosine (478044-39-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 83 percent / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 20 °C

2.1: pyridine / CH₂Cl₂ / 1 h

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

3.2: 26.8 percent / tetrahydrofuran / 24 h / 45 °C

4.1: 90 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

5.1: 93 percent / tetrazole; pyridine / 48 h / 20 °C

6.1: 95 percent / CH₃ONa; MeOH

With pyridine; 1H-tetrazole; methanol; triethylsilane; 18-crown-6 ether; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; potassium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm010530l

Reference yield:

5-O-benzoyl-3-O-allyl-1,4-anhydro-D-ribitol (478044-35-8) → 8-bromo-N1-(1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-5'-O-(dianilinophosphoryl)-inosine (478044-39-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / CH₂Cl₂ / 1 h

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

2.2: 26.8 percent / tetrahydrofuran / 24 h / 45 °C

3.1: 90 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

4.1: 93 percent / tetrazole; pyridine / 48 h / 20 °C

5.1: 95 percent / CH₃ONa; MeOH

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

DOI:10.1021/jm010530l

upstream raw materials:

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

N,N'-diphenylphosphorodiamidic chloride

3-O-Allyl-5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose

5-O-benzoyl-3-O-allyl-1,4-anhydro-D-ribitol

Downstream raw materials:

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

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

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

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

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