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

Base Information

• Chemical Name: 8-bromo-N¹-(5''-O-benzoyl-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-2',3'-di-O-acetylinosine
• CAS No.: 478044-37-0
• Molecular Formula: C₂₉H₃₁BrN₄O₁₁
• Molecular Weight: 691.489

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 4 articles about 8-bromo-N¹-(5''-O-benzoyl-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-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: 90.0%

8-bromo-N1-(5''-O-benzoyl-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-5'-O-(tert-butyldimethylsilyl)-2',3'-di-O-acetylinosine (478044-36-9) → 8-bromo-N1-(5''-O-benzoyl-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-2',3'-di-O-acetylinosine (478044-37-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 6h;

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-(5''-O-benzoyl-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-2',3'-di-O-acetylinosine (478044-37-0)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; triethylsilane; 18-crown-6 ether; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; 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-(5''-O-benzoyl-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-2',3'-di-O-acetylinosine (478044-37-0)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; 18-crown-6 ether; tetrabutyl ammonium fluoride; 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-(tert-butyldimethylsilyl)-2',3'-di-O-acetylinosine

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:

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

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

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