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

Base Information

• Chemical Name: 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
• CAS No.: 478044-36-9
• Molecular Formula: C₃₅H₄₅BrN₄O₁₁Si
• Molecular Weight: 805.752

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 3 articles about 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 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: 26.8%

Benzoic acid (2R,3R,4S)-3-allyloxy-4-trifluoromethanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester + Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(8-bromo-6-oxo-1,6-dihydro-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester → 8-bromo-O6-(5''-O-benzoyl-1'',4''-anhydro-2''-deoxy-3''-O-allyl-D-ribitol-2''-yl)-5'-O-(tert-butyldimethylsilyl)-2',3'-di-O-acetylinosine + 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)

Guidance literature:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(8-bromo-6-oxo-1,6-dihydro-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester; With 18-crown-6 ether; potassium carbonate; In tetrahydrofuran; for 1h; Heating;

Benzoic acid (2R,3R,4S)-3-allyloxy-4-trifluoromethanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester; In tetrahydrofuran; at 45 ℃; for 24h; Further stages.;

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)-5'-O-(tert-butyldimethylsilyl)-2',3'-di-O-acetylinosine (478044-36-9)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; triethylsilane; 18-crown-6 ether; boron trifluoride diethyl etherate; 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)-5'-O-(tert-butyldimethylsilyl)-2',3'-di-O-acetylinosine (478044-36-9)

Guidance literature:

Multi-step reaction with 2 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

With pyridine; 18-crown-6 ether; potassium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm010530l

upstream raw materials:

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

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