5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose

Base Information

• Chemical Name: 5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose
• CAS No.: 4613-71-2
• Molecular Formula: C16H18 O7
• Molecular Weight: 322.315
• Hs Code.: 2932190090
• Mol file: 4613-71-2.mol

Synonyms:1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-D-erythro-pentofuranose

Chemical Property of 5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose

Chemical Property:

• PSA: 88.13000
• LogP: 1.45320

Purity/Quality:

99% ^*data from raw suppliers

1,2-O-Di-O-acetyl-5-O-benzoyl-3-deoxy-D-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,2-Di-O-Acetyl-5-O-benzoyl-3-deoxy-D-erythro-pentofuranose is a used as a reactant in the synthesis of aminooxopyridopyrimidine nucleosides with antitumor cytotoxicity.

Technology Process of 5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose

There total 2 articles about 5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose 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: 80.0%

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate (4105-29-7) + acetic anhydride (108-24-7) → 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2)

Guidance literature:

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate; With acetic acid; for 2h; Heating;

acetic anhydride; With pyridine; dmap; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2008.03.079

Reference yield:

→ 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2)

Guidance literature:

DOI:10.1002/jps.2600541014

Reference yield: 93.0%

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → 2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine (143653-60-5)

Guidance literature:

With tin(IV) chloride; In acetonitrile;

DOI:10.1016/S0040-4039(00)74670-3

upstream raw materials:

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate

acetic anhydride

Downstream raw materials:

2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine

2'-O-Acetyl-5'-O-benzoyl-4-N-isobutyryl-3'-deoxycytidine

benzoic acid 4-acetoxy-5-(4-amino-5-oxo-5H-pyrido[2,3-d]pyrimidin-8-yl)-tetrahydro-furan-2-ylmethyl ester

3'-deoxycytidine

Refernces

• 1、 Rizzo,Dougherty,Breslow. "3'-Deoxy-2'-phosphoramidites of adenosine and 5-methyluridine used for the solid phase synthesis of unnatural 3'-deoxy-2'-5''-oligonucleotides". . p. 4129 - 4132. Retrieved 2007/10/02.