2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl azide

Base Information

• Chemical Name: 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl azide
• CAS No.: 7408-41-5
• Molecular Formula: C26H21N3O7
• Molecular Weight: 487.469
• Mol file: 7408-41-5.mol

Synonyms:(2R,3R,4R,5R)-2-azido-5-(benzoyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate; 2,3,5-Tri-O-benzoyl-b-D-ribofuranosylazide; benzoic acid (2R,3R,4R,5R)-3,4-dibenzoyloxy-5-azido-tetrahydro-furan-2-ylmethyl ester; 2,3,4,6-TETRA-O-ACETYL-1-S-ACETYL-1-THIO-A-D-GALACTOPYRANOSIDE;

Chemical Property of 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl azide

Chemical Property:

• PSA: 137.88000
• LogP: 3.78256
• Solubility.: Chloroform, DCM. DMSO

Purity/Quality:

99% ^*data from raw suppliers

2,3,5-Tri-O-benzoyl-β-D-ribofuranosylAzide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl Azide is an intermediate in the synthesis of novel ribonucleosides with potential antiviral activities.

Technology Process of 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl azide

There total 7 articles about 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl azide 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: 100.0%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl azide (7408-41-5)

Guidance literature:

With trimethylsilylazide; tin(IV) chloride; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1016/0008-6215(92)80068-C

Reference yield: 98.0%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + trimethylsilylazide (4648-54-8) → 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl azide (7408-41-5)

Guidance literature:

With aluminium trichloride; In dichloromethane; at 0 ℃; for 0.166667h;

DOI:10.1016/0008-6215(83)84025-7

Reference yield: 11.0%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) → 2,3,5-tri-O-benzoyl-α-D-ribofuranosyl azide (70832-65-4) + 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl azide (7408-41-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; In dichloromethane; for 216h; Ambient temperature; other catalysts;

DOI:10.1016/0008-6215(92)80068-C

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

trimethylsilylazide

methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Downstream raw materials:

C₃₆H₃₂N₂O₁₀

4,5-bis-(chloromethyl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,3-triazole

5-Methyl-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,3-triazol

(1R,6R,7R,8S)-3-Phenyl-4,9-dioxa-2-azabicyclo<4.2.1>non-2-en-7,8-diyl-dibenzoat

Refernces

• 1、 Srivastava, Smriti,Bimal, Devla,Bohra, Kapil,Singh, Balram,Ponnan, Prija,Jain, Ruchi,Varma-Basil, Mandira,Maity, Jyotirmoy,Thirumal,Prasad, Ashok K.. "Synthesis and antimycobacterial activity of 1-(β-D-Ribofuranosyl)-4-coumarinyloxymethyl- / -coumarinyl-1,2,3-triazole". . p. 268 - 281. Retrieved 2018/03/21.
• 2、 Du,Yu,Deng,Lu,Li. "Synthesis, Antiplatelet Aggregation Activity Evaluation and 3D-QSAR of a Series of Novel 6-Alkylamino(Alkoxyl)-2-Propylthio-8-Azapurine Nucleosides". . p. 436 - 449. Retrieved 2017/02/05.