1015447-26-3

Basic information

• Product Name: 2,3,5-Tri-O-benzoyl-1-O-acetyl-4-thio-D-ribofuranose
• Synonyms: 2,3,5-Tri-O-benzoyl-1-O-acetyl-4-thio-D-ribofuranose;b-D-Ribofuranose, 4-thio-, 1-acetate 2,3,5-tribenzoate;4-Thio-beta-D-ribofuranose 1-acetate 2,3,5-tribenzoate;1-O-Acetyl-2,3,5-tri-O-benzoyl-4-thio-b-D-ribofuranose
• CAS NO: 1015447-26-3
• Molecular Formula: C₂₈H₂₄O₈S
• Molecular Weight: 520.55036
• Mol File: 1015447-26-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,5-Tri-O-benzoyl-1-O-acetyl-4-thio-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-Tri-O-benzoyl-1-O-acetyl-4-thio-D-ribofuranose(1015447-26-3)
• EPA Substance Registry System: 2,3,5-Tri-O-benzoyl-1-O-acetyl-4-thio-D-ribofuranose(1015447-26-3)

Safety Data

• Hazardous Substances Data: 1015447-26-3(Hazardous Substances Data)

Usage

General Description

2,3,5-Tri-O-benzoyl-1-O-acetyl-4-thio-D-ribofuranose is a chemical compound with a complex molecular structure. It is a derivative of D-ribose, a type of sugar, and has three benzoyl groups and an acetyl group attached to the ribofuranose ring. Additionally, it contains a thio group attached to the fourth carbon of the ribofuranose ring. 2,3,5-Tri-O-benzoyl-1-O-acetyl-4-thio-D-ribofuranose is commonly used in organic synthesis and medicinal chemistry as a building block for the synthesis of various biologically active molecules. Its unique structure and reactivity make it a valuable tool for the development of new drugs and research in the field of carbohydrate chemistry.

Upstream product

• 115459-50-2 2,3,5-Tri-O-benzoyl-D-ribofuranose 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 108-24-7 acetic anhydride 
• 1015447-25-2 methyl 2,3,5-tri-O-benzoyl-α,β-4-thio-D-ribofuranoside 

Relevant articles and documents

Chemical synthesis of 4′-thio and 4′-sulfinyl pyrimidine nucleoside analogues

Analogues of the canonical nucleosides required for nucleic acid synthesis have a longstanding presence and proven capability within antiviral and anticancer research. 4′-Thionucleosides, that incorporate bioisosteric replacement of furanose oxygen with sulfur, represent an important chemotype within this field. Established herein is synthetic capability towards a common 4-thioribose building block that enables access to thio-ribo and thio-arabino pyrimidine nucleosides, alongside their 4′-sulfinyl derivatives. In addition, this building block methodology is templated to deliver 4′-thio and 4′-sulfinyl analogues of the established anticancer drug gemcitabine. Cytotoxic capability of these new analogues is evaluated against human pancreatic cancer and human primary glioblastoma cell lines, with observed activities ranging from low μM to >200 μM; explanation for this reduced activity, compared to established nucleoside analogues, is yet unclear. Access to these chemotypes, with thiohemiaminal linkages, will enable a wider exploration of purine and triphosphate analogues and the application of such materials for potential resistance towards relevant hydrolytic enzymes within nucleic acid biochemistries.

A facile and practical synthesis of peracylated 4-thio-D-ribofuranoses from D-glucose

(Chemical Equation Presented) A practical synthesis of a peracylated 4-thio-D-ribofuranose 14 starting from inexpensive D-glucose is described. The C2-C6 portion of D-glucose was utilized, in which sulfur was introduced to C5 in two consecutive displacement reactions with net retention of configuration under mild conditions.