5335-81-9

Basic information

• Product Name: naphthalen-1-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside
• CAS NO: 5335-81-9
• Molecular Formula: C₂₄H₂₆O₉S
• Molecular Weight: 490.5228
• Mol File: 5335-81-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 586.6°C at 760 mmHg
• Flash Point: 289.5°C
• Density: 1.33g/cm³
• Vapor Pressure: 9.62E-14mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: naphthalen-1-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: naphthalen-1-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside(5335-81-9)
• EPA Substance Registry System: naphthalen-1-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside(5335-81-9)

Safety Data

• Hazardous Substances Data: 5335-81-9(Hazardous Substances Data)

Upstream product

• 529-36-2 1-Naphthalenethiol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 19879-84-6 tetraacetyl thioglucose 
• 90-14-2 1-Iodonaphthalene 
• 90-11-9 1-Bromonaphthalene 
• 780820-43-1 2-(trimethylsilyl)naphthalen-3-yl trifluoromethanesulfonate 

Relevant articles and documents

Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature

A mild, convenient and transition-metal-free protocol for the synthesis of aryl 1-thioglycosides is presentedviaarynes generatedin situcombined with glycosyl thiols in the presence of TBAF(tBuOH)4. The methodology provides a general and efficient way to prepare a series of functionalized thioglycosides in good to excellent yields with a perfect control of the anomeric configuration at room temperature. In addition, the reaction conditions tolerate a variety of the pentoses and hexoses, and the reaction also performs smoothly on protected monosaccharides and disaccharides.

Ni/Photoredox-Dual-Catalyzed Functionalization of 1-Thiosugars

A general protocol for functionalization of glycosyl thiols has been reported. This protocol is based on a single-electron Ni/photoredox dual-catalyzed cross coupling between 1-thiosugars and a broad range of aryl bromides and iodides as well as alkenyl and alkynyl halides. This base-free method gives access to a series of functionalized thioglycosides in moderate to excellent yields with a perfect control of the anomeric configuration. Moreover, it has been shown that this methodology may be transposed successfully to the continuous-flow photoredox chemistry.