95475-52-8

Basic information

• Product Name: cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside
• Synonyms: cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside
• CAS NO: 95475-52-8
• Molecular Weight: 498.312
• Mol File: 95475-52-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside(95475-52-8)
• EPA Substance Registry System: cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranoside(95475-52-8)

Safety Data

• Hazardous Substances Data: 95475-52-8(Hazardous Substances Data)

Upstream product

• 108-93-0 cyclohexanol 
• 2873-29-2 D-glucal triacetate 
• 3240-34-4 [bis(acetoxy)iodo]benzene 

Relevant articles and documents

A Rapid and Diastereoselective Synthesis of 2-Deoxy-2-iodo-α-glycosides and its Mechanism for Diastereoselectivity

Reductive deiodination of 2-deoxy-2-iodo-glycoside is an efficient and practical approach for the synthesis of 2-deoxyglycosides, which are moieties of bioactive compounds. However, inseparable diastereoisomers are usually formed in the preparation of 2-deoxy-2-iodo-glycosides via glycosylation of glycals with alcohols using current methods. To overcome this problem, a rapid and diastereoselective transformation of glycals and alcohols into 2-deoxy-2-iodo-α-glycosides enabled by I 2 /PhI(OAc) 2 has been developed. 14 glycals, derived from 13 monosaccharides and one disaccharide, diastereoselectively yielded α-glycosides. Only in two cases the diastereoselectivity of the glycosylation was poor. The yields of glycosylation range from 73% to 95%, and the reactions are finished in only five minutes. Investigations for better diastereoselectivity by comparing I 2 /Ph(OAc) 2 - with I 2 /Cu(OAc) 2 -mediated glycosylations using UV analysis have been conducted.

An efficient method for the selective synthesis of 2-deoxy-2-iodo- glycosides by O-glycosidation of d-glucal using I2-Cu(OAc) 2

An efficient and convenient method for the synthesis of 2-deoxy-2-iodo-O-glycosides from tri-O-acetyl-d-glucal with various alcohols by using I2-Cu(OAc)2 is described. The 21 examples of corresponding glycosides were obtained in high