153984-49-7

Upstream product

• 67814-68-0 2,3-O-isopropylidene-β-D-ribofuranose 
• 882-33-7 diphenyldisulfane 
• 107961-06-8 α-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose 
• 32257-17-3 5-Acetyl-2,3-O-isopropyliden-D-ribonolactone 
• 91510-81-5 α-1-(thiophenyl)-2,3-O-isopropylidene-5-O-(tert-butyldiphenylsilyl)-D-ribofuranose 

Downstream Products

• 107961-16-0 β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose 
• 157428-33-6 ((3aR,4R,6R,6aR)-2,2-Dimethyl-6-phenylsulfanyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-dimethyl-octyloxy-silane 
• 107961-06-8 α-1-deoxy-1-C-(phenylthio)-2,3-O-isopropylidene-5-O-acetyl-D-ribofuranose 

Relevant academic research and scientific papers

Long Range Intramolecular Glycosidation

Stereocontrolled synthesis of glycosides was achieved by intramolecular glycosidation of an aglycon tethered to the 4, 5 and 6 position of a thioglycoside donor.

Synthesis and Reductive Elimination Reactions of Aryl Thioglycosides

Treatment of the sugar hemiacetals 1, 5, 7, 10, 12 and 14 with ArSSAr (Ar = phenyl, 2-pyridyl, 2-benzothiazolyl) and trialkylphosphanes affords in an SN2 process the corresponding aryl thioglycosides 3, 6, 8, 9, 11, 13, 15 and 16 in good to exc

New Entry to the C-Glycosilation by means of Carbenoid Displacement Reaction. Its Application to the Synthesis of Showdomycin

The novel and stereoselective carbon-carbon bond-forming reaction at the anomeric center of carbohydrates has been developed by means of a carbenoid displacement reaction with phenyl thioglycosides.This reaction was suggested to proceed via the oxonium ion intermediates and has the following advantages: (i) the preferential participation of a carbenoid with a sulfur atom can restrict the reaction site; (ii) the reaction can be carried out under neutral reaction condition; and (iii) the introduction of various functionalities can be accomplished by manipulation of the organosulfur groups of the products.This synthetic strategy was successfully applied to the synthesis of antitumor agent, (+)-showdomycin, and would provide a general route to the other C-glycosides.