158466-54-7

Basic information

• Product Name: Ethyl (αZ,2R,4R)-2-(3,4-dimethoxyphenyl)-α-methyl-β-<(1,1-dimethylethoxy)carbonyl>-1,3-dioxane-4-prop-α-enoate
• CAS NO: 158466-54-7
• Molecular Weight: 436.502
• Mol File: 158466-54-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Ethyl (αZ,2R,4R)-2-(3,4-dimethoxyphenyl)-α-methyl-β-<(1,1-dimethylethoxy)carbonyl>-1,3-dioxane-4-prop-α-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl (αZ,2R,4R)-2-(3,4-dimethoxyphenyl)-α-methyl-β-<(1,1-dimethylethoxy)carbonyl>-1,3-dioxane-4-prop-α-enoate(158466-54-7)
• EPA Substance Registry System: Ethyl (αZ,2R,4R)-2-(3,4-dimethoxyphenyl)-α-methyl-β-<(1,1-dimethylethoxy)carbonyl>-1,3-dioxane-4-prop-α-enoate(158466-54-7)

Safety Data

• Hazardous Substances Data: 158466-54-7(Hazardous Substances Data)

Upstream product

• 158466-52-5 1,1-Dimethylethyl (αS,2R,4R)-α-hydroxy-2-(3,4-dimethoxyphenyl)-1,3-dioxane-4-acetate 
• 3699-66-9 ethyl 2-diethoxyphosphorylpropionate 
• 158466-53-6 1,1-Dimethylethyl (2R,4R)-2-(3,4-dimethoxyphenyl)-α-oxo-1,3-dioxane-4-acetate 

Downstream Products

• 158466-62-7 (2R,3R)-2-Methoxy-4-methyl-1-(phenylsulfoxy)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate 
• 158466-61-6 (2R,3R)-2-Methoxy-4-methyl-1-(phenylthio)-3-pentyl (4Z,3R)-5-(ethoxycarbonyl)-3-<oxy>-4-<(1,1-dimethylethoxy)carbonyl>-4-hexenoate 
• 109946-35-2 tautomycin 

Relevant articles and documents

Total Synthesis of Tautomycin

A convergent stereocontrolled synthesis of the antifungal antibiotic tautomycin, a potent protein phosphatases inhibitor, has been achieved first via key aldol coupling of two large subunits, a right-hand C1-C21 ketone and a left-hand aldehyde (left from C22).The C1-C10 segment was synthesized through a remote stereochemical control process using a spiroketal template.After joining with the C11-C18 segment, the spiroketal moiety was selectively constructed.Then the right-hand C1-C21 ketone was synthesized via Roush asymmetric crotylboration.The left-hand aldehyde was prepared from a C21-C26 segment and a dialkylmaleic anhydride segment.Completely stereoselective assemblage of the two subunits, the right-hand and the left-hand, was achieved by employing the Mukaiyama aldol reaction.Further functional group manipulation including desilylation, oxidation at C2, and deprotection of tert-butyl ester with concomitant anhydride formation provided tautomycin which was identical with the natural product.As a preliminary study, derivatizations and degradation of the natural product were also examined to support the total synthesis.