136060-76-9

Basic information

• Product Name: 2-O-Tosyl-D-erythro-1,4-lactone
• Synonyms: 2-O-Tosyl-D-erythro-1,4-lactone
• CAS NO: 136060-76-9
• Molecular Weight: 272.279
• Mol File: 136060-76-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-O-Tosyl-D-erythro-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-O-Tosyl-D-erythro-1,4-lactone(136060-76-9)
• EPA Substance Registry System: 2-O-Tosyl-D-erythro-1,4-lactone(136060-76-9)

Safety Data

• Hazardous Substances Data: 136060-76-9(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 15667-21-7 D-erythronolactone 

Downstream Products

• 136171-94-3 (2S,3R)-2,3-epoxy-4-hydroxybutanoic acid ethyl ester 
• 136060-82-7 Benzyl 4-hydroxy-2(S),3(R)-epoxybutyrate 
• 152785-40-5 2,3-Anhydro-D-erythronolactone 

Relevant articles and documents

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General Synthetic Approach to Rotenoids via Stereospecific, Group-Selective 1,2-Rearrangement and Dual S N Ar Cyclizations of Aryl Fluorides

A general synthetic approach to rotenoids is described, featuring 1) stereospecific, group-selective 1,2-rearrangements of epoxy alcohols, and 2) S N Ar oxy-cyclizations of aryl fluorides. The common intermediate epoxyketone, en route to (-)-rotenone and (-)-deguelin, was prepared from d -araboascorbic acid in five steps. Also described is the conversion of (-)-deguelin into oxidized congeners, (-)-tephrosin and (+)-12a- epi -tephrosin.

2-Fluoro-2-buten-4-olide, a New Fluorinated Synthon. Preparation; 1,2-, 1,4- And Tandem Additions

2-Fluoro-2-buten-4-olide (1) was prepared either by transformation of D-erythronolactone or by Wittig-Horner reaction of ethyl (diethoxyphosphoryl)fluoroacetate with acetoxyacetaldehyde followed by ring closure. It can be transformed by 1,2-addition of nitrogen or hard carbon nucleophiles to fluorinated hydroxyamides or diols and by 1,4-addition of soft carbon nucleophiles to β-alkylated 2-fluorobutan-4-olides. Tandem addition leads to α,β disubstituted 2-fluorobutan-4-olides which are intermediates for the synthesis of fluorinated lignans.