136060-76-9

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

Preparation of intermediates for fluorinated lignans by conjugated and tandem additions on 3-fluorofuran-2(5H)-one

Two syntheses of 3-fluorofuran-2(5H)-one (1) based on Wittig-Horner reaction of ethyl (diethoxyphosphoryl)fluoroacetate (15) with 2-oxoethyl acetate (16) or on transformation of D-erythronolactone (10) are given. 3-Fluorofuran-2(5H)-one (1) and ethyl 2-fluorobut-2-enoate (2) undergo conjugate addition with soft nucleophiles based on arenecarboxaldehyde dithioacetals 7 to form 2-fluorolactones 3 and 2-fluoroalkanoates 4. Intermediate enolates can be trapped in the sense of tandem addition with arenecarboxaldehydes 8 or (arylmethyl)bromides 9 to form intermediates 5 and 6 for fluorolignans. Although the conjugate addition proceeds with low stereoselectivity yielding mixture of both diastereoisomers, the electrophile in tandem addition attacks the intermediary fluoroenolate exclusively anti to its bulky β-substituent in good accord with non-fluorinated furan-2(5H)-ones.

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.

An enantioselective synthesis of (2S,3R)-3-(N-Benzyloxycarbonyl)amino-1-chloro-4-phenylthiobutan-2-ol, a central intermediate of nelfinavir

(2S,3R)-3-(N-Benzyloxycarbonyl)amino-1-chloro-4-phenylthiobutan-2-ol 1 is a central intermediate of nelfinavir 2, which, being a potent HIV protease inhibitor, represents one of the most clinically efficacious anti AIDS drugs. Thus, a practical enantioselective synthesis of 1 has been devised which employs sodium erythorbate 9 as a chiral starting material. Consisting of the total 14-step functional group manipulations that proceed via methyl (2S,3R)-4-hydroxy-2,3-epoxybutyrate 8, the synthetic processes can dispense with chromatographic purification and provide architecturally complex 1 in 17% overall yield under a strict control of stereochemistry.

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.

Process and intermediates for chiral epoxides

Chiral epoxybutyrates are prepared in high yield from novel dihydro-3R-substituted sulfonyloxy-4R-hydroxy-2-(3H)furanones via based catalyzed alcoholysis. The product chiral epoxy butyrates are useful intermediates for the synthesis of 1-carba-1-dethia cephem antibiotics.

Enantioselective synthesis of loracarbef from sodium erythorbate

Sodium erythorbate (7) has been converted to loracarbef (1). Oxidation of sodium erythorbate to D erythronolactone (8) followed by selective monotosylation and treatment with sodium ethoxide provided ethyl (2S,3R) 4 hydroxy 2.3 epoxybutyrate (10). Swern oxidation of this epoxide into the aldehyde (11), imine formation with tert-butylglycinate and an enantioselective Staudinger reaction with phthalimidoacetyl chloride afforded the (3S,4S)-cis-β-lactam (13). Appropriate functional group manipulations followed by a Dieckmann condensation, chlorination, and protecting group removals gave the enantiomerically pure nucleus of loracarbef (24).