51348-66-4

Upstream product

• 547-65-9 α-methylene-γ-butyrolactone 
• 917506-89-9 methyl 4-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylenebutyrate 
• 101198-71-4 ethyl 4-acetoxy-3-hydroxy-2-methyl-2-(phenylthio)butyrate 
• 55859-92-2 (+/-)-Methyl β,γ-dihydroxy-α-methylenebutyrate 
• 73738-72-4 ethyl 4-acetoxy-3-hydroxy-2-methylenebutyrate 
• 101198-76-9 β-hydroxy-α-methyl-α-(phenylthio)-γ-butyrolactone 
• 128275-45-6 2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-propenal 
• 74006-38-5 2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-acrylic acid 
• 101198-77-0 3-Benzenesulfinyl-4-hydroxy-3-methyl-dihydro-furan-2-one 
• 123172-67-8 C₁₉H₁₆O₃ 
• 24923-78-2 α-Methylen-β,γ-dihydroxy-buttersaeure 
• 101198-75-8 3,4-Dihydroxy-2-methyl-2-phenylsulfanyl-butyric acid 

Relevant academic research and scientific papers

A NEW TEMPLATE of MITSUNOBU ACYLATE CLEAVABLE in NONALKALINE CONDITIONS

The Mitsunobu inversion is one of the reliable methods for stereospecific substitution of chiral alcohols, but its deacylation step has limited the substrate scope. Here, we propose a new template of the Mitsunobu acylate that can be deacylated in non-alkaline treatments. The 3,4-dihydroxy-2-methylenebutanoate was selected as a template structure, and its acetonide- or bisTBS derivatives were synthesized. The latter especially showed excellent inversion efficiency (up to >99% ee) and good elimination performance for a series of secondary alcohols in near-neutral conditions. The results demonstrated the applicability of the new template for the substrates labile in alkaline conditions, such as a-hydroxyesters.

Substrate specificity of tuliposide-converting enzyme, a unique non-ester-hydrolyzing carboxylesterase in tulip: Effects of the alcohol moiety of substrate on the enzyme activity

6-Tuliposides A (PosA) and B (PosB) are glucose esters accumulated in tulip (Tulipa gesneriana) as major defensive secondary metabolites. Pos-converting enzymes (TgTCEs), which we discovered previously from tulip, catalyze the conversion reactions of PosA

Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA

The enzyme MurA performs an essential step in peptidoglycan biosynthesis and is therefore a target for the discovery of novel antibacterial compounds. We report here the inhibition of MurA by natural products from tulips (tulipalines and tuliposides), and the structure-activity relationships of various derivatives. The inhibition of MurA can be related to antibacterial activity, and MurA is probably one of the relevant molecular targets of the tulipaline derivatives. MurA inhibition by this class of compounds depends on the presence of the substrate UNAG, which indicates non-covalent suicide inhibition as observed previously for cnicin. With respect to selectivity, however, the reactivity against arbitrary sulfhydryl groups, such as in glutathione, could not yet be sufficiently separated from MurA inhibition in the present dataset.

First total synthesis of 6-tuliposide B

Labile (+)-6-tuliposide B, an antimicrobial compound produced by tulip, was synthesized in nine steps from d-glucose via the Baylis-Hillman reaction of 2-(tert-butyldimethylsilyloxy)-acetaldehyde with 6-O-acryloyl-1-O-(2-trimethylsilylethyl)-β-d-glucopyranoside, followed by a mild deprotection procedure using TFA in CH2Cl2.

Synthesis of tulipalin B and 1-O-methyl-6-tuliposide B

Toward the total synthesis of 6-tuliposide B, facile synthesis of tulipalin B and 1-O-methyl-6-tuliposide B (Methyl 6-0-((S)-3′,4′-dihydroxy-2′-methylenebutanoyl)-β-D-glucopyranoside) has been achieved.

GLYCOLALDEHYDE MONOMER IN ORGANIC SYNTHESIS

The lithium alkoxide of glycolaldehyde can be generated and trapped in situ by keto- and ester enolates to yield the corresponding keto-epoxides and hydroxy lactones respectively.

Allergenic α-Methylene-γ-butyrolactones. Study of the Capacity of β-Acetoxy- and β-Hydroxy-α-methylene-γ-butyrolactones To Induce Allergic Contact Dermatitis in Guinea Pigs

(+/-)-Tulipalin B was prepared in six steps from phenyl sulfide and ethyl 2-bromopropionate.The sensitizing power in the skin of (+/-)-tulipalin A (1a) and B (1b) and of the β-acetoxy derivatives (1c) was studied.All are able to induce allergic contact de

Allergenic α-Methylene-γ-lactones. General Method for the Preparation of β-Acetoxy- and β-Hydroxy-α-methylene-γ-butyrolactones from Sulfoxides. Application to the Synthesis of a Tuliposide B Derivative

A general synthesis of β-hydroxy-α-methylene-γ-butyrolactones , which is based on the sulfoxide-sulfenate rearrangement, is presented.Several β-acetoxy-α-methylene-γ-butyrolactones have been prepared and transformed into the β-hydroxy-derivatives through base hydrolysis.This synthesis has been applied to the first preparation of (tetraacetoxybenzyl)tuliposide B (22).