38965-80-9

Usage

InChI:InChI=1/C5H6O3/c1-3-4(6)2-8-5(3)7/h4,6H,1-2H2/t4-/m1/s1

Upstream product

• 123434-22-0 (S) methyl 4-acetoxy-3-hydroxy-2-methylenebutanoate 
• 883988-87-2 (S)-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-propenal 
• 73945-74-1 (+)-(S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol 
• 73945-75-2 Benzoic acid 2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-allyl ester 
• 189351-43-7 2(R),6(S)-2,6-di-(acetoxymethyl)-5-methylene-1,3-dioxan-4-one 
• 796989-44-1 2-bromo-1-butene-3,4-diol 
• 73945-76-3 (S)-2-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)propenic acid 
• 73945-71-8 (+)-Methyl β,γ-dihydroxy-α-methylenebutyrate 
• 73945-77-4 methyl (S)-2-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)propenoate 

Relevant academic research and scientific papers

A facile method for the preparation of α-methylene-γ-butyrolactones from tulip tissues by enzyme-mediated conversion

We developed a facile method of enzyme-mediated conversion of 6-tuliposide to α-methylene-γ-butyrolactone (tulipalin). We used a tuliposide-converting enzyme for the conversion of 6-tuliposides extracted from tulip tissues into the corresponding tulipalins in high yields within 2 h at pH 7.0. The resulting tulipalins were selectively extracted by using several organic solvents.

Purification and characterization of a tuliposide-converting enzyme from bulbs of tulipa gesneriana

An enzyme that catalyzes the stoichiometric conversion of 6-tuliposide into tulipalin was purified and characterized from bulbs of Tulipa gesneriana. The enzyme appeared to be a dimer, the relative molecular mass (Mr) of each subunit being 34,900; it had maximum activity and stability at neutral pH and moderate temperature. The enzyme preferentially acted on such glucose esters as 6-tuliposides, and to a lesser extent on /7-nitrophenylacetate.

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 (-)-tuliparin B utilizing 2-bromo-1-alkenes conveniently synthesized from the 3-0-substituted 1,2-dibromoalkane system by regioselective elimination

Synthesis of (-)-tulipalin B with a variety of biological properties including cutaneous allergenic activity, was accomplished by using the 2-bromo-1-alkenes synthesized by the regioselective HBr elimination reaction of 3-acyloxy-1,2-dibromoalkanes.

The asymmetric Baylis-Hillman reaction as a template in organic synthesis

The Bayils-Hillman reaction of camphor-based acrylates has been demonstrated to result in the formation of products with high optical purity. A model that explains these results and the use of these products in the formation of anti aldol adducts is discu

Use of Enzymatic Hydrolysis of Dimethyl Malates for a Short Synthesis of Tulipalin B and of Its Enantiomer

Pig liver esterase (PLE) hydrolyzes the ester function α to the hydroxyl group in dimethyl malate.This regiospecific reaction was used to synthesize (+)- and (-)-tulipalin B.