57449-30-6

Usage

Uses

Used in Chemical Synthesis:
(2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate is used as a key intermediate in the synthesis of various complex organic molecules. Its unique structure allows for versatile chemical reactions, making it a valuable component in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate is used as a potential therapeutic agent. Its specific functional groups and stereochemistry may contribute to its biological activity, offering opportunities for the development of new drugs with novel mechanisms of action.
Used in Material Science:
(2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate may also find applications in material science, where its structural features could be leveraged to create new materials with unique properties. These materials could have uses in coatings, adhesives, or as components in advanced composites.
Further research is essential to determine the full scope of applications for (2E)-but-2-en-1-yl (3S,4S,5S)-3,4,5-trihydroxy-6-oxocyclohex-1-ene-1-carboxylate, as its complex structure and potential reactivity may unlock new possibilities across various industries.

Upstream product

• 107-93-7 (E)-but-2-enoic acid 
• 40980-53-8 (-)-gabosine C 
• 101247-85-2 6-(tert-butyl)dimethylsiloxy-2-crotonyloxymethyl-4,5-isopropylidenedioxy-cyclohex-2-enone 
• 130021-73-7 methyl 3,4-O-cyclohexylidenequinate 
• 63167-70-4 Methyl 6-O-benzoyl-2,3-O-isopropylidene-α-D-mannopyranoside 
• 63167-71-5 methyl 6-O-benzoyl-2,3-O-isopropylidene-α-D-talopyranoside 
• 110694-76-3 (E)-But-2-enoic acid (1S,2S,6R,7S,8S,9S)-7-methoxy-4,4-dimethyl-9-(3-trifluoromethyl-pyridine-2-sulfinyl)-3,5,10-trioxa-tricyclo[5.2.1.0^2,6]dec-8-ylmethyl ester 
• 128044-87-1 (1R,2R,3S)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-methoxycarbonyl-4-cyclohexen-1,2,3-triol 
• 128044-89-3 (1R,2S,3S,4R,5R)-2-O-Acetyl-3-O-tert-butyldimethylsilyl-4,5-O-cyclohexylidene-1-methoxycarbonyl-cyclohexan-1,2,3,4,5-pentaol 
• 128044-90-6 (1R,2R,3S,4R)-4-O-Acetyl-3-O-tert-butyldimethylsilyl-1,2-O-cyclohexylidene-5-methoxycarbonyl-5-cyclohexen-1,2,3,4-tetraol 
• 128044-92-8 (1R,2R,3S,4R)-3-O-tert-Butyldimethylsilyl-5-crotonyloxymethyl-1,2-O-cyclohexylidene-5-cyclohexen-1,2,3,4-tetraol 
• 128044-88-2 (1R,2R,3S,4R,5R)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-methoxycarbonyl-cyclohexane-1,2,3,4,5-pentaol 
• 128044-91-7 (1R,2R,3S,4R)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-hydroxymethyl-5-cyclohexen-1,2,3,4-tetraol 
• 193888-32-3 3,4-O-cyclohexylidene-5-oxoquinate 

Downstream Products

• 40980-53-8 (-)-gabosine C 
• 57449-33-9 (4R,5R,6R)-2-(4-Bromo-phenylsulfanylmethyl)-4,5,6-trihydroxy-cyclohex-2-enone 
• 57449-32-8 (4R,5R,6R)-4,5,6-Trihydroxy-2-(2-hydroxy-ethylsulfanylmethyl)-cyclohex-2-enone 
• 57449-31-7 (E)-But-2-enoic acid 2,3,5-triacetoxy-benzyl ester 

Relevant academic research and scientific papers

Enantiospecific Synthesis of 2-Crotonyloxy-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) from Quinic Acid

A thirteen-step synthesis of the glyoxalase I inhibitor COTC (2-crotonyloxy-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone) from quinic acid is described.

Application of a tandem seleno-michael/aldol reaction in the total syntheses of (+)-Pericosine B, (+)-Pericosine C, (+)-COTC and 7-chloro-analogue of (+)-Gabosine C

Synthesis of (+)-Pericosine B, (+)-Pericosine C, (+)-COTC and a 7-chloro-analogue of (+)-Gabosine C was achieved via tandem seleno-Michael/aldol reactions as key steps. The carbasugar linear precursor was obtained from cheap and readily available D-ribose in 7 steps which included resolution of the D-ribopyranose and the D-ribofuranose forms. Further transformation of the cyclic product involving a regioselective Steglich esterification or methylation of the secondary hydroxyl group gave rise to protected (+)-COTC, (+)-Pericosine B and (+)-Pericosine C. Deprotection of benzyl ethers at ?78 °C gave the titled compounds in satisfactory yields.

Arene cis-dihydrodiols: Useful precursors for the preparation of analogues of the anti-tumour agent, 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC)

The synthesis of 6-epi-COTC, a diastereoisomer of Streptomyces metabolite 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC), is described. The anti-cancer activities of the novel analogue, in racemic and enantiomerically pure forms, a

High-pressure mediated asymmetric Diels-Alder reaction of chiral sulfinylacrylate derivatives and its application to chiral synthesis of (-)-COTC and (-)-gabosine C

The asymmetric Diels-Alder reactions of chiral sulfinylacrylate derivatives (1 and 2) with dienes (3-12) were examined under high-pressure (1.2 GPa) conditions. The endo cycloadduct (13e) obtained from sulfinyl acrylate (1) and 2-methoxyfuran (5) was converted to (-)-COTC (25) and (-)-gabosine C (26).

A new synthesis of the Glyoxalase-I inhibitor COTC

A stereoselective, chiral synthesis of the glyoxalase I inhibitor 2- crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone 1 (COTC) from a simple derivative of (-)-quinic acid is described. (C) 2000 Elsevier Science Ltd.

Total synthesis of a glyoxalase I inhibitor and its precursor, (-)-KD16-U1

A glyoxalase I inhibitor and (-)-KD16-U1 have been synthesized from D-ribonic acid γ-lactone through SnCl4-promoted cyclization of a phenylsulfonyl enol silyl ether and regioselective introduction of a hydroxymethyl group.

High pressure mediated asymmetric diels-alder reaction of chiral sulfinylacrylate derivatives with furan and 2-methoxyfuran

Asymmetric Diels-Alder reaction of chiral sulfinylacrylate derivatives (1 and 2) with furan (3) and 2-methoxyfuran (4) proceeded under high pressure (1.2 GPa) conditions to give endo cycloadducts (6c-f). The absolute configuration of adduct (6) was confir

ENANTIOSELECTIVE TOTAL SYNTHESIS OF GLYOXALASE I INHIBITOR USING ASYMMETRIC DIELS-ALDER REACTION OF A NEW CHIRAL DIENOPHILE, (S)S-3-(3-TRIFLUOROMETHYLPYRID-2-YLSULFINYL)ACRYLATE.

Highly enantioselective total synthesis of Glyoxalase I inhibitor (1) was achieved utilizing the assymetric Diels-Alder reaction of a new chiral dienophile, (S)S-menthyl 3-(3-trifluoromethylpyrid-2-ylsulfinyl)acrylate (3) with 2-methoxyfuran.