62532-49-4

Usage

InChI:InChI=1/C11H14O6/c1-2-3-8(13)17-5-6-4-7(12)10(15)11(16)9(6)14/h2-4,7,10-12,15-16H,5H2,1H3/b3-2+/t7-,10-,11+/m1/s1

Upstream product

• 107-93-7 (E)-but-2-enoic acid 
• 40980-53-8 (-)-gabosine C 
• 131221-92-6 (4R,5R,6R)-6-O-tert-Butyldimethylsilyl-2-crotonyloxymethyl-4,5-O-cyclohexylidene-4,5,6-trihydroxycyclohex-2-enone 
• 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 
• 175228-10-1 (1S)-2-endo-crotonyloxymethyl-5,6-O,O-isopropylidene-5,6-exo-dihydroxy-3-endo-({(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}methylsulfonyl)-1-methoxy-7-oxabicyclo[2.2.1]heptane 
• 77-95-2 D-(-)-quinic acid 
• 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 
• 123994-31-0 methyl (3S,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate 

Downstream Products

• 40980-53-8 (-)-gabosine C 
• 57449-31-7 (E)-But-2-enoic acid 2,3,5-triacetoxy-benzyl ester 
• 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 

Relevant academic research and scientific papers

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

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.

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.