208720-47-2

Basic information

• Product Name: methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate
• Synonyms: methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate
• CAS NO: 208720-47-2
• Molecular Weight: 266.272
• Mol File: 208720-47-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate(208720-47-2)
• EPA Substance Registry System: methyl (3S,4R,5R)-3,4-dihydroxy-5-(mesyloxy)cyclohex-1-ene-1-carboxylate(208720-47-2)

Safety Data

• Hazardous Substances Data: 208720-47-2(Hazardous Substances Data)

Upstream product

• 88165-26-8 methyl 3,4-O-isopropylideneshikimate 
• 138-59-0 shikimic acid 
• 91758-24-6 Methyl (3R,4S,5R)-5-Hydroxy-3,4-<(methoxymethylene)dioxy>cyclohex-1-ene-1-carboxylate 
• 1422466-67-8 (3R,4S,5R)-methyl 5-methanesulfonyloxy-3,4-O-thionylshikimate 
• 352533-24-5 (3R,4S,5R)-methyl 3,4-O-thionylshikimate 
• 40983-58-2 methyl shikimate 

Downstream Products

• 1422466-68-9 (3R,4S,5R)-methyl 4-hydroxy-5-methanesulfonyloxy-3-tosyloxycyclohex-1-enecarboxylate 
• 135292-62-5 methyl (3R,4S,5R)-5-azido-3,4-dihydroxycyclohex-1-ene-1-carboxylate 
• 208720-77-8 (3R,4R,5S)-4-Amino-5-azido-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester 
• 208589-18-8 (3R,4R,5S)-4-Acetylamino-5-amino-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester 
• 187226-68-2 (3R,4R,5S)-4-Acetylamino-5-azido-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester 
• 208589-19-9 (3R,4R,5S)-4-acetamido-5-(N²,N³-bis(tert-butoxycarbonyl)guanidino)-3-propoxy-1-cyclohexene-1-carboxylic acid 
• 208720-57-4 C₂₃H₃₈N₄O₈ 

Relevant articles and documents

Targeting the Motion of Shikimate Kinase: Development of Competitive Inhibitors that Stabilize an Inactive Open Conformation of the Enzyme

The large conformational changes observed by Molecular Dynamics simulation studies on the product release in the LID and shikimic acid binding (SB) domains of the shikimate kinase (SK) enzyme have been exploited in the development of reversible competitive inhibitors against SK from Mycobacterium tuberculosis and Helicobacter pylori. This enzyme is a recognized target for antibiotic drug discovery. The reported C5-substituted shikimic acid analogues interact with the dynamic apolar pocket that surrounds the C4 and C5 hydroxyl groups of the natural substrate, cause the opening of the LID and SB domains, and capture the essential arginine far from the ATP binding site as required for catalysis. The 3-nitrobenzyl 3e and 5-benzothiophenyl derivatives 3i proved to be the most potent inhibitors. An ester prodrug of 3i was the most efficient derivative in achieving good in vitro activity against H. pylori, having a MIC value of 4 μg/mL.

Novel and efficient syntheses of four useful shikimate-derived epoxy chiral building blocks via cyclic sulfite intermediates

All of the four stereoisomers of methyl 4,5-epoxy-3-hydroxy-cyclohex-1-ene- carboxylate (1a-1d) are useful chiral building blocks. Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abundant (-)-shikimic acid (2) via c