15271-51-9

Basic information

• Product Name: (+/-)-shikimic acid
• Synonyms: (+/-)-shikimic acid
• CAS NO: 15271-51-9
• Molecular Weight: 174.153
• Mol File: 15271-51-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (+/-)-shikimic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-shikimic acid(15271-51-9)
• EPA Substance Registry System: (+/-)-shikimic acid(15271-51-9)

Safety Data

• Hazardous Substances Data: 15271-51-9(Hazardous Substances Data)

Upstream product

• 1476028-68-8 (3R,4S,5R)-ethyl 3,4-epoxy-5-hydroxycyclohex-1-ene-1-carboxylate 
• 21654-28-4 (+/-)-7c-acetoxy-2,2-dimethyl-(3ar,7ac)-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 131928-05-7 (1R,2S,5S)-2-Acetoxy-5-(dimethyl-phenyl-silanyl)-cyclohex-3-enecarboxylic acid 2-trimethylsilanyl-ethyl ester 
• 17791-32-1 7-Oxabicyclo<2.2.1>hept-5-en-2-carbonsaeure-methylester 
• 16613-45-9 (+/-)-methyl triacetylshikimate 
• 131928-07-9 (3S,4R,5S)-3,4,5-Trihydroxy-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester 
• 4372-89-8 (+/-)-methyl shikimate 
• 261631-95-2 (-)-(1S)-1-{(4S,5S)-5-[(1S)-1-hydroxy-2-propenyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-propen-1-ol 
• 1121652-18-3 (3aS,5aS,6aS,6bS)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno-[2′,3′:3,4]benzo[1,2-d][1,3]dioxole 
• 1583240-50-9 (3aR,4S,5aR,6aR,6bS)-2,2-dimethylhexahydrooxireno[2′,3′:3,4]-benzo[1,2-d][1,3]dioxol-4-ol 
• 145107-27-3 (3aR,5aR,6aR,6bR)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno-[2′,3′:3,4]benzo[1,2-d][1,3]dioxole 
• 1582805-94-4 (1R,2R,3S,4S)-1-chloro-2-acetoxy-3,4-(isopropylidenedioxy)-cyclohex-5-ene 
• 88517-54-8 (1S,2S,6R,7R)-4,4-Dimethyl-3,5,10-trioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid methyl ester 
• 88517-53-7 cis-exo-2,3-dihydroxy-6-methoxycarbonyl-7-oxabicycloheptane 

Relevant articles and documents

A C 2-symmetric chiral pool-based flexible strategy: Synthesis of (+)- and (-)-shikimic acids, (+)- and (-)-4- epi -shikimic acids, and (+)- and (-)-pinitol

Via combination of a novel acid-promoted rearrangement of acetal functionality with the controlled installation of the epoxide unit to create the pivotal epoxide intermediates in enantiomerically pure form, a simple, concise, flexible, and readily scalable enantiodivergent synthesis of (+)- and (-)-shikimic acids and (+)- and (-)-4-epi-shikimic acids has emerged. This simple strategy not only provides an efficient approach to shikimic acids but also can readily be adopted for the synthesis of (+)- and (-)-pinitols. These concise total syntheses exemplify the use of pivotal allylic epoxide 14 and its enantiomer ent-14. A readily available inexpensive C2-symmetric l-tartaric acid (7) served as key precursor. In general, the strategy here provides a neat example of the use of a four-carbon chiron and offers a good account of the synthesis of functionalized cyclohexane targets.

(1E,3E)-4-acetoxy-1-phenyldimethylsilyl-1,3-butadiene as a surrogate for (1E,3E)-1,4-diacetoxy-1,3-butadiene: A highly coefficient synthesis of (±)-shikimic acid

The 5-step synthesis of (±)-shikimic acid has been achieved in 55% overall yield from (1E,3E)-4-acetoxy-1-phenyldimethylsilyl-1,3-butadiene, starting with its Diels-Alder reaction with 2-(trimethylsilyl)ethyl acrylate and featuring the use of Fleming's on

SHIKIMIC ACIDS FROM FURAN; METHODS OF STEREOCONTROLLED ACCESS TO 3,4,5-TRIOXIGENATED CYCLOHEXENES

Oxabicycloheptenes 1 and 2 are converted to 3,4,5-oxigenated cyclohexenes by stereocontrolled hydroxylations and epoxidations coupled with reverse-Michael cleavage of the oxabicyclo system.Three epimers of shikimic acid are synthesized by these methods.