40983-58-2

Basic information

• Product Name: METHYL (-)-SHIKIMATE
• Synonyms: METHYL (-)-SHIKIMATE;Nsc280656
• CAS NO: 40983-58-2
• Molecular Formula: C₈H₁₂O₅
• Molecular Weight: 188.17788
• Product Categories: Chiral Reagents
• Mol File: 40983-58-2.mol
• Article Data: 65

Chemical Properties

• Melting Point: 114-115°C
• Boiling Point: 317.3°Cat760mmHg
• Flash Point: 127.7°C
• Appearance: /
• Density: 1.489g/cm³
• Vapor Pressure: 3.25E-05mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Very Slightly, Heated), Methanol (Slightly)
• PKA: 13.48±0.70(Predicted)
• CAS DataBase Reference: METHYL (-)-SHIKIMATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (-)-SHIKIMATE(40983-58-2)
• EPA Substance Registry System: METHYL (-)-SHIKIMATE(40983-58-2)

Safety Data

• Hazardous Substances Data: 40983-58-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

A common biosynthetic precursor

InChI:InChI=1/C8H12O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2,5-7,9-11H,3H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 138-59-0 shikimic acid 
• 17515-18-3 (3R,4S,5R)-methyl 3,4,5-triacetoxy-1-cyclohexene-1-carboxylate (methyl (-)-shikimate triacetate) 
• 113473-07-7 (1R,2S,3R,4S,5R)-2,3,4,5-Tetraacetoxy-cyclohexanecarboxylic acid methyl ester 
• 143308-74-1 (3aR,7R,7aS)-methyl 7-acetoxy-2,2-dimethyl-3a,6,7,7atetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 245054-34-6 methyl (3R,4S,5R)-3-benzoyloxy-4,5-dihydroxy-cyclohex-1-en-1-carboxylate 
• 67-56-1 methanol 
• 78844-86-7 rac-(1R,5R,6S)-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-en-5-ol 
• 88517-55-9 (+/-)-methyl 5,6-O,O-isopropylidinecyclohexa-1,3-diene-2-carboxylate 
• 88165-26-8 methyl 3α,4α-isopropylidenedioxy-5β-hydroxycyclohex-1-ene-1-carboxylate 
• 83604-10-8 (R)-5-Hydroxy-cyclohexa-1,3-dienecarboxylic acid methyl ester 
• 245054-33-5 methyl (3R,4S,5R)-3-benzoyloxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate 
• 245054-31-3 (2S,3S,4aR,8S,8aR)-methyl 8-hydroxy-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate 
• 245054-30-2 methyl (4S,5R)-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-3-oxo-cyclohex-1-en-1-carboxylate 

Downstream Products

• 138-59-0 shikimic acid 
• 138-59-0 +/-5-epishikimic acid 
• 4114-28-7 diethyl hydrazodicarboxylate 
• 76985-84-7 (-)-methyl cis-3-hydroxy-4,5-oxycyclohex-1-enecarboxylate 
• 6973-02-0 (3R)-3r,4c,5t-trihydroxy-cyclohexane-c-carboxylic acid methyl ester 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 143615-30-9 methyl 4-O-acetylshikimate 
• 352533-29-0 methyl (3S,4R,5R)-5-acetoxy-3-azido-4-hydroxycyclohex-1-ene-1-carboxylate 
• 96251-70-6 compound Z₁ 
• 1257516-56-5 C₁₀H₁₄O₆ 
• 1257516-57-6 C₁₀H₁₄O₆ 
• 139356-35-7 3,5-di-(tert-butyl-dimethylsilyloxy)-(3S,5S)-cyclohexan-1-one 
• 139356-37-9 [(3R,5R)-3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidene]-ethanol 
• 139356-38-0 ((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane) 

Relevant articles and documents

Gram-scale carbasugar synthesis: Via intramolecular seleno -Michael/aldol reaction

Carbasugars represent an important category of natural products possessing a broad spectrum of biological activities. Lots of effort has been done to develop gram scale synthesis. We are presenting a new approach to gram scale synthesis of the carbasugar skeleton via intramolecular seleno-Michael/aldol reaction. The proposed strategy gave gram amounts of 6-hydroxy shikimic ester in a tandem process in 36% overall yield starting from d-lyxose. We have attempted to demonstrate the synthetic utility of 6-hydroxyshikimic acid derivatives by covering the important synthetic modifications and related applications, namely synthesis of protected (-)-gabosine E, (-)-MK7606, (-)-valienamine and finally unprotected methyl (-)-shikimate.

Deoxy-nitrosugars. Synthesis of Methyl Shikimate and of Diethyl Phosphashikimate from D-Ribose

The chain elongation of the deoxy-nitroribose 6 by a Michael addition to the vinylphosphonate 7 followed by a solvolysis gave the heptulosephosphonate 11 (87percent).From 11, the key intermediates 15 and 16 (77percent) were obtained by a highly diastereos

Synthesis of (6S)-6-fluoroshikimic acid

(6S)-6-Fluoroshikimic acid 2 and (6R)-6-hydroxyshikimic acid 16 have been synthesised via an OsO4-catalysed dihydroxylation of diene 8, which was derived from (-)-shikimic acid 1.

An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach to Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray

The anal secretions of skunks comprise several types of malodorous organosulfur compounds. The pungent metabolites are used defensively by skunks to repel threats posed by predators, and in many parts of the world, those perceived threats include humans a

Economical Process for Preparation of the 19-nor A Ring of Paricalcitol from (-)-Shikimic Acid

An economical and efficient means of preparing the 19-nor A ring, a key precursor of the vitamin D receptor (VDR) activator Paricalcitol, is here described. This process begins with commercially available (-)-shikimic acid and was easily scaled up to kilo