236751-52-3

Upstream product

• 236751-84-1 (1S,4S,5R)-4,N-(dibenzyloxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one 
• 100-51-6 benzyl alcohol 
• 773143-71-8 (3aS,4R,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile 
• 254441-93-5 (3R,4R,5R)-3,4-O-isopropylidene-5-cyano-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 254441-94-6 (3R,4R,5S)-3,4-O-isopropylidene-5-cyano-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 773143-72-9 (3aS,4S,6aS)-5-(4-Methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonitrile 
• 98-79-3 L-Pyroglutamic acid 
• 500759-36-4 (3S,4R,5S)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 500759-35-3 (3S,4R,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 370839-88-6 (3R,4S,5S)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 370839-89-7 (3R,4S,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-cyano-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 236751-80-7 benzyl 2,3-aziridino-N-(benzyloxycarbonyl)-2,3-dideoxy-β-D-lyxofuranuronate 
• 773143-70-7 Acetic acid (3S,4S)-4-acetoxy-2-cyano-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-3-yl ester 

Relevant academic research and scientific papers

First enantiospecific synthesis of a 3,4-dihydroxy-L-glutamic acid [(3S,4S)-DHGA], a new mGluR1 agonist

The first synthesis of one of the 4 possible stereoisomers of 3,4- dihydroxy-L-glutamic acid ((3S,4S)-DHGA 3), a natural product of unknown configuration, is described. The synthesis is based on the Lewis acid catalyzed reaction of benzyl alcohol with a D

Asymmetric synthesis of 3,4-dihydroxyglutamic acids via enantioselective reduction of cyclic meso-imide

Stereoselective synthesis of (3S,4S)- and (3R,4R)-series of 3,4-dihydroxyglutamic acids was investigated. The key reaction in this synthesis is asymmetric reduction of meso-imide derived from meso-tartaric acid. Lewis acid-promoted cyanation of the obtained optically active lactam via the acyliminium intermediate followed by standard deprotection procedure afforded the desired 3,4-dihydroxyglutamic acids. Graphical abstract

Synthesis and reactions of a novel 3,4-didehydropyroglutamate derivative

Some reactions such as catalytic hydrogenation, Diels-Alder reaction, cyclopropanation, dihydroxylation, and Michael addition of a novel 3,4-didehydropyroglutamate derivative, in which the carboxylic group is protected as an ABO ester, are examined and found to take place in a stereospecific manner giving 3- and/or 4-substituted pyroglutamate derivatives without loss of enantiomeric purity at the α-position.

A concise approach to homochiral 3,4-dihydroxyglutamic acids

A concise diastereoselective synthesis of 3,4-dihydroxyglutamic acids was investigated. The key reaction in this synthesis is stereoselective cyanation of an optically active N-acyliminium intermediate derived from L- or D-tartaric acid. The stereoselectivity in the cyanation reaction could be controlled by the protective group of the hydroxyl function. Deprotection of the obtained cyanolactam followed by acidic hydrolysis afforded the desired 3,4-dihydroxyglutamic acids. The 3,4-dihydroxyglutamic acids obtained in this synthesis are (2S,3S,4R)-, (2R,3S,4R)-, (2S,3R,4S)-, and (2R,3R,4S)-isomers and the three latter compounds are novel derivatives of glutamic acids.

A concise diastereoselective synthesis of (2S,3S,4R)-3,4-dihydroxyglutamic acid

A concise diastereoselective synthesis of (2S,3S,4R)-3,4-dihydroxyglutamic acid, one of eight possible stereoisomers of 3,4-dihydroxyglutamic acids, is described. The key reaction in this synthesis is stereoselective cyanation of an optically active N-acyliminium intermediate derived from L-tartaric acid with tributyltin cyanide.

A new straightforward synthesis of 2,3-aziridino-γ-lactones

A concise synthesis of 2,3-aziridino-γ-lactones starting from commercially available α,β-dihydroxy-γ-lactones is described. The strategy involves a Michael-type addition of benzylamine onto a key 2-(5H)-furanon-3-yl trifluoromethanesulfonate, followed by in situ cyclization to the aziridine without lactone-ring-opening. (C) 2000 Elsevier Science Ltd.

Application of 2,3-aziridino-γ-lactone methodology toward the enantiospecific synthesis of the (3S,4S)-isomer of dihydroxy-L-glutamic acid

The formal synthesis of benzyl 2,3-aziridino-N-(benzyloxycarbonyl)-2,3- dideoxy-γ-butyrolactone (21) from D-ribose is described. Reaction of 21 with excess benzyl alcohol in the presence of boron trifluoride etherate and hydrogenolysis of the product gave

Alpha hydroxyacids, alpha ketoacids and their use in treating skin conditions

Preventive as well as therapeutic treatment to alleviate the symptoms of skin disorders associated with disturbed keratinization or inflammation with one or more alpha or beta hydroxy-acids and alpha or beta ketoacids is disclosed. The alpha or beta hydroxyacids and alpha or beta ketoacids of this invention include free acids, or peroxide, amide, lactone, anhydride, ester, polymer, organic or inorganic salt forms thereof. Therapeutic compositions of this invention may include one or more of the alpha or beta hydroxyacids or the alpha or beta ketoacids of this invention present in a total amount of from 0.1 to 40 percent in an acceptable vehicle. The compositions are particularly useful for the topical treatment of skin conditions such as dry skin, ichthyosis, palmar and plantar hyperkeratosis, dandruff, Darier's disease, lichen simplex chronicus, keratoses, acne, psoriasis, eczema, pruritus and possibly warts and herpes.