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Tert-butyl (S)-2-hydroxy-2-phenylacetate, also known as (S)-tert-butyl 2-hydroxy-2-phenylacetate, is a chiral compound with the molecular formula C12H16O3. It is a derivative of 2-hydroxy-2-phenylacetic acid, featuring a tert-butyl group attached to the chiral center. This organic compound is characterized by its asymmetric carbon atom, which results in two enantiomers: (R) and (S). The (S)-enantiomer is the one being referred to here. It is a white crystalline solid and is used as a chiral building block in the synthesis of various pharmaceuticals and natural products. Its applications include the production of enantiomerically pure compounds, which are essential in the development of drugs with specific biological activities. The compound's stability, reactivity, and selectivity make it a valuable intermediate in organic synthesis.

4768-43-8

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4768-43-8 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 4768-43-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,7,6 and 8 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4768-43:
(6*4)+(5*7)+(4*6)+(3*8)+(2*4)+(1*3)=118
118 % 10 = 8
So 4768-43-8 is a valid CAS Registry Number.

4768-43-8Relevant academic research and scientific papers

METHODS AND COMPOSITIONS FOR PREVENTING OPIOID ABUSE

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Paragraph 0486; 0487, (2016/11/28)

Abuse-resistant opioid compounds, drug delivery systems, pharmaceutical compositions comprising an opioid covalently bound to a chemical moiety are provided. Methods of delivering an active ingredient to a subject and methods of preventing opioid abuse are also provided.

Chiral N,N′-dioxide-FeCl3 complex-catalyzed asymmetric intramolecular Cannizzaro reaction

Wu, Wangbin,Liu, Xiaohua,Zhang, Yuheng,Ji, Jie,Huang, Tianyu,Lin, Lili,Feng, Xiaoming

supporting information, p. 11646 - 11649 (2015/07/15)

An environmentally benign catalyst, the N,N′-dioxide-FeCl3 complex, has been developed for the asymmetric intramolecular Cannizzaro reaction. Aryl and alkyl glyoxal monohydrates were applied to obtain α-hydroxy acid esters with excellent results. Deuterium-label and control experiments shed light on the reaction mechanism.

Enantio- and chemoselective Br?nsted-acid/Mg(nBu) 2 catalysed reduction of α-keto esters with catecholborane

Enders, Dieter,St?ckel, Bianca A.,Rembiak, Andreas

supporting information, p. 4489 - 4491 (2014/04/17)

The first enantio- and chemoselective Br?nsted-acid catalysed reduction of α-keto esters with catecholborane has been developed. The α-hydroxy esters were obtained under mild reaction conditions in virtually quantitative yields and excellent enantioselectivities. With slight modifications both enantiomers can be obtained without any loss of selectivity. This journal is the Partner Organisations 2014.

A highly efficient and enantioselective intramolecular cannizzaro reaction under TOX/Cu(II) catalysis

Wang, Pan,Tao, Wen-Jie,Sun, Xiu-Li,Liao, Saihu,Tang, Yong

, p. 16849 - 16852 (2013/12/04)

An asymmetric intramolecular Cannizzaro reaction of aryl and alkyl glyoxals with alcohols has been realized with an unprecedented high level of enantioselectivity, on the basis of a newly developed congested TOX ligand and a gradual liberation protocol of active glyoxals from glyoxal monohydrates. Preliminary results suggested a mechanism of enantioselective addition of alcohols to glyoxals contributing most to the stereoselectivity, other than by the dynamic kinetic resolution of hemiacetal intermediates.

Asymmetric addition of arylboronic acids to glyoxylate catalyzed by a ruthenium/Me-BIPAM complex

Yamamoto, Yasunori,Shirai, Tomohiko,Miyaura, Norio

, p. 2803 - 2805 (2012/04/23)

The enantioselective synthesis of α-hydroxy esters by ruthenium-catalyzed 1,2-addition of arylboronic acids to tert-butyl glyoxylate is described. The use of RuCl2(PPh3)3 with (R,R)-Me-BIPAM gave optically active mandelic acids of up to 99% ee. Addition of a fluoride salt such as potassium fluoride (KF) or caesium fluoride (CsF) was effective for achieving high enantioselectivities. The Royal Society of Chemistry 2012.

Stereomodulating effect of remote groups on the NADH-mimetic reduction of alkyl aroylformates with 1,4-dihydronicotinamide-β-lactam amides

Aizpurua, Jesus M.,Palomo, Claudio,Fratila, Raluca M.,Ferrón, Pablo,Miranda, José I.

experimental part, p. 3187 - 3194 (2010/06/12)

Conformationally restricted NADH peptidomimetics 4a-e, characterized by the presence of a (1,4-dihydronicotinamide)-(β-lactam) moiety, have been synthesized and used to study the Mg2+ cation-promoted asymmetric reduction of alkyl aroylformates

Chiral cobalt-catalyzed enantioselective aerobic oxidation of α-hydroxy esters

Alamsetti, Santosh Kumar,Sekar, Govindasamy

supporting information; experimental part, p. 7235 - 7237 (2010/12/24)

A chiral cobalt-catalyzed enantioselective aerobic oxidative kinetic resolution of (±)-α-hydroxy esters, using molecular oxygen as a sole oxidant, is reported and a maximum of selectivity factor (s) 31.9 was achieved with >99% enantiomeric excess for unreacted α-hydroxy esters.

Efficient preparation of aminoxyacyl amides, aminoxy hybrid peptides, and α-aminoxy peptides

Katritzky, Alan R.,Avan, Ilker,Tala, Srinivasa R.

supporting information; experimental part, p. 8690 - 8694 (2010/01/16)

(Chemical Equation Presented) N-(Pg-α-aminoxy acids) 1a-g are converted to N-(Pg-α-aminoxyacyl)benzotriazoles 2a-g, which react under mild conditions with amines, α-amino acids/α-dipeptides, and α-aminoxy acids to give aminoxyacyl amides 3a-g, (3e+3e′), and (3g+3g′), aminoxy hybrid peptides 4a-h, (4a+4a′), 6a-d, 9a-e, (9a+9a′), and (9b+9b′), and α-aminoxy peptides 10a,b in good yields without racemization. 2009 American Chemical Society.

3-Pyrroline-1-carbonyl (Pyroc) group: A removable protecting group for the kinetic resolution of racemic carboxylic acids and alcohols through catalytic asymmetric acylation

Sakakura, Akira,Umemura, Shuhei,Ishihara, Kazuaki

body text, p. 1647 - 1650 (2009/12/03)

The O-3-pyrroline-1-carbonyl (O-Pyroc) group and 3-pyrrolinamide are useful removable protecting groups for the kinetic resolution of racemic α-hydroxycarboxylic acids, β-hydroxycarboxylic acids, 1,2-dicarboxylic acids, and 1,2-diols using the L-histidine

Steric and electronic effects in the enantioselective hydrogenation of activated ketones on platinum: Directing effect of ester group

Diezi, Simon,Reimann, Sven,Bonalumi,Mallat, Tamas,Baiker, Alfons

, p. 255 - 262 (2007/10/03)

Steric effects in the Pt-catalyzed asymmetric hydrogenation of nine different α-ketoesters were studied by variation of the bulkiness at the keto and ester side of the substrates, and by using cinchonidine (CD), its 6′-methoxy derivative quinine, and o-ph

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