191403-66-4

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-Benzyl-4-hydroxy-2-pyrrolidinone is used as a key intermediate for the synthesis of various pharmaceuticals and biologically active compounds. Its chiral nature and synthetic versatility make it a valuable building block in the development of new drugs and therapeutic agents.
Used in Biotechnological Applications:
(S)-1-Benzyl-4-hydroxy-2-pyrrolidinone can be biosynthesized using recombinant E. coli expressing P450pyr Monooxygenase. This method allows for the production of the compound in a more sustainable and environmentally friendly manner, as it utilizes biological processes rather than traditional chemical synthesis.

InChI:InChI=1/C11H13NO2/c13-10-6-11(14)12(8-10)7-9-4-2-1-3-5-9/h1-5,10,13H,6-8H2/t10-/m0/s1

Upstream product

• 67-56-1 methanol 
• 253608-06-9 (4S,5R)-1-benzyl-4-hydroxy-5-thiophenol-2-pyrrolidinone 
• 74-88-4 methyl iodide 
• 67-64-1 acetone 
• 186428-91-1 (S)-N-benzyl-4-tert-butyldimethylsilyloxy-pyrrolidin-2-one 
• 100-46-9 benzylamine 
• 100-39-0 benzyl bromide 
• 1431373-89-5 (S)-4-(benzyl-benzyloxycarbonyl-amino)-3-benzyloxy-butyric acid 
• 129823-21-8 (S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione 
• 132917-66-9 acetic acid (2S,3S)-1-benzyl-2-hydroxy-5-oxo-pyrrolidin-3-yl ester 
• 5291-77-0 1-benzyl-2-pyrrolidone 
• 123-11-5 4-methoxy-benzaldehyde 
• 108-94-1 cyclohexanone 
• 100-52-7 benzaldehyde 

Downstream Products

• 101385-90-4 (S)-N-benzyl-3-hydroxypyrrolidine 
• 913566-62-8 (S)-1-benzyl-4-(a-diazoacetoxy)pyrrolidin-2-one 
• 68108-18-9 (4S)-4-hydroxypyrrolidin-2-one 

Relevant academic research and scientific papers

Synthesis of nature product kinsenoside analogues with anti-inflammatory activity

Kinsenoside is the major bioactive component from herbal medicine with a broad range of pharmacological functions. Goodyeroside A, an epimer of kinsenoside, remains less explored. In this report we chemically synthesized kinsenoside, goodyeroside A and their analogues with glycan variation, chirality inversion at chiral center(s), and bioisosteric replacement of lactone with lactam. Among these compounds, goodyeroside A and its mannosyl counterpart demonstrated superior anti-inflammatory efficacy. Furthermore, goodyeroside A was found to suppresses inflammatory through inhibiting NF-κB signal pathway, effectively. Structure-activity relationship is also explored for further development of more promising kinsenoside analogues as drug candidates.

Gamma-lactam glycoside derivative, and synthesis method and application thereof

The invention relates to a gamma-lactam glycoside derivative, and a synthesis method and application thereof. The structure of the formula I is shown as follows (please see the specification for the formula I), wherein R is selected from a beta-D-glucopyranose group, an alpha-D-glucopyranose group, a beta-D-galactopyranose group, an alpha-D-galactopyranose group, a beta-D-mannopyranose group, an alpha-D-mannopyranose grop, a beta-D-xylopyranose group, an alpha-D-xylopyranose group, a beta-L-pyran rhamnose group and an alpha-L-pyran rhamnose group, and the bond shown in the specification represents pointing to the page or the bond shown in the specification represents pointing out of the page.

Method (S)-3- for -1- synthesizing P-hydroxymethylbenzopyrrolidine (by machine translation)

After the completion of (S)- 3 - the dropwise addition of the solvent, the reaction liquid,S1, drops are added, into the solvent and then, refluxed, under the (S)- 3, conditions of the temperature under, the conditions 20-65 °C of, the. temperature of the temperature 4 - of the temperature of the reflux ;S2, of (S)4 - the reaction solution, 10-65 °C 10-12h;S3, (S)- 1 -S4, (S)- 1 - 0-65 °C 12-20h;S5, (S)- 3 . (by machine translation)

Stereoselective synthesis of (S)-oxiracetam and (S)-GABOB from (R)-glyceraldehyde acetonide

Synthetic routes to (S)-oxiracetam and (S)-GABOB have been developed starting from (R)-glyceraldehyde acetonide through its conversion to an appropriate aldehyde intermediate followed by reductive amination using glycinamide hydrochloride/benzyl amine and subsequent chemical transformations.

Regio- and stereoselective biohydroxylations with a recombinant escherichia coli expressing P450pyr monooxygenase of sphingomonas Sp. HXN-200

A recombinant Escherichia coli expressing P450pyr monooxygenase of Sphingomonas sp. HXN-200 was developed as a useful biocatalyst for regio- and stereoselective hydroxylations, with no side reaction and easy cell growth. The resting E. coli cells showed an activity of 4.1 U/g cdw and 9.9 U/g cdw for the hydroxylation of N-benzylpyrrolidin-2-one 1 and N-benzyloxycarbonylpyrrolidine 3, respectively, being as active as the wide-type strain. Biohydroxylation of N-benzylpyrrolidin-2-one 1 with the resting cells gave (S)-N-benzyl-4- hydroxypyrrolidin-2-one 2 in >99% ee and 10.8 mM, a 2.6 times increase of product concentration in comparison with the wild-type strain. Biohydroxylation of N-tert-butoxycarbonylpiperidin-2-one 5, N-benzylpiperidine 7 and N-tert-butoxycarbonylazetidine 9 with the E. coli cells afforded the corresponding 4-hydroxypiperidin-2-one 6, 4-hydroxypiperidine 8, and 3-hydroxyazetidine 10 in 14 mM, 17 mM, and 21 mM, respectively. Moreover, hydroxylation of (-)-β-pinene 11 with the recombinant E. coli cells showed excellent regio- and stereoselectivity and gave (1R)-trans-pinocarveol 12 in 82% yield and 4.1 mM, which is over 200 times higher than that obtained with the best biocatalytic system known thus far. The recombinant strain was also able to hydroxylate other types of substrates with unique selectivity: biohydroxylation of norbornane 13 gave exo-norbornaeol 14, with exo/endo selectivity of 95%; tetralin 15 and 6-methoxytetralin 17 were hydroxylated at the non-activated 2-position, for the first time, with regioselectivities of 83-84%. Copyright

Nonracemic bicyclic lactam lactones via regio- and cis-diastereocontrolled C-H insertion. Asymmetric synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol

(Chemical Equation Presented) The Rh2(MPPIM)4- catalyzed intramolecular C-H insertion reaction of (S)- and (R)-1-benzyl-5-(R- diazoacetoxy)piperidin-2-one and (S)-1-benzyl-4-(α-diazoacetoxy) pyrrolidin-2-one proceeds with high regios

Regio- and diastereocontrolled C-H insertion of chiral γ- and δ-lactam diazoacetates. Application to the asymmetric synthesis of (8S,8aS)-8-hydroxyindolizidine

γ- and δ-Lactam diazoacetates undergo efficient intramolecular C-H insertion catalyzed by Rh2(MPPIM)4 with excellent regioselectivity and cis-diastereoselectivity to provide synthetically useful bicyclic lactam lactones. The Royal So

Preparation of (S)-N-Substituted 4-Hydroxy-pyrrolidin-2-ones by Regio- and Stereoselective Hydroxylation with Sphingomonas sp. HXN-200

formula presented Enantiopure (S)-N-substituted 4-hydroxy-pyrrolidin-2-ones have been prepared for the first time by regio- and stereoselective hydroxylation of the corresponding pyrrolidin-2-ones by use of a biocatalyst. Hydroxylation of 6 and 8 with Sph

A new approach to (S)-4-hydroxy-2-pyrrolidinone and its 3-substituted analogues

Successive treatment of a phenyl thioether derived from (S)-malic acid with n-BuLi, lithium naphthalenide (LN), and electrophiles led to 4-hydroxy- 3-substituted 2-pyrrolidinones in one-pot and in high regio- and diastereoselectivity at C-3. N-Debenzylation of 1-benzyl-4-hydroxy-2- pyrrolidinone using LN afforded naturally occurring (-)-(S)-4-hydroxy-2- pyrrolidinone. (-)-(3S,4S)-4-Hydroxy-3-methyl-2-pyrrolidinone, the lactam form of the γ-amino acid residue found in marine natural products, bistramides, was prepared by the same method.