73968-62-4

Usage

Uses

Used in Organic Synthesis:
(S)-(+)-GAMMA-(TRITYLOXYMETHYL)-GAMMA-BUTYROLACTONE is used as a protecting group in organic synthesis for alcohols, facilitating the selective reaction of other functional groups present in the molecule.
Used in Pharmaceutical Production:
In the Pharmaceutical Industry, (S)-(+)-GAMMA-(TRITYLOXYMETHYL)-GAMMA-BUTYROLACTONE is used as a building block for the synthesis of various pharmaceuticals, leveraging its properties as a precursor to GABA and its potential role in the development of new drugs.
Used in Solvent Applications:
(S)-(+)-GAMMA-(TRITYLOXYMETHYL)-GAMMA-BUTYROLACTONE is used as a solvent in chemical processes, taking advantage of its ability to dissolve a wide range of substances and facilitate reactions.
Used in the Synthesis of Fine Chemicals:
In the Chemical Industry, (S)-(+)-GAMMA-(TRITYLOXYMETHYL)-GAMMA-BUTYROLACTONE is utilized as a precursor in the synthesis of fine chemicals, contributing to the creation of specialty products with specific applications.

InChI:InChI=1/C24H22O3/c25-23-17-16-22(27-23)18-26-24(19-10-4-1-5-11-19,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-15,22H,16-18H2/t22-/m0/s1

Upstream product

• 56-86-0 L-glutamic acid 
• 149142-33-6 5-O-trityl-2-deoxy-D-erythro-pentono-1,5-lactone 
• 5336-08-3 D-Ribono-1,4-lactone 
• 34371-14-7 2-deoxy-D-ribonolactone 
• 20603-45-6 3,4-O-Benzylidene-D-(+)-ribonic acid δ-lactone 
• 146918-99-2 3,4-O-(R)-benzylidene-2-deoxy-D-erythro-ribono-1,5-lactone 
• 76-83-5 trityl chloride 
• 78508-96-0 (5S)-5-(hydroxymethyl)-5H-furan-2-one 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 76236-32-3 2,3-dideoxy-5-O-(triphenylmethyl)-D-glycero-pent-2-enono-1,4-lactone 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 

Downstream Products

• 75652-70-9 (+)-(3R,5S)-3-allyl-5-trityloxymethyltetrahydrofuran-2-one 
• 138772-44-8 (3R,5S)-3-((R)-1-Hydroxy-6-methyl-heptyl)-5-trityloxymethyl-dihydro-furan-2-one 
• 138772-43-7 (3R,5S)-3-((S)-1-Hydroxy-6-methyl-heptyl)-5-trityloxymethyl-dihydro-furan-2-one 
• 138772-41-5 (3S,5S)-3-((R)-1-Hydroxy-6-methyl-heptyl)-5-trityloxymethyl-dihydro-furan-2-one 
• 138772-42-6 (3S,5S)-3-((S)-1-Hydroxy-6-methyl-heptyl)-5-trityloxymethyl-dihydro-furan-2-one 
• 240400-98-0 (2S)-1-(trityloxy)-5-vinyl-6-heptene-2,5-diol 
• 101901-31-9 (3R,5S)-3-methyl-5-((trityloxy)methyl)dihydrofuran-2(3H)-one 
• 101901-32-0 (3S,5S)-3-methyl-5-((trityloxy)methyl)dihydrofuran-2(3H)-one 

Relevant academic research and scientific papers

Total Synthesis of Belizentrin Methyl Ester: Report on a Likely Conquest

The assigned structure of the dinoflagellate-derived toxin belizentrin was prepared by total synthesis in form of the corresponding methyl ester for stability reasons. The successful route features an unusual solution for the preparation of a recalcitrant ylide on a C-glycosidic segment; moreover, it involves an asymmetric hetero-Diels–Alder reaction en route to the tertiary hemiacetal substructure, a Negishi cross-coupling of two elaborate building blocks, and a macrocyclization based on an intramolecular aminolysis of a spirolactone. A modified Kocienski olefination ultimately allowed the polyol side chain to be attached to the macrocycle although this transformation faced the exceptional base sensitivity of this polyunsaturated target compound.

Elucidating the interaction of γ-hydroxymethyl-γ-butyrolactone substituents with model membranes and protein kinase C-C1 domains

The protein kinase C (PKC) family of proteins is an attractive drug target. Dysregulation of PKC-dependent signalling pathways is related to several human diseases like cancer, immunological and other diseases. We approached the problem of altering PKC activities by developing C1 domain-based PKC ligands. In this report γ-hydroxymethyl-γ-butyrolactone (HGL) substituents were investigated in an effort to develop small molecule-based PKC regulators with higher specificity for C1 domain than the endogenous diacylglycerols (DAGs). Extensive analysis of membrane-ligands interaction measurements revealed that the membrane-active compounds strongly interact with the lipid bilayers and the hydrophilic parts of compounds localize at the bilayer/water interface. The pharmacophores like hydroxymethyl, carbonyl groups and acyl-chain length of the compounds are crucial for their interaction with the C1 domain proteins. The potent compounds showed more than 17-fold stronger binding affinity for the C1 domains than DAG under similar experimental conditions. Nonradioactive kinase assay confirmed that these potent compounds have similar or better PKC dependent phosphorylation capabilities than DAG under similar experimental conditions. Hence, our findings reveal that these HGL analogues represent an attractive group of structurally simple C1 domain ligands that can be further structurally altered to improve their potencies.

Novel peptides comprising furanoid sugar amino acids for the treatment of cancer

Anticancer peptides which incorporate furanoid sugar amino acids and compositions made using these peptides are described. Methods for synthesis of the peptides and for preparing the furanoid sugar amino acids are disclosed. The peptides and compositions made using the peptides have pharmacological applications of these peptides especially in the treatment and prevention of cancer and tumors.

Conformational studies of 3,4-dideoxy furanoid sugar amino acid containing analogs of the receptor binding inhibitor of vasoactive intestinal peptide

Conformational analysis of vasoactive intestinal peptide (VIP) receptor binding inhibitor Leu1-Met2-Tyr3-Pro 4-Thr5-Tyr6-Leu7-Lys8 1 by various NMR techniques and constrained molecular dynamics (MD) simulation studies revealed that the molecule had a turn structure involving its Tyr 3-Pro4-Thr5-Tyr6 moiety with intramolecular hydrogen bond between Tyr6NH→Tyr3CO. In order to mimic the structure of 1, peptidomimetic analogs 2-4 were synthesized using conformationally constrained scaffolds of 3,4-dideoxy furanoid sugar amino acids (2S,5R)-ddSaa1 5 and its enantiomer (2R,5S)-ddSaa2 6. All these analogs displayed well defined three-dimensional structures akin to that found in 1. Peptides 2 and 3, which differed only in the sugar amino acid stereochemistry, show propensity of structures with identical intramolecular hydrogen bonds between ThrNH→MetCO. A similar structure with a hydrogen bond between TyrNH→MetCO was observed in 4. Graphical Abstract.

Enantioselective synthesis of key intermediates in a novel approach towards the Iboga-alkaloid family

Significant improvements in the realm of a recently disclosed, novel synthetic concept towards the Iboga alkaloid family are presented. The key step for the construction of the bicyclic aliphatic core consists of an intramolecular nitrone-olefin 1,3-dipolar cycloaddition reaction of a 1:1 mixture 15/16 yielding the two diastereoisomeric tricyclic isoxazolidine derivatives 17 and 18. The required nitrones were prepared from the readily available (S)-hydroxylactone 6 in twelve steps with an oyerall yield of 15% (average: 83.5% per step). The relative configuration of the minor isomer was deduced unambiguously by single-crystal X-ray analysis of the derived tricyclic carbamate 21. As four out of five asymmetric centers in the pair 17/18 have opposite configuration, destruction of the one possessing the same absolute configuration transforms the original set of diastereoisomers into a pair of enantiomers. We verified this contention by oxidizing the two alcohols 20 and 22 to yield the two antipodal forms of ketone 23. The absence of significant amounts of by-product and the high reproducibility of the crucial cycloaddition reaction represent marked improvements over our earlier attempts. In addition, the new route, which starts from L-glutamate, should provide access to both naturally occurring antipodal series of the targeted alkaloid class.

Phthalazine derivatives and remedies for erectile dysfunction

The present invention provides a phthalazine compound as a therapeutic agent for erectile dysfunction represented by the following formula, a pharmacologically acceptable salt thereof or a hydrate thereof: wherein R1and R2are the same as or different from each other and represent a halogen atom, a C1 to C4 alkyl group which may be substituted with a halogen atom, a C1 to C4 alkoxy group which may be substituted with a halogen atom or a cyano group; X represents a cyano group, a nitro group, a halogen atom, a hydroxyimino group which may be substituted or a heteroaryl group which may be substituted; Y represents a heteroaryl group, an aryl group which may be substituted, an alkynyl group which may substituted, an alkenyl group, an alkyl group, an optionally substituted saturated or unsaturated 4- to 8-membered amine ring, and the cyclic amine compound is a monocyclic compound, bicyclic compound or a spiro compound; l is an integer of 1 to 3; provided that the case where l is 1 or 2, X is a cyano group, a nitro group or a chlorine atom, R1is a chlorine atom, R2is a methoxy group and Y is a 5- or 6-membered amine ring substituted with a hydroxyl group is excluded.

Synthesis of (+)-muscarine from (S)-(-)-5-hydroxymethyl-2(5H)-furanone

(+)-Muscarine has been synthesized from (S)-(-)-5-hydroxy-2(5H)-furanone via rather a long pathway to provide easy access to a wide variety of its analogues. (C) 2000 Published by Elsevier Science Ltd.

An enantioselective ring expansion route leading to furanose and pyranose nucleosides featuring spirodiketopiperazines at the anomeric position

A study directed at the enantioselective synthesis of spirodiketopiperazine homologues of hydantocidin is described. Furanoid glycals, systems that are amenable to C-5 metalation in the presence of tert- butyllithium, are readily coupled to N-protected 2,3-azetidinediones provided that at least 1 equiv of BF3·OEt2 is present to curb enolization. The resulting 1:1 mixtures of carbinols undergo smooth ring expansion to spirocyclic keto amides when heated with pyridinium p-toluenesulfonate in benzene. 1,2-Acyl shifts operate exclusively. Since attempts to engage these products in Beckmann rearrangement proved singularly unsuccessful, recourse was alternatively made to new methodology based upon sequential Baeyer- Villiger oxidation and ammonolysis. The data show that the first of these steps occurs with exclusive migration of the quaternary carbon. Furthermore, nucleophilic attack by NH3 can be directed regioselectively to the anomeric region. If heating is supplied during acid-promoted cyclization to the spirodiketopiperazines, spiropyranose derivatives are produced in a complementary process. The central issue of this synthesis effort was the utilization of 4-phenylseleno-substituted furanoid glycals so as to ultimately enable introduction of the cis-diol functionality at C-3 and C-4 (hydantocidin numbering).

Chiral synthesis of (S)-(+)-γ-hydroxymethyl-γ-butyrolactone

S-(+)-γ-hydroxymethyl-γ-butyrolactone has been synthesized from D- ribonolactone as chiral template.

A ring-expansion route to analogues of dideoxyhydantocidin

The acid-catalyzed rearrangement of hydroxy β-lactam (12), formed by addition of the enantiopure dihydrofuranyllithium (10a) to N-benzyl-2,3-azetidinedione, has been investigated as a potential route to spirocyclic nucleosides.