78158-90-4

Basic information

• Product Name: R(-)-DIHYDRO-5-TRITYLOXYMETHYL-2(3H)-FURANONE
• Synonyms: R(-)-GAMMA-TRITYLOXYMETHYL-GAMMA-BUTYROLACTONE;R(-)-DIHYDRO-5-TRITYLOXYMETHYL-2(3H)-FURANONE;(R)-(-)-G-TRITYLOXYMETHYL-G-BUTYROLACTONE;5-O-TRITYL-2,3-DIDEOXY-L-GLYCEROPENTONO-1,4-LACTONE;(R)-(-)-G-TRITYLOXYMETHYL-G-BUTYROLACTONE 98+%;2(3H)-Furanone, dihydro-5-(triphenylmethoxy)methyl-, (5R)-;(r)-(-)-γ-trityloxymethyl-γ-butyrolactone;5-O-Trityl-2,3-dideoxy-L-glyceropentono-1,4-lactone, (R)-(-)-Dihydro-5-trityloxymethyl-2(3H)-furanone
• CAS NO: 78158-90-4
• Molecular Formula: C₂₄H₂₂O₃
• Molecular Weight: 358.43
• Mol File: 78158-90-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 150-152 °C(lit.)
• Boiling Point: 512.1°C at 760 mmHg
• Flash Point: 222.1°C
• Appearance: /
• Density: 1.163g/cm³
• Vapor Pressure: 1.33E-10mmHg at 25°C
• Refractive Index: 1.591
• BRN: 4911276
• CAS DataBase Reference: R(-)-DIHYDRO-5-TRITYLOXYMETHYL-2(3H)-FURANONE(CAS DataBase Reference)
• NIST Chemistry Reference: R(-)-DIHYDRO-5-TRITYLOXYMETHYL-2(3H)-FURANONE(78158-90-4)
• EPA Substance Registry System: R(-)-DIHYDRO-5-TRITYLOXYMETHYL-2(3H)-FURANONE(78158-90-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 78158-90-4(Hazardous Substances Data)

Usage

Description

R(-)-DIHYDRO-5-TRITYLOXYMETHYL-2(3H)-FURANONE is a chiral organic compound characterized by its unique trityl ether and furanone functional groups. It is a versatile building block in organic synthesis and has potential applications in various fields due to its distinct stereochemistry and reactivity.

Uses

Used in Pharmaceutical Industry:
R(-)-DIHYDRO-5-TRITYLOXYMETHYL-2(3H)-FURANONE is used as a key intermediate in the synthesis of biologically active compounds, particularly for the development of novel drugs targeting specific receptors or enzymes. Its unique structure allows for the creation of chiral molecules with potential therapeutic benefits.
Used in Chemical Research:
R(-)-DIHYDRO-5-TRITYLOXYMETHYL-2(3H)-FURANONE is used as a research tool in the study of stereoselective reactions and the development of new synthetic methodologies. Its reactivity and structural features make it an attractive candidate for exploring new reaction pathways and improving synthetic efficiency.
Used in Synthesis of Pentonolactones:
R(-)-DIHYDRO-5-TRITYLOXYMETHYL-2(3H)-FURANONE is used as a precursor in the synthesis of target pentonolactones for interaction studies of γ-lactones with the phorbol ester receptor of protein kinase. This application highlights its potential in the development of bioactive molecules with specific binding properties, which can be crucial for understanding and modulating biological processes.

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-/m1/s1

Upstream product

• 76-83-5 trityl chloride 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 6893-26-1 D-Glutamic acid 
• 53558-93-3 (R)-tetrahydro-5-oxo-2-furancarboxylic acid 
• 52813-63-5 (5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone 
• 73968-62-4 (5S)-5-[(trityloxy)methyl]tetrahydro-2-furanone 
• 78158-89-1 (S)-(+)-4-Hydroxy-5-trityloxypentanoic acid 

Downstream Products

• 666238-73-9 methyl [(2-R)-2,3,4,5-tetrahydro-5-oxo-2-furylmethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosid]uronate 
• 112945-21-8 amphidinolide C 
• 264921-76-8 2(R)-methyl-(R)-(-)-γ-trityloxymethyl-γ-butyrolactone 
• 139594-87-9 amphidinolide F 
• 1493781-31-9 C₂₉H₄₃F₃O₈Si 
• 1493781-30-8 C₂₉H₄₃F₃O₈Si 
• 1493781-25-1 C₂₉H₃₂O₄ 
• 148553-57-5 2,4-dimethoxy-(2'R)-trans-5-<2',5'-dihydro-5'-<(triphenylmethoxy)methyl>-2'-furanyl>pyrimidine 
• 148441-01-4 2,4-dimethoxy-(2'R)-5-<2',3'-dihydro-5'-<(triphenylmethoxy)methyl>-2'-furanyl>pyrimidine 
• 148440-97-5 (5R)-4,5-Dihydro-5-<(triphenylmethoxy)methyl>furan 

Relevant articles and documents

Concise total syntheses of amphidinolides C and F

The marine natural products amphidinolide C (1) and F (4) differ in their side chains but share a common macrolide core with a signature 1,4-diketone substructure. This particular motif inspired a synthesis plan predicating a late-stage formation of this non-consonant ("umpoled") pattern by a platinum-catalyzed transannular hydroalkoxylation of a cycloalkyne precursor. This key intermediate was assembled from three building blocks (29, 41 and 47 (or 65)) by Yamaguchi esterification, Stille cross-coupling and a macrocyclization by ring-closing alkyne metathesis (RCAM). This approach illustrates the exquisite alkynophilicity of the catalysts chosen for the RCAM and alkyne hydroalkoxylation steps, which activate triple bonds with remarkable ease but left up to five other p-systems in the respective substrates intact. Interestingly, the inverse chemoselectivity pattern was exploited for the preparation of the tetrahydrofuran building blocks 47 and 65 carrying the different side chains of the two target macrolides. These fragments derive from a common aldehyde precursor 46 formed by an exquisitely alkene-selective cobalt-catalyzed oxidative cyclization of the diunsaturated alcohol 44, which left an adjacent acetylene group untouched. The northern sector 29 was prepared by a two-directional Marshall propargylation strategy, whereas the highly adorned acid subunit 41 derives from d-glutamic acid by an intramolecular oxa-Michael addition and a proline-mediated hydroxyacetone aldol reaction as the key steps; the necessary Me3Sn-group on the terminus of 41 for use in the Stille coupling was installed via enol triflate 39, which was obtained by selective deprotonation/triflation of the ketone site of the precursor 38 without competing enolization of the ester also present in this particular substrate.

First synthesis of polyoxin M

Chiral enolate derived from (4R)-4-tert-butyldiphenylsilyloxymethyl-4-butanolide 10 with lithium hexamethyldisilyazide (LiHMDS) was treated with trisyl azide, followed by addition of TMSCl to give (2S,4R)-2-azido-4-[(tert-butyldiphenylsilyloxy)methyl]-4-b

Syntheses of 2′,3′-dideoxy-L-glyceropentofuranosyl C-nucleosides

2′,3′-Dideoxy-L-C-nucleosides, 4-amino-8-(2,3-dideoxy-L-glyceropentofuranosyl)pyrazolo[1,5-a]-1,3,5-triazines (9 and 10), 4-amino-7-(2,3-dideoxy-L-glyceropentofuranosyl)-3H,5H-pyrrolo[3,2-d]pyrimidines (17 and 18), 7-(2,3-dideoxy-L-glyceropentofuranosyl)-