146478-72-0

Basic information

• Product Name: 4(S)-Acetoxy-N-[(2R,3R,5S,6S)-6-[5-[(3R,4R,5R,7S)-4,7-dihydroxy-7-methyl-1,6-dioxaspiro[2.5]octan-5-yl]-3-methyl-2(E),4(E)-pentadienyl]-2,5-dimethyltetrahydropyran-3-yl]-2(Z)-pentenamide
• Synonyms: WB-2663B; FR-901464; (1S,2E)-4-{[(2R,5S,6S)-6-{(2E,4E)-5-[(4R,5R,7S)-4,7-dihydroxy-7-methyl-1,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-1-methyl-4-oxobut-2-en-1-yl acetate
• CAS NO: 146478-72-0
• Molecular Formula: C₂₇H₄₁NO₈
• Molecular Weight: 507.6163
• Mol File: 146478-72-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 702.7°C at 760 mmHg
• Flash Point: 378.8°C
• Density: 1.21g/cm³
• Vapor Pressure: 7.94E-23mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: 4(S)-Acetoxy-N-[(2R,3R,5S,6S)-6-[5-[(3R,4R,5R,7S)-4,7-dihydroxy-7-methyl-1,6-dioxaspiro[2.5]octan-5-yl]-3-methyl-2(E),4(E)-pentadienyl]-2,5-dimethyltetrahydropyran-3-yl]-2(Z)-pentenamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4(S)-Acetoxy-N-[(2R,3R,5S,6S)-6-[5-[(3R,4R,5R,7S)-4,7-dihydroxy-7-methyl-1,6-dioxaspiro[2.5]octan-5-yl]-3-methyl-2(E),4(E)-pentadienyl]-2,5-dimethyltetrahydropyran-3-yl]-2(Z)-pentenamide(146478-72-0)
• EPA Substance Registry System: 4(S)-Acetoxy-N-[(2R,3R,5S,6S)-6-[5-[(3R,4R,5R,7S)-4,7-dihydroxy-7-methyl-1,6-dioxaspiro[2.5]octan-5-yl]-3-methyl-2(E),4(E)-pentadienyl]-2,5-dimethyltetrahydropyran-3-yl]-2(Z)-pentenamide(146478-72-0)

Safety Data

• Hazardous Substances Data: 146478-72-0(Hazardous Substances Data)

Usage

General Description

The chemical "4(S)-Acetoxy-N-[(2R,3R,5S,6S)-6-[5-[(3R,4R,5R,7S)-4,7-dihydroxy-7-methyl-1,6-dioxaspiro[2.5]octan-5-yl]-3-methyl-2(E),4(E)-pentadienyl]-2,5-dimethyltetrahydropyran-3-yl]-2(Z)-pentenamide" is a complex molecule containing a variety of functional groups and structural features. It is acetylated and contains cyclohexane rings, pentadienyl chains, and a tetrahydropyran ring. It also includes hydroxyl and methyl groups. The molecule has asymmetric carbon centers and double bonds, contributing to its stereochemical complexity. It exhibits a mixture of acetoxy, amide, and alkene functional groups, and its complex structure suggests potential biological activity or synthetic utility.

Upstream product

• 391611-36-2 spliceostatin A 
• 310398-04-0 Acetic acid (Z)-(S)-3-{(2R,3R,5S,6S)-6-[(2E,4E)-5-((3R,4R,5R)-4-hydroxy-7-methylene-1,6-dioxa-spiro[2.5]oct-5-yl)-3-methyl-penta-2,4-dienyl]-2,5-dimethyl-tetrahydro-pyran-3-ylcarbamoyl}-1-methyl-allyl ester 
• 882028-32-2 (3R,4R,5R,7S)-7-Methyl-5-vinyl-1,6-dioxa-spiro[2.5]octane-4,7-diol 
• 882028-31-1 (S,Z)-5-(((2R,3R,5S,6S)-2,5-dimethyl-6-((E)-3-methylpenta-2,4-dien-1-yl)tetrahydro-2H-pyran-3-yl)amino)-5-oxopent-3-en-2-yl acetate 
• 882028-36-6 (S)-4-formylbut-3-yn-2-yl acetate 
• 882028-38-8 tert-butyl (3R,4R)-4-hydroxypent-1-en-3-ylcarbamate 
• 1020209-78-2 (2R,3R,5S,6S)-6-allyl-2,5-dimethyltetrahydro-2H-pyran-3-amine 
• 882028-35-5 (E)-(2S)-6-phenylhex-5-en-3-yn-2-yl acetate 
• 882028-37-7 tert-butyl (4R,5R)-2,2,5-trimethyl-4-vinyl-oxazolidine-3-carboxylate 
• 882028-40-2 tert-butyl ((2R,3R)-2,5-dimethyl-3,6-dihydro-2H-pyran-3-yl)carbamate 
• 882028-41-3 tert-butyl ((2R,3R)-2,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-3-yl)carbamate 
• 882028-47-9 (E)-(R)-4-Hydroxy-4-[(R)-2-(2-methyl-allyl)-oxiranyl]-but-2-enoic acid methyl ester 
• 882028-43-5 tert-butyl [(2R,3R,5S,6S)-2,5-dimethyl-6-(prop-2-en-1-yl)tetrahydro-2H-pyran-3-yl]carbamate 
• 882028-50-4 (1R,2R)-1-[(R)-2-(2-Methyl-allyl)-oxiranyl]-1-triethylsilanyloxy-but-3-en-2-ol 

Downstream Products

• 391611-36-2 spliceostatin A 

Relevant articles and documents

Enantioselective syntheses of FR901464 and spliceostatin A: Potent inhibitors of spliceosome

Enantioselective syntheses of FR901464 and spliceostatin A, potent spliceosome inhibitors, are described. The synthesis of FR901464 has been accomplished in a convergent manner in 10 linear steps (20 total steps). The A-tetrahydropyran ring was constructed from (R)-isopropylidene glyceraldehyde. The functionalized tetrahydropyran B-ring was synthesized utilizing a Corey-Bakshi-Shibata reduction, an Achmatowicz reaction, and a stereoselective Michael addition as the key steps. Coupling of A- and B-ring fragments was accomplished via cross-metathesis.

FR901464 AND ANALOGS WITH ANTITUMOR ACTIVITY AND METHOD FOR THEIR PREPARATION

The present invention provides analogs of FR901464, as well as a methodology for preparing FR901464 and its analogs. These compounds display an anti-cancer activity and are candidates for therapies against a number of disease states associated with dysfunctional RNA splicing.

Total synthesis of FR901464: Second generation

FR901464, a potent cell cycle inhibitor, was synthesized in a convergent manner using natural chiral pool, l-threonine, ethyl (S)-lactate and 2-deoxy-d-glucose as starting materials.