(2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,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}-5-oxopent-3-en-2-yl acetate

Base Information

• Chemical Name: (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,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}-5-oxopent-3-en-2-yl acetate
• CAS No.: 146478-72-0
• Molecular Formula: C27H41 N O8
• Molecular Weight: 507.624
• DSSTox Substance ID: DTXSID801098397
• Nikkaji Number: J1.445.099H
• Wikidata: Q27134411
• Metabolomics Workbench ID: 64249
• ChEMBL ID: CHEMBL494107

Synonyms:FR 901464;FR-901464;FR901464

Chemical Property of (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,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}-5-oxopent-3-en-2-yl acetate

Chemical Property:

• Vapor Pressure: 7.94E-23mmHg at 25°C
• Boiling Point: 702.7°Cat760mmHg
• Flash Point: 378.8°C
• Density: 1.21g/cm³
• XLogP3: 2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 507.28321727
• Heavy Atom Count: 36
• Complexity: 900

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C(OC1CC=C(C)C=CC2C(C3(CC(O2)(C)O)CO3)O)C)NC(=O)C=CC(C)OC(=O)C
• Isomeric SMILES: C[C@H]1C[C@H]([C@H](O[C@H]1C/C=C(\C)/C=C/[C@@H]2[C@H]([C@@]3(C[C@@](O2)(C)O)CO3)O)C)NC(=O)/C=C\[C@H](C)OC(=O)C
• General Description: **Conclusion:** 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, also known as FR901464, is a potent anticancer natural product with significant antitumor and antiproliferative activities. Its synthetic analogue, meayamycin, demonstrates even greater potency, achieving a GI50 value of 10 pM in MCF-7 breast cancer cells. 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's complex structure, featuring multiple stereocenters and functional groups, was constructed using advanced synthetic strategies, including diene-ene cross olefin metathesis and asymmetric alkynylation. Studies on its decomposition pathways have informed the design of more stable analogues, enhancing its potential as a therapeutic agent.

Technology Process of (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,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}-5-oxopent-3-en-2-yl acetate

There total 79 articles about (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,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}-5-oxopent-3-en-2-yl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

spliceostatin A (391611-36-2) → FR 901464 (146478-72-0)

Guidance literature:

With pyridinium p-toluenesulfonate; In tetrahydrofuran; water; at 0 ℃; for 72h; Inert atmosphere;

DOI:10.1021/ol4024634

Reference yield: 75.0%

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 (310398-04-0) → FR 901464 (146478-72-0)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water;

DOI:10.1021/ja0055357

Reference yield: 32.0%

(3R,4R,5R,7S)-7-Methyl-5-vinyl-1,6-dioxa-spiro[2.5]octane-4,7-diol (882028-32-2) + (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 (882028-31-1) → FR 901464 (146478-72-0)

Guidance literature:

In 1,2-dichloro-ethane; at 23 ℃; for 10 - 11h; Product distribution / selectivity;

upstream raw materials:

spliceostatin A

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

(3R,4R,5R,7S)-7-Methyl-5-vinyl-1,6-dioxa-spiro[2.5]octane-4,7-diol

(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

Downstream raw materials:

spliceostatin A

Refernces

Total syntheses, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue

10.1021/ja067870m

The study presents a total synthesis of the potent anticancer natural product FR901464 and its low picomolar analogue meayamycin. The researchers employed a convergent and enantioselective synthetic approach, utilizing key reactions such as diene-ene cross olefin metathesis, Zr/Ag-promoted alkynylation, Red-Al reduction, Mislow-Evans-type [2,3]-sigmatropic rearrangement, and Carreira asymmetric alkynylation. These reactions were essential for setting the stereocenters and constructing the complex molecular framework of FR901464. The study also investigated the decomposition pathways of FR901464 under physiological conditions, leading to the rational design of a more stable right fragment analogue, which was then used to synthesize meayamycin. The synthesized compounds were tested for their antitumor and antiproliferative activities, with meayamycin showing exceptional potency with a GI50 value of 10 pM in MCF-7 breast cancer cells. The chemicals used in the study served as synthetic building blocks, reagents for key reactions, and analytical tools to characterize the synthesized compounds and assess their biological activities.

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