Hyrtiosal

Base Information

• Chemical Name: Hyrtiosal
• CAS No.: 138355-07-4
• UNII: WX5FRH0E65
• ChEMBL ID: CHEMBL1078661
• Metabolomics Workbench ID: 172420,178055
• Wikidata: Q104401092
• Mol file: 138355-07-4.mol

Synonyms:hyrtiosal

Chemical Property of Hyrtiosal

Chemical Property:

• XLogP3: 6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 386.28209507
• Heavy Atom Count: 28
• Complexity: 615

Purity/Quality:

80%，90%，95%，98%，99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC3(C2CC(C3CC(C4=COC=C4)O)(C)C=O)C)C)C
• Isomeric SMILES: C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2C[C@]([C@H]3C[C@@H](C4=COC=C4)O)(C)C=O)C)(C)C

Technology Process of Hyrtiosal

There total 12 articles about Hyrtiosal 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: 99.0%

13S,16S-19,25-epoxy-17(25),18-dien-16-acetoxyhyrtiosan-12-al (138355-08-5) → hyrtiosal (138355-07-4)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 2h;

DOI:10.1055/s-2002-33332

Reference yield: 67.0%

16R,13S-12-Ethylenedithio-19,25-epoxy-17(25),18-diene-16-hyrtiosanol (325788-16-7) → hyrtiosal (138355-07-4) + 13S,16R-19,25-epoxy-17(25),18-diene-16-hydroxyhyrtiosan-12-al

Guidance literature:

With mercury(II) perchlorate; calcium carbonate; In tetrahydrofuran; at 20 ℃; for 0.166667h;

DOI:10.1055/s-2002-33332

Reference yield: 57.0%

16S,13S-12-Ethylenedithio-19,25-epoxy-17(25),18-diene-16-hyrtiosanol (325788-18-9) → hyrtiosal (138355-07-4) + 13S,16R-19,25-epoxy-17(25),18-diene-16-hydroxyhyrtiosan-12-al

Guidance literature:

With mercury(II) perchlorate; calcium carbonate; In tetrahydrofuran; at 20 ℃; for 0.166667h;

DOI:10.1055/s-2002-33332

upstream raw materials:

16S,13S-12-Ethylenedithio-19,25-epoxy-17⁽²⁵⁾,18-diene-16-hyrtiosanol

16R,13S-12-Ethylenedithio-19,25-epoxy-17⁽²⁵⁾,18-diene-16-hyrtiosanol

13S,16S-19,25-epoxy-17⁽²⁵⁾,18-dien-16-acetoxyhyrtiosan-12-al

15a-homo-13S-11(12->13)-abeo-12-ethylenedithia-15-isoanticopalal

Refernces

Hyrtiosanes from labdanes: (-)-Hyrtiosal from sclareol

10.1055/s-2002-33332

The study details the synthesis of (–)-hyrtiosal and its C-16 epimer from sclareol. The researchers utilized a series of chemical transformations to convert sclareol into hyrtiosal, a sesterterpenoid with a unique tricarbocyclic skeleton. Key steps included the formation of an epoxide from methyl isoanticopalate derived from sclareol, rearrangement to an aldehyde using BF3?Et2O, protection and homologation of the aldehyde, and coupling with 3-lithiofuran to introduce a furan ring. The absolute configuration of hyrtiosal was determined through X-ray analysis of its derivative. The synthesized compounds were tested for antitumor activity against various human tumor cell lines, showing promising results with IC50 values ranging from 2.4 to 16.2 μM. The study provides a novel route for transforming labdane skeletons into hyrtiosane skeletons, contributing to the field of natural product synthesis and potentially offering new avenues for the development of antitumor agents.