Decarestrictine D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01695 |
| CAS | 127393-89-9 |
| Molecular Weight | 216.23 |
| Molecular Formula | C10H16O5 |
| Purity | >98% |
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Description
Decarestrictin D is a cholesterol biosynthesis inhibitor with a Decanolide structure produced by Penicillum sunplicissimum and Pen. corylophilufn.
Specification
| Synonyms | (4S,5S,8S,10R,E)-4,5,8-Trihydroxy-10-methyl-3,4,5,8,9,10-hexahydro-2H-oxecin-2-one |
| Storage | -20°C |
| IUPAC Name | (2R,4S,7S,8S)-4,7,8-trihydroxy-2-methyl-2,3,4,7,8,9-hexahydrooxecin-10-one |
| Canonical SMILES | CC1CC(C=CC(C(CC(=O)O1)O)O)O |
| InChI | InChI=1S/C10H16O5/c1-6-4-7(11)2-3-8(12)9(13)5-10(14)15-6/h2-3,6-9,11-13H,4-5H2,1H3/t6-,7-,8+,9+/m1/s1 |
| InChI Key | HWMMWMJBUOCCFZ-HXFLIBJXSA-N |
Properties
| Appearance | White Crystal |
| Solubility | Soluble in DMSO |
Reference Reading
1. Botryolides A-E, decarestrictine analogues from a fungicolous Botryotrichum sp. (NRRL 38180)
Arlene A Sy, Dale C Swenson, James B Gloer, Donald T Wicklow J Nat Prod. 2008 Mar;71(3):415-9. doi: 10.1021/np070610d. Epub 2007 Dec 30.
Four new decarestrictine analogues (botryolides A-D; 1- 4), a biosynthetically related gamma-lactone (botryolide E; 5), and the known compounds decarestrictine D ( 6) and sterigmatocystin have been isolated from cultures of a fungicolous isolate of Botryotrichum sp. (NRRL 38180). The structures of these compounds were determined by analysis of 2D NMR and ESIMS data. The relative configurations of 1- 5 were established on the basis of NMR data and/or X-ray diffraction analysis, while the absolute configuration of 1 was assigned using the modified Mosher method.
2. Stereoselective synthesis of decarestrictine D from a previously inaccessible (2Z,4E)-alkadienyl alcohol precursor
Yuichi Kobayashi, Moriteru Asano, Shinya Yoshida, Akira Takeuchi Org Lett. 2005 Apr 14;7(8):1533-6. doi: 10.1021/ol050148t.
[reaction: see text] The core structure of decarestrictine D was constructed by stereoselective oxygenation of (2Z,4E)-alkadienyl alcohol, which could be synthesized by a nickel-catalyzed coupling reaction between the corresponding cis bromide and trans borate. Efficiency in macrocyclization of the seco acid with Yamaguchi reagent was found to be protective-group-dependent, and the best yield of 40% was obtained with the seco acid with tri-MOM protective groups.
3. Nickel-catalyzed coupling producing (2Z)-2,4-alkadien-1-ols, conversion to (E)-3-alkene-1,2,5-triol derivatives, and synthesis of decarestrictine D
Yuichi Kobayashi, Shinya Yoshida, Moriteru Asano, Akira Takeuchi, Hukum P Acharya J Org Chem. 2007 Mar 2;72(5):1707-16. doi: 10.1021/jo0623890. Epub 2007 Jan 25.
The 3-alkene-1,2,5-triol structure is not only a major framework of biologically important molecules but also a new functional-group-rich unit for synthesis of polyols and sugars. A method furnishing such triol derivatives 8 was developed and successfully applied to synthesis of decarestrictine D (18). First, coupling reaction of the unprotected alcohols 2 with borates 4 was investigated to produce the dienyl alcohols 6 with NiCl2(dppf) in Et2O/THF (5:1) at room temperature. The hydroxyl-group-directed epoxidation of 6 followed by palladium-catalyzed reaction with AcOH (Scheme 1) furnished 3-alkene-1,2,5-triol derivatives 8. Since each step proceeded with high stereo- and regioselectivities, the stereochemistry of 8 has been correlated with the olefin geometry of 6. With the above transformation in mind, synthesis of the full carbon skeleton of decarestrictine D (18) could be designed easily and was completed successfully. Furthermore, a new seco acid 19b with the MOM protective group for the three hydroxyl groups was found to afford macrolide 48 in a yield higher than those reported previously.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
