71980-98-8

Basic information

• Product Name: 9-[[(2E)-4-[[(2S,3R,4R,5S)-3α,4α-Dihydroxy-5β-[(2E,4S,5S)-5-hydroxy-4-methyl-2-hexenyl]tetrahydro-2H-pyran]-2β-yl]-3-methyl-2-butenoyl]oxy]nonanoic acid
• Synonyms: 9-[[(2E)-4-[[(2S,3R,4R,5S)-3α,4α-Dihydroxy-5β-[(2E,4S,5S)-5-hydroxy-4-methyl-2-hexenyl]tetrahydro-2H-pyran]-2β-yl]-3-methyl-2-butenoyl]oxy]nonanoic acid;Pseudomonic acid C
• CAS NO: 71980-98-8
• Molecular Formula: C26H44O8
• Molecular Weight: 484.62276
• Mol File: 71980-98-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 656.2°Cat760mmHg
• Flash Point: 210.3°C
• Appearance: /
• Density: 1.125g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.516
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), methanol (Slightly)
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: 9-[[(2E)-4-[[(2S,3R,4R,5S)-3α,4α-Dihydroxy-5β-[(2E,4S,5S)-5-hydroxy-4-methyl-2-hexenyl]tetrahydro-2H-pyran]-2β-yl]-3-methyl-2-butenoyl]oxy]nonanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 9-[[(2E)-4-[[(2S,3R,4R,5S)-3α,4α-Dihydroxy-5β-[(2E,4S,5S)-5-hydroxy-4-methyl-2-hexenyl]tetrahydro-2H-pyran]-2β-yl]-3-methyl-2-butenoyl]oxy]nonanoic acid(71980-98-8)
• EPA Substance Registry System: 9-[[(2E)-4-[[(2S,3R,4R,5S)-3α,4α-Dihydroxy-5β-[(2E,4S,5S)-5-hydroxy-4-methyl-2-hexenyl]tetrahydro-2H-pyran]-2β-yl]-3-methyl-2-butenoyl]oxy]nonanoic acid(71980-98-8)

Safety Data

• Hazardous Substances Data: 71980-98-8(Hazardous Substances Data)

Usage

Uses

Pseudomonic Acid C, is the analogue of Pseudomonic Acid D (P839520) which is an antibiotic isolated from Pseudomonas fluorescens.

InChI:InChI=1/C26H44O8/c1-18(16-24(30)33-14-9-7-5-4-6-8-13-23(28)29)15-22-26(32)25(31)21(17-34-22)12-10-11-19(2)20(3)27/h10-11,16,19-22,25-27,31-32H,4-9,12-15,17H2,1-3H3,(H,28,29)/b11-10+,18-16+/t19-,20+,21+,22+,25-,26+/m1/s1

Upstream product

• 78088-28-5 ethyl (2S,3S)-3-hydroxy-2-methylbutanoate 
• 528869-25-2 (3S,4R,5R)-2-Bromo-tetrahydro-pyran-3,4,5-triol 
• 89726-71-6 (4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol 
• 89726-70-5 (3aR,7S,7aR)-7-(2-Benzenesulfonyl-ethyl)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 89726-69-2 2-((3aR,7S,7aR)-4-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-ethanol 
• 83160-44-5 (3aR,7S,7aR)-7-Allyl-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 87-72-9 L-arabinofuranose 
• 115118-87-1 <3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol<<(1,1-dimethylethyl)dimethylsilyl>oxy>acetate 
• 107148-29-8 <3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one 
• 107148-30-1 (S)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-yn-2-ol 
• 107148-26-5 <3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol 
• 107148-25-4 <3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde 
• 107148-23-2 (5S-cis)-5,6-dihydro-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-ol 
• 115118-79-1 *,R^*)>-5,6-dihydro-N-(1-phenylethyl)-2H-pyran-2-acetamide 

Relevant articles and documents

Selected Mutations Reveal New Intermediates in the Biosynthesis of Mupirocin and the Thiomarinol Antibiotics

Thiomarinol and mupirocin are assembled on similar polyketide/fatty acid backbones and exhibit potent antibiotic activity against methicillin-resistant Staphylococcus aureus (MRSA). They both contain a tetrasubstituted tetrahydropyran (THP) ring that is essential for biological activity. Mupirocin is a mixture of pseudomonic acids (PAs). Isolation of the novel compound mupirocin P, which contains a 7-hydroxy-6-keto-substituted THP, from a ΔmupP strain and chemical complementation experiments confirm that the first step in the conversion of PA-B into the major product PA-A is oxidation at the C6 position. In addition, nine novel thiomarinol (TM) derivatives with different oxidation patterns decorating the central THP core were isolated after gene deletion (tmlF). These metabolites are in accord with the THP ring formation and elaboration in thiomarinol following a similar order to that found in mupirocin biosynthesis, despite the lack of some of the equivalent genes. Novel mupirocin–thiomarinol hybrids were also synthesized by mutasynthesis.

Total Synthesis of Pseudomonic Acid C

Two approaches to the synthesis of aldehyde 28, a key intermediate in the total synthesis of pseudomonic acid C, were developed.One asymmetric route from the chiral hydroxy ester 11 proceeded in 13 steps via the hydroxy lactone 17.A shorter approach involved the Lewis acid catalyzed cycloaddition of formaldehyde to the chiral diene 23a to give 22a, which was separated from its diastereomer and then converted into 28 in seven steps.The introduction of the C-8 side chain was initially accomplished by Julia coupling of 28 with the sulfone anion derived from 40 to give the olefin 34.The stereoselective preparation of 34 was also carried out, via the ester 46a, by a novel ester enolate Claisen rearrangement of the silyl-protected glycolate ester 44.A third approach directed toward the synthesis of the side chain entailed controlling the C-10 stereochemistry of the benzyl-protected glycolate ester 48 by reduction of a precursor propargyl ketone 27 with Alpine borane.Ester enolate Claisen rearrangement then gave the ester 46b with excellent stereocontrol.

Total synthesis of (+)-pseudomonic acid C

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