58857-02-6

Basic information

• Product Name: Ambruticin
• Synonyms: Ambruticin
• CAS NO: 58857-02-6
• Molecular Formula: C₂₈H₄₂O₆
• Molecular Weight: 474.634
• Mol File: 58857-02-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 611.5°C at 760 mmHg
• Flash Point: 194.8°C
• Appearance: /
• Density: 1.201g/cm³
• Vapor Pressure: 1.66E-17mmHg at 25°C
• Refractive Index: 1.617
• CAS DataBase Reference: Ambruticin(CAS DataBase Reference)
• NIST Chemistry Reference: Ambruticin(58857-02-6)
• EPA Substance Registry System: Ambruticin(58857-02-6)

Safety Data

• Hazardous Substances Data: 58857-02-6(Hazardous Substances Data)

Usage

Originator

Ambruticin,Universitet Karlsruhe (TH)

Uses

Antifungal.

Therapeutic Function

Antifungal

InChI:InChI=1/C28H42O6/c1-6-24-17(3)8-11-25(34-24)18(4)13-16(2)7-9-21-19(5)22(21)10-12-26-28(32)23(29)14-20(33-26)15-27(30)31/h7-10,12-13,16,19-26,28-29,32H,6,11,14-15H2,1-5H3,(H,30,31)/b9-7+,12-10+,18-13+/t16-,19-,20+,21+,22+,23+,24-,25-,26+,28-/m1/s1

Upstream product

• 130799-18-7 5β,6α-dibenzyloxypolyangioic acid 
• 130799-17-6 methyl 5β,6α-dibenzyloxypolyangioate 
• 62711-77-7 methyl 5β,6α-dihydroxypolyangioate 
• 63511-77-3 (2S,3R,4S,6R)-2-((E)-2-((1S,2S,3R)-2-((R,1E,4E)-5-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methylhexa-1,4-dien-1-yl)-3-methylcyclopropyl)vinyl)-6-(2-hydroxyethyl)tetrahydro-2H-pyran-3,4-diol 
• 125637-07-2 (R)-3-hydroxy-2-methylpent-1-ene 
• 393530-33-1 [4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl] methanol 
• 208344-94-9 (1R,5S,6R)-(-)-6-methyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 393530-39-7 Diazo-acetic acid (Z)-but-2-enyl ester 
• 353490-93-4 ((2S,3S)-3-allyloxiran-2-yl)methanol 
• 393530-64-8 [2R,6R,2(2'S,3'E)]-2-(1-hydroxy-2-methyl-3-penten-4-yl)-5-methyl-6-ethyl-3,6-dihydropyran 
• 393530-60-4 1-[(2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-2-pyranyl]-1-ethanone 
• 393530-46-6 (1S,2S,3S)-1-hydrocymethyl-3-methyl-2-(tert-butyldimethylsilyloxy)methylcyclopropane 
• 393530-62-6 [2R,6R,2(2'R)]-2-[2'-hydroxy-3'-penten-2'(Z)-yl]-5-methyl-6-ethyl-3,6-dihydropyran 
• 616895-58-0 (1R,2S,3R)-2-hydroxymethyl-3-methyl-1-(morpholino)carbonylcyclopropane 

Downstream Products

• 62711-77-7 methyl 5β,6α-dihydroxypolyangioate 
• 75880-65-8 (1S,2S)-3-methylcyclopropane-1,2-dicarboxylic acid 
• 498580-05-5 methyl [(2S,4S,5R,6S)-4,5-bis(tert-butyldimethylsilyloxy)-6-hydroxymethyltetrahydro-2H-pyran-2-yl] acetate 
• 393530-66-0 methyl 5β,6α-di-tert-butyldimethylsilyloxypolyangioate 

Relevant articles and documents

Total synthesis of (+)-ambruticin S: Probing the pharmacophoric subunit

An enantioselective synthesis of the antifungal natural product (+)-ambruticin S has been accomplished starting with the readily available methyl α-d-glucopyranoside, (R)-Roche ester, and (S)-glycidol as chirons, which encompassed seven of the 10 stereogenic centers of the target molecule. The remaining three centers were set by a highly diastereoselective, asymmetric cyclopropanation employing a chiral, nonracemic phosphonamide reagent. Our strategy for the construction of the dihydropyran subunit involved a highly syn-selective Lewis acid catalyzed 6-endo-trig cyclization. Other key steps in the synthesis featured an epoxide opening with a dithiane anion, two efficient phosphonamide-anion based olefinations, and a late-stage C-glycosylation.

Total synthesis of ambruticin.

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Total synthesis of (+)-ambruticin [18]

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