(-)-Virginiamycin M2

Base Information

• Chemical Name: (-)-Virginiamycin M2
• CAS No.: 21102-49-8
• Molecular Formula: C₂₈H₃₇N₃O₇
• Molecular Weight: 527.618
• European Community (EC) Number: 606-706-0
• Wikipedia: Pristinamycin_IIB

Synonyms:(-)-virginiamycin M2;virginiamycin M2

Chemical Property of (-)-Virginiamycin M2

Chemical Property:

• Vapor Pressure: 1.11E-27mmHg at 25°C
• Boiling Point: 809.5°Cat760mmHg
• PKA: 13.18±0.70(Predicted)
• Flash Point: 443.3°C
• PSA: 142.53000
• Density: 1.25g/cm³
• LogP: 2.60550
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 527.26315053
• Heavy Atom Count: 38
• Complexity: 974

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC(=O)NCC=CC(=CC(CC(=O)CC2=NC(=CO2)C(=O)N3CCCC3C(=O)OC1C(C)C)O)C
• Isomeric SMILES: CC1/C=C\C(=O)NC/C=C\C(=C/C(CC(=O)CC2=NC(=CO2)C(=O)N3CCCC3C(=O)OC1C(C)C)O)\C
• General Description: (-)-Virginiamycin M2 is a complex macrocyclic antibiotic belonging to the group A virginiamycins, known for its potent activity against resistant bacterial strains. It features a 23-membered macrocyclic structure with multiple stereocenters and a trisubstituted (E,E)-diene, synthesized through a convergent strategy involving enantioselective Rh(II)- or Cu(I)-catalyzed carbenoid Si–H insertion, cross-coupling, and SmI2-mediated macrocyclization. (-)-Virginiamycin M2, also referred to as Pristinamycin IIB or Ostreogrycin G, exhibits significant biological potential, and its synthetic route enables the exploration of analogues for further antibiotic development.

Technology Process of (-)-Virginiamycin M2

There total 47 articles about (-)-Virginiamycin M2 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: 90.0%

C37H59N3O7Si2 → virginiamycin M2 (21102-49-8)

Guidance literature:

With tetrabutyl ammonium fluoride; Imidazole hydrochloride;

DOI:10.1038/s41586-020-2761-3

Reference yield: 78.0%

(12E,17E,19E)-(7R,10R,11R,21S)-21-(tert-Butyl-diphenyl-silanyloxy)-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triaza-tricyclo[23.2.1.03,7]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14,23-tetraone (175551-76-5) → virginiamycin M2 (21102-49-8)

Guidance literature:

With pyridine hydrogenfluoride; In dichloromethane; Ambient temperature;

DOI:10.1021/ja954311z

Reference yield:

(12E,17E,19E)-(7R,10R,11R,21S)-21-(tert-Butyl-diphenyl-silanyloxy)-23-hydroxy-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triaza-tricyclo[23.2.1.03,7]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14-trione → virginiamycin M2 (21102-49-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

2: 78 percent / HF*pyridine / CH₂Cl₂ / Ambient temperature

With Dess-Martin periodane; pyridine hydrogenfluoride; In dichloromethane;

DOI:10.1021/ja954311z

upstream raw materials:

(12E,17E,19E)-(7R,10R,11R,21S)-21-(tert-Butyl-diphenyl-silanyloxy)-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triaza-tricyclo[23.2.1.0^3,7]octacosa-1⁽²⁷⁾,12,17,19,25⁽²⁸⁾-pentaene-2,8,14,23-tetraone

t-butyl 2-(bromomethyl)oxazole-4-carboxylate

(E)-(4R,5R)-5-Hydroxy-4,6-dimethyl-hept-2-enal

(E)-3-[(S)-2-(1-Ethyl-1-methoxy-propyl)-pyrrolidin-1-yl]-pent-2-enoic acid methyl ester

Refernces

Total synthesis of (-)-virginiamycin m₂: Application of crotylsilanes accessed by enantioselective Rh(II) or Cu(I) promoted carbenoid Si-H insertion

10.1021/jo202119p

The research focuses on the stereoselective synthesis of the antibiotic (?)-virginiamycin M2. The study aims to develop an efficient and enantioselective synthesis of this complex antibiotic, which is part of the group A virginiamycins known for their potent antibiotic activity against various resistant bacterial strains. The researchers employed a convergent strategy involving a series of key steps, including the use of chiral silane reagents prepared through Rh(II)- or Cu(I)-catalyzed carbenoid Si?H insertion to introduce the desired olefin geometry and stereocenters. They also utilized a modified Negishi cross-coupling or titanium-mediated alkyne?alkyne reductive coupling to assemble the trisubstituted (E,E)-diene and employed a SmI2-mediated macrocyclization to construct the 23-membered macrocycle scaffold. The synthesis was completed with a final deprotection step to reveal (?)-virginiamycin M2. The study concludes that the developed synthetic route is highly convergent, achieving the total synthesis in 19 steps with a longest linear sequence of 10 steps, and offers a modular approach that could facilitate the design and synthesis of analogues for further exploration of the biological potential of group A virginiamycins.

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