Repromicin

Base Information

• Chemical Name: Repromicin
• CAS No.: 56689-42-0
• Molecular Formula: C31H51 N O8
• Molecular Weight: 565.748
• UNII: G5WU4SAO6B
• DSSTox Substance ID: DTXSID501024032
• Wikidata: Q27278808
• NCI Thesaurus Code: C152193
• ChEMBL ID: CHEMBL3138624
• Mol file: 56689-42-0.mol

Synonyms:antibiotic M-4365 G2;de-epoxy rosamicin;de-epoxy rosamicin phosphate;de-epoxy rosamicin sulfate;de-epoxy rosamicin tartrate, (R-(R*,R*))-isomer;de-epoxy rosamicin, (12Z)-isomer;de-epoxy rosamicin, dodecysulfate-(12E)-isomer;de-epoxy rosamicin, octadecanoate-(12E)-isomer;de-epoxy rosamicin, potassium dihydrogen phosphate;M-4365G2

Chemical Property of Repromicin

Chemical Property:

• Vapor Pressure: 2.44E-24mmHg at 25°C
• Boiling Point: 726°C at 760 mmHg
• Flash Point: 392.9°C
• PSA: 122.60000
• Density: 1.13g/cm³
• LogP: 3.45920
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 565.36146759
• Heavy Atom Count: 40
• Complexity: 902

Purity/Quality:

REPROMICIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(CC(O2)C)N(C)C)O)CC=O)C)C)C
• Isomeric SMILES: CC[C@@H]1[C@H](/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H](C[C@H](O2)C)N(C)C)O)CC=O)C)\C)C
• Uses: Antibacterial.

Technology Process of Repromicin

There total 32 articles about Repromicin 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: 61.0%

rosaramicin (35834-26-5) → 12,13-de-epoxy-12,13-didehydrorosaramicin (56689-42-0)

Guidance literature:

With hydrogenchloride; titanium(III) chloride; In methanol; water; at 0 ℃; for 3h; pH 1.3;

DOI:10.1039/P19890000787

Reference yield: 57.1%

12,13-de-epoxy-12,13-dehydro-20-dihydrorosaramicin (58947-83-4) → 12,13-de-epoxy-12,13-didehydrorosaramicin (56689-42-0)

Guidance literature:

With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) triflate; In acetonitrile; at 20 ℃; for 1.5h;

DOI:10.1021/jacs.7b02875

Reference yield:

rosaramicin (35834-26-5) → 12,13-de-epoxy-12,13-didehydrorosamicin 20-dimethyl acetal (61486-91-7) + 12,13-de-epoxy-12,13-didehydrorosaramicin (56689-42-0)

Guidance literature:

With hydrogenchloride; titanium(III) chloride; In methanol; water; at 0 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; pH 1.0;

DOI:10.1039/P19890000787

upstream raw materials:

rosaramicin

rosaramicin N-oxide

12,13-de-epoxy-12,13-didehydrorosamicin 20-dimethyl acetal

rosaramicin 20-dimethyl acetal 3'-N-oxide

Downstream raw materials:

rosaramicin

5-O-desosaminyltylonolide

(9R)-12,13-de-epoxy-12,13-dehydro-20-deoxo-9-dehydro-rosaramicin 20-diphenylthioacetal

(9S)-12,13-de-epoxy-12,13-dehydro-20-deoxo-9-dehydro-rosaramicin 20-diphenylthioacetal

Refernces

• 1、 Fishman, Andrew G.,Mallams, Alan K.,Rossman, Randall R.. "Semisynthetic Macrolide Antibacterials Derived from Tylosin. Synthesis of 3-O-Acetyl-23-O-demycinosyl-4''-O-isovaleryltylosin and Related Compounds, as well as the 12,13-Epoxy Derivatives". . p. 787 - 798. Retrieved 2007/10/02.