CID 20407245

Base Information

• Chemical Name: CID 20407245
• CAS No.: 3922-90-5
• Molecular Formula: C₃₅H₆₁NO₁₂
• Molecular Weight: 687.869
• European Community (EC) Number: 223-495-7
• Metabolomics Workbench ID: 21280
• NCI Thesaurus Code: C61864
• Wikipedia: Oleandomycin
• Mol file: 3922-90-5.mol

Synonyms:Oleandomycin;Oleandomycin Phosphate;Phosphate, Oleandomycin

Chemical Property of CID 20407245

Chemical Property:

• Vapor Pressure: 8.49E-30mmHg at 25°C
• Melting Point: 110 °C (decomp)
• Boiling Point: 802.6°C at 760 mmHg
• PKA: pKa 8.84(H2O,t =25,I=0.167) (Uncertain)
• Flash Point: 439.2°C
• PSA: 165.98000
• Density: 1.21g/cm³
• LogP: 1.90850
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 687.41937638
• Heavy Atom Count: 48
• Complexity: 1090

Purity/Quality:

98%Min ^*data from raw suppliers

Oleandomycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Low toxicity by ingestion.
• Hazard Codes: Low toxicity by ingestion.

MSDS Files:

Useful:

• Canonical SMILES: CC1CC(C(C(O1)OC2C(CC3(CO3)C(=O)C(C(C(C(OC(=O)C(C(C2C)OC4CC(C(C(O4)C)O)OC)C)C)C)O)C)C)O)N(C)C
• Isomeric SMILES: C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@@H](C[C@@]3(CO3)C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)O)OC)C)C)C)O)C)C)O)N(C)C
• Uses: Antibiotic substance produced by Streptomyces antibioticus no. ATCC 11891. Antibacterial. Oleandomycin is a 16-membered macrocyclic lactone, discovered in the 1950s, with broad spectrum antibacterial activity. Oleandomycin was developed as a human pharmaceutical but was regarded as less active than comparable products such as erythromycin and is today only available in combination with other antibiotics.
• Therapeutic Function: Antibiotic

Technology Process of CID 20407245

There total 9 articles about CID 20407245 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:

C27H39BrO7 (119870-69-8) → oleandomycin (3922-90-5,7562-59-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridinium dichromate / CH₂Cl₂ / 8 h / Ambient temperature

2: H₂ / 20percent Pd(OH)2-C / dioxane / 1 h / Ambient temperature

3: 42 percent / silver triflate, MS 4A / toluene; CH₂Cl₂ / 5 h / Ambient temperature

With dipyridinium dichromate; hydrogen; silver trifluoromethanesulfonate; palladium hydroxide - carbon; In 1,4-dioxane; dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)80397-4

Reference yield:

(1S,2R,5R,6R,7R,8R,9R,12S,13S,17R)-15-(4-Bromo-phenyl)-7,9-dihydroxy-2,5,6,8,12,17-hexamethyl-10-methylene-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one (119887-69-3) → oleandomycin (3922-90-5,7562-59-6)

Guidance literature:

Multi-step reaction with 5 steps

1: m-chloroperbenzoic acid / CCl₄ / 2 h / Ambient temperature

2: pyridinium dichromate / CH₂Cl₂ / 8 h / Ambient temperature

3: H₂ / 20percent Pd(OH)2-C / dioxane / 1 h / Ambient temperature

4: 42 percent / silver triflate, MS 4A / toluene; CH₂Cl₂ / 5 h / Ambient temperature

With dipyridinium dichromate; hydrogen; silver trifluoromethanesulfonate; 3-chloro-benzenecarboperoxoic acid; palladium hydroxide - carbon; In 1,4-dioxane; tetrachloromethane; dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)80397-4

Reference yield:

C27H37BrO7 (119870-70-1) → oleandomycin (3922-90-5,7562-59-6)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 20percent Pd(OH)2-C / dioxane / 1 h / Ambient temperature

2: 42 percent / silver triflate, MS 4A / toluene; CH₂Cl₂ / 5 h / Ambient temperature

With hydrogen; silver trifluoromethanesulfonate; palladium hydroxide - carbon; In 1,4-dioxane; dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)80397-4

upstream raw materials:

Carbonic acid benzyl ester (2S,3S,4S)-4-methoxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester

Acetic acid (2S,3R,4S,6R)-2-((3R,5R,6S,7R,8R,11R,12S,13S,14S,15S)-6,12-dihydroxy-5,7,8,11,13,15-hexamethyl-4,10-dioxo-1,9-dioxa-spiro[2.13]hexadec-14-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester

Oleandolide

C₂₇H₃₉BrO₇

Downstream raw materials:

2'-acetyl-3'-de(dimethylamino)-8,8a-deepoxy-3',4'-dehydro-8a-phenylthiooleandomycin

2'-acetyl-3'-de(dimethylamino)-8,8a-deepoxy-3',4'-dehydro-3-deoleandrosyl-8-phenylthiooleandomycin

3'-de(dimethylamino)-8,8a-deepoxy-3',4'-dehydro-3-deoleandrosyl-8-phenylthiooleandomycin

C₃₁H₄₁⁽²⁾H₄BrO₈

Refernces