Desoleandomycin

Base Information

• Chemical Name: Desoleandomycin
• CAS No.: 4166-78-3
• Molecular Formula: C₂₈H₄₉NO₉
• Molecular Weight: 543.698
• DSSTox Substance ID: DTXSID80961887
• Mol file: 4166-78-3.mol

Synonyms:deoleandrosyl-oleandomycin

Chemical Property of Desoleandomycin

Chemical Property:

• Vapor Pressure: 4.2E-23mmHg at 25°C
• Boiling Point: 707°C at 760 mmHg
• Flash Point: 381.4°C
• PSA: 138.29000
• Density: 1.19g/cm³
• LogP: 1.37340
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 543.34073214
• Heavy Atom Count: 38
• Complexity: 839

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C(C(O1)OC2C(CC3(CO3)C(=O)C(C(C(C(OC(=O)C(C(C2C)O)C)C)C)O)C)C)O)N(C)C

Technology Process of Desoleandomycin

There total 9 articles about Desoleandomycin 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%

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 (119870-73-4) → deoleandrosyl-oleandomycin (4166-78-3)

Guidance literature:

With methanol; triethylamine; for 10h; Ambient temperature;

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

Reference yield: 45.0%

oleandomycin (3922-90-5,7562-59-6) → deoleandrosyl-oleandomycin (4166-78-3)

Guidance literature:

With dichloro-acetic acid; at 60 ℃; for 18h;

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

Reference yield:

C27H39BrO7 (119870-69-8) → deoleandrosyl-oleandomycin (4166-78-3)

Guidance literature:

Multi-step reaction with 5 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

5: 45 percent / 7percent CHCl₂COOH / 18 h / 60 °C

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

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

upstream raw materials:

oleandomycin

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

sulfuric acid

Oleandolide

Refernces