Erythronolide A

Base Information

• Chemical Name: Erythronolide A
• CAS No.: 26754-37-0
• Molecular Formula: C21H38 O8
• Molecular Weight: 418.528
• DSSTox Substance ID: DTXSID40181266
• Nikkaji Number: J510.519F
• Wikidata: Q27121373
• Metabolomics Workbench ID: 57118
• Mol file: 26754-37-0.mol

Synonyms:(9S)-dihydroerythronolide A;erythronolide A;erythronolide-A

Chemical Property of Erythronolide A

Chemical Property:

• Vapor Pressure: 2.06E-16mmHg at 25°C
• Boiling Point: 590.7°Cat760mmHg
• Flash Point: 196.7°C
• PSA: 144.52000
• Density: 1.125g/cm³
• LogP: 0.41010
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 418.25666817
• Heavy Atom Count: 29
• Complexity: 595

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)O)C)O)(C)O)C)C)O)(C)O
• Isomeric SMILES: CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O)C)O)(C)O)C)C)O)(C)O

Technology Process of Erythronolide A

There total 74 articles about Erythronolide A 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: 82.0%

(1S,2R,5R,6S,7R,8R,10R,12R,13R,17S)-5-Ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecane-3,9-dione (105545-16-2,124990-95-0) → erythronolide A (26754-37-0)

Guidance literature:

With hydrogen; In methanol; for 0.5h; under 760 Torr;

DOI:10.1016/S0040-4039(00)84383-X

Reference yield: 40.0%

3,5-O-benzylidene erythronolide A → erythronolide A (26754-37-0)

Guidance literature:

With palladium diacetate; hydrogen; In methanol; water; at 20 ℃; for 6h;

DOI:10.1002/anie.200500172

Reference yield:

erythromycin (114-07-8) → erythronolide A (26754-37-0)

Guidance literature:

With hydrogenchloride; In dichloromethane; water; at 50 ℃; for 24h;

upstream raw materials:

(1S,2R,5R,6S,7R,8R,10R,12R,13R,17S)-5-Ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecane-3,9-dione

(1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-2,9-dihydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one

(1R,2R,4R,8R,9R,10R,13R,14S,18S,19S)-10-ethyl-9-hydroxy-2,4,9,13,18,19-hexamethyl-16-phenyl-2-[(triethylsilyl)oxy]-7,11,15,17-tetraoxa-6-azatricyclo[12.3.1.1^5,8]nonadec-5-en-12-one

3,5-O-benzylidene-1,4,6-trideoxy-2-C-((2R)-2-{(4S,5R)-5-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-4-methyl-4,5-dihydroisoxazol-3-yl}propyl)-4,6-dimethyl-2-O-(triethylsilyl)-L-glycero-D-gulo-heptitol

Downstream raw materials:

(9R)-dihydroerythronolide

9S-Dihydroerythronolide A aglycon

Refernces

• 1、 Muri, Dieter,Carreira, Erick M.. "Stereoselective synthesis of erythronolide A via nitrile oxide cycloadditions and related studies". experimental part. p. 8695 - 8712. Retrieved 2010/01/15.
• 2、 Nakata,Arai,Tomooka,Ohsawa,Kinoshita. "Total synthesis of erythronolide A". . p. 2618 - 2635. Retrieved 2007/10/02.