Erythronolide B

Base Information

• Chemical Name: Erythronolide B
• CAS No.: 3225-82-9
• Molecular Formula: C₂₁H₃₈O₇
• Molecular Weight: 402.529
• UNII: H8F3GHM6EA
• Nikkaji Number: J14.506H
• Wikidata: Q27103435
• Metabolomics Workbench ID: 51540
• Mol file: 3225-82-9.mol

Synonyms:erythronolide B;erythronolide-B

Chemical Property of Erythronolide B

Chemical Property:

• Vapor Pressure: 1.12E-15mmHg at 25°C
• Boiling Point: 576.2°Cat760mmHg
• PKA: 13.81±0.70(Predicted)
• Flash Point: 192.2°C
• PSA: 124.29000
• Density: 1.069g/cm³
• LogP: 1.29520
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 402.26175355
• Heavy Atom Count: 28
• Complexity: 551

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
• Isomeric SMILES: CC[C@@H]1[C@@H]([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

Technology Process of Erythronolide B

There total 36 articles about Erythronolide B 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: 65.0%

3,5-O-benzylideneerythronolide B (123107-83-5) → Erythronolide B (3225-82-9,19270-26-9,24784-66-5)

Guidance literature:

With acetic acid; at 50 ℃; for 3h;

DOI:10.1007/BF00953635

Reference yield:

3,5-O-benzylidene-(9S)-dihydroerythronolide B (56014-68-7,56085-63-3,114182-42-2) → Erythronolide B (3225-82-9,19270-26-9,24784-66-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / PCC, molecular sieves (3 Angstroem) / CH₂Cl₂ / 0.5 h / 0 °C

2: 65 percent / 80 percent AcOH / 3 h / 50 °C

With 3 A molecular sieve; acetic acid; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/S0040-4020(01)81090-5

Reference yield:

3,5-isopropylidene-9-11-O-(p-methoxybenzylidene)-9(S)-dihydroerythronolide B (114137-94-9) → Erythronolide B (3225-82-9,19270-26-9,24784-66-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / TFA / acetonitrile; H₂O / 0.08 h / Ambient temperature

2: 48 percent / (+/-)-camphor-10-sulfonic acid / CH₂Cl₂ / 5.5 h / -10 °C

3: 71 percent / PCC, molecular sieves (3 Angstroem) / CH₂Cl₂ / 0.5 h / 0 °C

4: 65 percent / 80 percent AcOH / 3 h / 50 °C

With 3 A molecular sieve; camphor-10-sulfonic acid; acetic acid; pyridinium chlorochromate; trifluoroacetic acid; In dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4020(01)81090-5

upstream raw materials:

3,5-O-benzylideneerythronolide B

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

(3R,4S,5R,6S,7S,9R,11R,12S,13R,14R)-14-ethyl-4,6,12-trihydroxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione

[(4S,5S,6R)-2,2,5-Trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-methanol

Downstream raw materials:

O³,O⁵-phenylboranediyl-12-deoxy-erythronolide-A

10-epi-erythronolide B

O¹¹-acetyl-O³,O⁵-phenylboranediyl-12-deoxy-erythronolide-A

O¹¹-benzoyl-O³,O⁵-phenylboranediyl-12-deoxy-erythronolide-A

Refernces

Synthesis of 5 acetoxy 9 oxotridecanolactone. A model for erythronolide B

10.1016/S0040-4039(01)91879-9

The study details the synthesis of 5-acetoxy-9-oxotridecanolactone as a model for erythronolide B, the aglycone of erythromycin B. The researchers aimed to develop a route to 5-acetoxy-13-hydroxy-9-oxotridecanoic acid, with the intention of lactonization at the final stage of macrolide synthesis. The synthesis involved assembling a thirteen-carbon backbone from two cyclopentanoid and one propanoid unit. Key steps included alkylation of the potassio salt of cyclopentanone carboxylic ester with 1,3-dibromopropane, decarboxylation with HBr, Baeyer-Villiger oxidation using CF3CO3H, and further alkylation and decarboxylation steps. The study also involved protecting and unmasking the cyclopentanone carbonyl group, reduction of an ester group with LiAlH4, and oxidation with Collins' reagent. The final lactonization was achieved using p-toluenesulfonyl chloride and Et3N, or alternatively, 1,1'-carbonyldiimidazole and sodium t-amylate. The synthetic route demonstrated potential applicability to erythronolide and other macrolide systems.