6-deoxyerythronolide B

Base Information

• Chemical Name: 6-deoxyerythronolide B
• CAS No.: 15797-36-1
• Molecular Formula: C21H38 O6
• Molecular Weight: 386.52
• DSSTox Substance ID: DTXSID50935833
• Nikkaji Number: J96.988E
• Wikidata: Q27094923
• Metabolomics Workbench ID: 21275
• Mol file: 15797-36-1.mol

Synonyms:3,5,11-trihydroxyerythranolid-9-one;6-deoxyerythronolide B

Chemical Property of 6-deoxyerythronolide B

Chemical Property:

• Vapor Pressure: 5.92E-15mmHg at 25°C
• Boiling Point: 561.7°C at 760 mmHg
• Flash Point: 187.5°C
• PSA: 104.06000
• Density: 1.014g/cm³
• LogP: 2.18030
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 386.26683893
• Heavy Atom Count: 27
• Complexity: 507

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

Technology Process of 6-deoxyerythronolide B

There total 35 articles about 6-deoxyerythronolide 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: 94.0%

(1S,2R,5R,6R,7S,8R,10R,12S,13S,17R)-5-Ethyl-7-hydroxy-2,6,8,10,12,15,15,17-octamethyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecane-3,9-dione (77405-56-2) → (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 (15797-36-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1021/ja9806128

Reference yield: 93.0%

(1S,2R,5R,6S,7S,8R,10R,12S,13S,15S,17R)-7-(benzyloxy)-5-ethyl-15-(4-methoxyphenyl)-2,6,8,10,12,17-hexamethyl-4,14,16-trioxabicyclo[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 (15797-36-1)

Guidance literature:

With palladium diacetate; In isopropyl alcohol; at 25 ℃;

DOI:10.1021/ja4008722

Reference yield:

(1S,2R,4S,5S,9S,10R,13R,14S,15S,17R,19S,20R)-13-Ethyl-17-(4-methoxy-phenyl)-2,4,7,7,10,14,19,20-octamethyl-6,8,12,16,18-pentaoxa-tricyclo[13.3.1.15,9]icosan-11-one (186489-81-6) → (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 (15797-36-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / H₂ / Pd(OH)2 / propan-2-ol / 13 h / Ambient temperature

2: 76 percent / PCC, 4 A sieves / CH₂Cl₂ / 1 h / Ambient temperature

3: 94 percent / aq. HCl / tetrahydrofuran / 4 h / Ambient temperature

With hydrogenchloride; 4 A molecular sieve; hydrogen; pyridinium chlorochromate; palladium dihydroxide; In tetrahydrofuran; dichloromethane; isopropyl alcohol;

DOI:10.1021/ja9806128

upstream raw materials:

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

sodium proprionate

(2S,3R)-S-(2-methyl-3-hydroxypentanoyl)-N-acetylcysteamine

(9S)-6,12-Dideoxy-9-deoxo-9-hydroxy-3,5-O-(1-methylethylidene)erythronolide A ((9S)-Dihydro-6-deoxy-erythronolide B) 3,5-Acetonide

Downstream raw materials:

Erythronolide B

Refernces

The Role of Serine-246 in Cytochrome P450eryF-Catalyzed Hydroxylation of 6-Deoxyerythronolide B

10.1006/bioo.2000.1187

This study investigates the role of serine-246 in the cytochrome P450eryF-catalyzed hydroxylation of 6-deoxyerythronolide B. The researchers constructed and characterized three mutant forms of P450eryF (A245S, S246A, and A245S/S246A) to assess the role of hydroxyl groups around the active site in the proton delivery system. They found that changes in the hydrogen bonding environment correlated with decreased catalytic activity and increased uncoupling. The results suggest that serine-246 participates in the proton shuttling pathway and supports the hypothesis that the C-5 hydroxyl group of the substrate is involved in the acid-catalyzed dioxygen bond cleavage reaction. The study provides insights into the catalytic mechanism of P450eryF and highlights the importance of the hydrogen bonding network in maintaining its catalytic activity.

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