16-Deacetylfusidic Acid gamma-Lactone

Base Information

• Chemical Name: 16-Deacetylfusidic Acid gamma-Lactone
• CAS No.: 4701-54-6
• Molecular Formula: C₂₉H₄₄O₄
• Molecular Weight: 456.666

Synonyms:16-DAFAL;16-O-deacetylfusidic acid lactone;16-O-desacetylfusidic acid lactone

Chemical Property of 16-Deacetylfusidic Acid gamma-Lactone

Chemical Property:

• Vapor Pressure: 5.17E-17mmHg at 25°C
• Boiling Point: 602.2°Cat760mmHg
• PKA: 14.69±0.70(Predicted)
• Flash Point: 193.2°C
• PSA: 66.76000
• Density: 1.14g/cm³
• LogP: 5.57520
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 456.32395988
• Heavy Atom Count: 33
• Complexity: 899

Purity/Quality:

99%, ^*data from raw suppliers

16-DeacetylfusidicAcidγ-Lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CCC3(C(C2(CCC1O)C)C(CC4C3(CC5C4=C(C(=O)O5)CCC=C(C)C)C)O)C
• Isomeric SMILES: C[C@@H]1[C@@H](CC[C@]2(C1CC[C@]3([C@H]2[C@@H](C[C@@H]4[C@@]3(C[C@H]5C4=C(C(=O)O5)CCC=C(C)C)C)O)C)C)O
• Uses: 16-Deacetylfusidic Acid γ-Lactone is a metabolite of the drug Fusidic Acid (F865500). Fusidic acid is a bacteriostatic antibiotic. Fusidic Acid suppresses nitric oxide lysis of pancreatic islet cells. Inhibits protein synthesis in prokaryotes by inhibiting the ribosome-dependent activity of G factor and translocation of peptidyl-tRNA.

Technology Process of 16-Deacetylfusidic Acid gamma-Lactone

There total 3 articles about 16-Deacetylfusidic Acid gamma-Lactone 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: 96.0%

fusidine (3482-49-3,4680-36-8,6990-06-3,19030-42-3,107380-53-0) → (1S,2R,4aS,4bS,5R,6aR,9aS,10aS,10bS,12aS)-2,5-dihydroxy-1,4a,10a,10b-tetramethyl-7-(4-methylpent-3-en-1-yl)-1,2,3,4,4a,4b,5,6,6a,9a,10,10a,10b,11,12,12a-hexadecahydro-8H-naphtho[2′,1′:4,5]indeno[2,1-b]-furan-8-one (4701-54-6)

Guidance literature:

With sodium hydroxide; In ethanol; Heating;

DOI:10.1016/S0960-894X(02)00797-7

Reference yield:

fusidic acid sodium salt → (1S,2R,4aS,4bS,5R,6aR,9aS,10aS,10bS,12aS)-2,5-dihydroxy-1,4a,10a,10b-tetramethyl-7-(4-methylpent-3-en-1-yl)-1,2,3,4,4a,4b,5,6,6a,9a,10,10a,10b,11,12,12a-hexadecahydro-8H-naphtho[2′,1′:4,5]indeno[2,1-b]-furan-8-one (4701-54-6)

Guidance literature:

With potassium hydroxide; In methanol; for 7h; pH=11; Heating;

DOI:10.7164/antibiotics.52.335

Reference yield:

→ (1S,2R,4aS,4bS,5R,6aR,10aS,10bS,12aS)-2,5-Dihydroxy-1,4a,10a,10b-tetramethyl-7-(4-methyl-pent-3-enyl)-1,2,3,4,4a,4b,5,6,6a,9a,10,10a,10b,11,12,12a-hexadecahydro-9-oxa-pentaleno[2,1-a]phenanthren-8-one (4701-54-6,13011-12-6,79813-91-5,137120-27-5)

Guidance literature:

Benzolsolvat der Fusidinsaeure (IVa) 1) KOH 2) Eisessig;

upstream raw materials:

fusidine

Downstream raw materials:

17S,20R-dihydrofusidic acid lactone

C₄₉H₇₆O₄Si₂

C₅₁H₇₈O₅Si₂

17S,20S-dihydrofusidic acid lactone

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