Antibiotic SL-2266

Base Information

• Chemical Name: Antibiotic SL-2266
• CAS No.: 11076-17-8
• Molecular Formula: C₂₇H₄₀O₈
• Molecular Weight: 492.61
• DSSTox Substance ID: DTXSID80911847
• Mol file: 11076-17-8.mol

Synonyms:sordarin;sordarin B

Chemical Property of Antibiotic SL-2266

Chemical Property:

• Vapor Pressure: 1.58E-18mmHg at 25°C
• Boiling Point: 630.2°Cat760mmHg
• Flash Point: 205°C
• PSA: 122.52000
• Density: 1.29g/cm³
• LogP: 2.40920
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 492.27231823
• Heavy Atom Count: 35
• Complexity: 917

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2C1CC3(C4CC2(C3(C(=C4)C(C)C)C(=O)O)C=O)COC5C(C(C(C(O5)C)OC)O)O
• Isomeric SMILES: C[C@@H]1CC[C@@H]2[C@@H]1C[C@@]3([C@@H]4C[C@]2([C@]3(C(=C4)C(C)C)C(=O)O)C=O)CO[C@H]5[C@H]([C@@H]([C@@H]([C@H](O5)C)OC)O)O

Technology Process of Antibiotic SL-2266

There total 17 articles about Antibiotic SL-2266 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: 95.0%

C29H44O8 (896437-60-8) → (-)-sordarin (11076-17-8)

Guidance literature:

With sodium 1-propanethiolate; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃; for 12h;

DOI:10.1021/ja060408h

Reference yield:

(2R,3R,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-one (896436-14-9) → (-)-sordarin (11076-17-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 77 percent / NaBH₄ / methanol / 0.5 h / 0 °C

2.1: DMAP; pyridine / 2 h / 20 °C

3.1: 96 percent / NBS / acetone; H₂O / 1 h / 20 °C

4.1: (diethylamino)sulfur trifluoride / CH₂Cl₂ / 0.2 h / 20 °C

5.1: MS 4A; AgClO₄; SnCl₂ / diethyl ether / 5.5 h / 20 °C

5.2: 79 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

6.1: 95 percent / EtONa / ethanol / 4 h / 20 °C

7.1: 95 percent / n-PrSNa / hexamethylphosphoric acid triamide / 12 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; N-Bromosuccinimide; diethylamino-sulfur trifluoride; sodium ethanolate; silver perchlorate; tin(ll) chloride; sodium 1-propanethiolate; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; water; acetone;

DOI:10.1021/ja060408h

Reference yield:

(2R,3S,4R,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol (896436-23-0) → (-)-sordarin (11076-17-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DMAP; pyridine / 2 h / 20 °C

2.1: 96 percent / NBS / acetone; H₂O / 1 h / 20 °C

3.1: (diethylamino)sulfur trifluoride / CH₂Cl₂ / 0.2 h / 20 °C

4.1: MS 4A; AgClO₄; SnCl₂ / diethyl ether / 5.5 h / 20 °C

4.2: 79 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

5.1: 95 percent / EtONa / ethanol / 4 h / 20 °C

6.1: 95 percent / n-PrSNa / hexamethylphosphoric acid triamide / 12 h / 20 °C

With pyridine; dmap; N-Bromosuccinimide; diethylamino-sulfur trifluoride; sodium ethanolate; silver perchlorate; tin(ll) chloride; sodium 1-propanethiolate; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; water; acetone;

DOI:10.1021/ja060408h

upstream raw materials:

C₂₉H₄₄O₈

(2R,3R,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-one

(2R,3S,4R,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

(2R,3S,4S,5S,6R)-3-Methoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

Refernces