(2S,3S,5R,6S,8R,9R,10S,11S)-8-[1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl]-8,10-dihydroxy-3,5,9,11-tetramethyl-2-[(2S)-3-oxopentan-2-yl]-1,7-dioxaspiro[5.5]undecan-4-one (non-preferred name)

Base Information

• Chemical Name: (2S,3S,5R,6S,8R,9R,10S,11S)-8-[1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl]-8,10-dihydroxy-3,5,9,11-tetramethyl-2-[(2S)-3-oxopentan-2-yl]-1,7-dioxaspiro[5.5]undecan-4-one (non-preferred name)
• CAS No.: 92125-68-3
• Molecular Formula: C₂₉H₄₄O₈
• Molecular Weight: 520.664
• Mol file: 92125-68-3.mol

Synonyms:

Chemical Property of (2S,3S,5R,6S,8R,9R,10S,11S)-8-[1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl]-8,10-dihydroxy-3,5,9,11-tetramethyl-2-[(2S)-3-oxopentan-2-yl]-1,7-dioxaspiro[5.5]undecan-4-one (non-preferred name)

Chemical Property:

• Vapor Pressure: 3.92E-21mmHg at 25°C
• Boiling Point: 675.3°Cat760mmHg
• Flash Point: 214.6°C
• Density: 1.17g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3S,5R,6S,8R,9R,10S,11S)-8-[1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl]-8,10-dihydroxy-3,5,9,11-tetramethyl-2-[(2S)-3-oxopentan-2-yl]-1,7-dioxaspiro[5.5]undecan-4-one (non-preferred name)

There total 8 articles about (2S,3S,5R,6S,8R,9R,10S,11S)-8-[1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)ethyl]-8,10-dihydroxy-3,5,9,11-tetramethyl-2-[(2S)-3-oxopentan-2-yl]-1,7-dioxaspiro[5.5]undecan-4-one (non-preferred name) 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: 50.0%

ent-caloundrin B (1362830-21-4) → siphonarin B (92125-68-3)

Guidance literature:

With 1H-imidazole; In chloroform; at 20 ℃; for 24h;

DOI:10.1021/ol300432y

Reference yield:

(2R)-2-[(1R,3R,5S,7R,8R,9R,10R)-3-ethyl-8,9,10-trimethyl-1-trimethylsilyloxy-2,4,6-trioxatricyclo[3.3.1.1(3,7)]dec-5-yl]pentan-3-ol → siphonarin B (92125-68-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 14 h / 20 °C / Inert atmosphere

2.1: lithium tert-butyl-trimethylsilylamide / tetrahydrofuran; hexane / 0.17 h / 0 °C / Inert atmosphere

2.2: 0.25 h / -78 °C / Inert atmosphere

2.3: 7 h / -78 °C / Inert atmosphere

3.1: methanol; diethyl methoxy borane / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere

3.2: 3.17 h / -78 - 0 °C / Inert atmosphere

3.3: 1.08 h / 0 - 20 °C / aq. phosphate buffer

4.1: 2,6-dimethylpyridine / dichloromethane / 0.1 h / -50 °C / Inert atmosphere

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 13 h / 20 °C / Inert atmosphere

6.1: pyridine; water; pyridine hydrogenfluoride / tetrahydrofuran / 2 h / 20 °C

7.1: 1H-imidazole / chloroform / 24 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; methanol; diethyl methoxy borane; water; lithium tert-butyl-trimethylsilylamide; pyridine hydrogenfluoride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; chloroform; dimethyl sulfoxide; toluene;

DOI:10.1021/ol300432y

Reference yield:

(R)-2-[(1R,3R,5S,7R,8R,9R,10R)-3-ethyl-8,9,10-trimethy-1-trimethylsilyloxy-2,4,6-trioxatricyclo[3.3.1.1(3,7)]dec-5-yl]pentan-3-one (1362829-96-6) → siphonarin B (92125-68-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium tert-butyl-trimethylsilylamide / tetrahydrofuran; hexane / 0.17 h / 0 °C / Inert atmosphere

1.2: 0.25 h / -78 °C / Inert atmosphere

1.3: 7 h / -78 °C / Inert atmosphere

2.1: methanol; diethyl methoxy borane / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere

2.2: 3.17 h / -78 - 0 °C / Inert atmosphere

2.3: 1.08 h / 0 - 20 °C / aq. phosphate buffer

3.1: 2,6-dimethylpyridine / dichloromethane / 0.1 h / -50 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 13 h / 20 °C / Inert atmosphere

5.1: pyridine; water; pyridine hydrogenfluoride / tetrahydrofuran / 2 h / 20 °C

6.1: 1H-imidazole / chloroform / 24 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; methanol; diethyl methoxy borane; water; lithium tert-butyl-trimethylsilylamide; pyridine hydrogenfluoride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; chloroform; dimethyl sulfoxide; toluene;

DOI:10.1021/ol300432y

upstream raw materials:

(R)-2-[(1R,3R,5S,7R,8R,9R,10R)-3-ethyl-8,9,10-trimethy-1-trimethylsilyloxy-2,4,6-trioxatricyclo[3.3.1.1(3,7)]dec-5-yl]pentan-3-one

ent-(13S)-11-didehydro-13-dihydro-7-O-(trimethylsilyl)caloundrin B

ent-(13R)-13-dihydro-7-O-(trimethylsilyl)caloundrin B

ent-(13S)-13-dihydro-11-O-(triethylsilyl)-7-O-(trimethylsilyl)caloundrin B