(1R,3S,8R,11S,13S)-11-acetoxy-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadecane

Base Information

• Chemical Name: (1R,3S,8R,11S,13S)-11-acetoxy-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadecane
• CAS No.: 250140-08-0
• Molecular Formula: C₂₃H₃₀O₇S
• Molecular Weight: 450.553
• Mol file: 250140-08-0.mol

Synonyms:

Chemical Property of (1R,3S,8R,11S,13S)-11-acetoxy-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,8R,11S,13S)-11-acetoxy-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadecane

There total 13 articles about (1R,3S,8R,11S,13S)-11-acetoxy-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadecane 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:

(2R,3S)-{3-[(2S,3R)-2-vinyloxan-3-yloxy]oxan-2-yl}methanol (161638-76-2) → (1R,3S,8R,11S,13S)-11-acetoxy-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.03,8]heptadecane (250140-08-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: DMAP; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C

2.2: aq. H₂O₂; aq. NaHCO₃ / tetrahydrofuran; ethanol / 0.5 h / 20 °C

3.1: imidazole / dimethylformamide / 0.5 h / 0 °C

4.1: DIBALH / CH₂Cl₂; toluene / 0.5 h / -78 °C

5.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 0.5 h / 0 °C

6.1: tetrahydrofuran; diethyl ether / -78 - 0 °C

7.1: 69 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: i-Pr₂NEt / CH₂Cl₂ / 0.75 h / -10 °C

9.1: N-bromosuccinimide / tetrahydrofuran / 0.33 h / 0 °C

10.1: camphorsulfonic acid / CH₂Cl₂; methanol / 0.75 h / 0 °C

11.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 0.67 h / 0 °C

12.1: SmI₂ / tetrahydrofuran / 1 h / -78 °C

12.2: DMAP / tetrahydrofuran / 0.67 h / 0 °C

13.1: NaBH₄ / methanol / 0.17 h / 0 °C

14.1: DMAP / acetonitrile / 0.5 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; N-Bromosuccinimide; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Acetylation / 2.1: Addition / 2.2: Oxidation / 3.1: Substitution / 4.1: Reduction / 5.1: Oxidation / 6.1: Addition / 7.1: Oxidation / 8.1: Substitution / 9.1: Bromination / 10.1: desilylation / 11.1: Oxidation / 12.1: Cyclization / 12.2: Acetylation / 13.1: Reduction / 14.1: Acylation;

DOI:10.1016/S0040-4020(99)00620-1

Reference yield:

(2R,3S)-(3-{(2S,3R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]oxan-3-yloxy}oxan-2-yl)methanol (250140-02-4) → (1R,3S,8R,11S,13S)-11-acetoxy-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.03,8]heptadecane (250140-08-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 0.5 h / 0 °C

2.1: tetrahydrofuran; diethyl ether / -78 - 0 °C

3.1: 69 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: i-Pr₂NEt / CH₂Cl₂ / 0.75 h / -10 °C

5.1: N-bromosuccinimide / tetrahydrofuran / 0.33 h / 0 °C

6.1: camphorsulfonic acid / CH₂Cl₂; methanol / 0.75 h / 0 °C

7.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 0.67 h / 0 °C

8.1: SmI₂ / tetrahydrofuran / 1 h / -78 °C

8.2: DMAP / tetrahydrofuran / 0.67 h / 0 °C

9.1: NaBH₄ / methanol / 0.17 h / 0 °C

10.1: DMAP / acetonitrile / 0.5 h / 20 °C

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; samarium diiodide; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; 1.1: Oxidation / 2.1: Addition / 3.1: Oxidation / 4.1: Substitution / 5.1: Bromination / 6.1: desilylation / 7.1: Oxidation / 8.1: Cyclization / 8.2: Acetylation / 9.1: Reduction / 10.1: Acylation;

DOI:10.1016/S0040-4020(99)00620-1

Reference yield:

1-((2R,3S)-3-{(2S,3R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-3-yloxy}-tetrahydro-pyran-2-yl)-ethanol (250140-03-5) → (1R,3S,8R,11S,13S)-11-acetoxy-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.03,8]heptadecane (250140-08-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 69 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: i-Pr₂NEt / CH₂Cl₂ / 0.75 h / -10 °C

3.1: N-bromosuccinimide / tetrahydrofuran / 0.33 h / 0 °C

4.1: camphorsulfonic acid / CH₂Cl₂; methanol / 0.75 h / 0 °C

5.1: DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 0.67 h / 0 °C

6.1: SmI₂ / tetrahydrofuran / 1 h / -78 °C

6.2: DMAP / tetrahydrofuran / 0.67 h / 0 °C

7.1: NaBH₄ / methanol / 0.17 h / 0 °C

8.1: DMAP / acetonitrile / 0.5 h / 20 °C

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; samarium diiodide; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1.1: Oxidation / 2.1: Substitution / 3.1: Bromination / 4.1: desilylation / 5.1: Oxidation / 6.1: Cyclization / 6.2: Acetylation / 7.1: Reduction / 8.1: Acylation;

DOI:10.1016/S0040-4020(99)00620-1

upstream raw materials:

(2R,3S)-{3-[(2S,3R)-2-vinyloxan-3-yloxy]oxan-2-yl}methanol

(2R,3S)-(3-{(2S,3R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]oxan-3-yloxy}oxan-2-yl)methanol

1-((2R,3S)-3-{(2S,3R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-3-yloxy}-tetrahydro-pyran-2-yl)-ethanol

(2S,3S)-2-(bromoacetyl)-3-[(2S,3R)-2-(2-hydroxyethyl)oxan-3-yloxy]oxane