(1S,3S,8S,9R,13R)-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadec-10-ene

Base Information

• Chemical Name: (1S,3S,8S,9R,13R)-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadec-10-ene
• CAS No.: 250139-95-8
• Molecular Formula: C₂₁H₂₆O₅S
• Molecular Weight: 390.5

Synonyms:(1S,3S,8S,9R,13R)-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadec-10-ene

Chemical Property of (1S,3S,8S,9R,13R)-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadec-10-ene

Chemical Property:

Purity/Quality:

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• Hazard Codes: 

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Technology Process of (1S,3S,8S,9R,13R)-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadec-10-ene

There total 14 articles about (1S,3S,8S,9R,13R)-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadec-10-ene 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: 93.0%

phenylcarbonochloridothioate (1005-56-7) + (1S,3S,8S,9R,13R)-9-hydroxy-2,7,14-trioxatricyclo[11.4.0.03,8]heptadec-10-ene (250139-94-7) → (1S,3S,8S,9R,13R)-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.03,8]heptadec-10-ene (250139-95-8)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃; for 4h;

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

Reference yield:

Tributyl-{(Z)-3-[(2R,4aR,8aS)-3-(hexahydro-pyrano[3,2-d][1,3]dioxin-2-yl)-propoxy]-allyl}-stannane → (1S,3S,8S,9R,13R)-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.03,8]heptadec-10-ene (250139-95-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 60 percent / TiCl₃(O-i-Pr) / CH₂Cl₂; toluene / 0.25 h / -78 °C

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

3.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C

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

4.1: imidazole / dimethylformamide / 20 °C

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

6.1: DMSO; Et₃n; SO₃*Py / CH₂Cl₂ / 0.5 h / 0 °C

7.1: tetrahydrofuran; diethyl ether / 0.67 h / -78 °C

8.1: 84 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

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

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

11.1: camphorsulfonic acid / CH₂Cl₂; methanol / 0.67 h / 0 °C

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

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

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

14.1: 84 percent / BF₃*OEt₂ / acetonitrile / 0 - 20 °C

15.1: 79 percent / DIBALH / CH₂Cl₂; toluene / 0.5 h / -78 °C

16.1: 93 percent / DMAP / acetonitrile / 4 h / 20 °C

With 1H-imidazole; dmap; N-Bromosuccinimide; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; oxalyl dichloride; titanium(IV) trichloride isopropoxide; pyridine-SO₃ complex; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Cyclization / 2.1: Acetylation / 3.1: Addition / 3.2: Oxidation / 4.1: Substitution / 5.1: Reduction / 6.1: Oxidation / 7.1: Addition / 8.1: Oxidation / 9.1: Substitution / 10.1: Bromination / 11.1: desilylation / 12.1: Oxidation / 13.1: Cyclization / 13.2: Acetylation / 14.1: Elimination / 15.1: Reduction / 16.1: Acylation;

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

Reference yield:

(2R,3S)-{3-[(2R,3S)-2-vinyloxan-3-yloxy]oxan-2-yl}methanol (250139-86-7) → (1S,3S,8S,9R,13R)-9-(phenoxythiocarbonyloxy)-2,7,14-trioxatricyclo[11.4.0.03,8]heptadec-10-ene (250139-95-8)

Guidance literature:

Multi-step reaction with 15 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 / 20 °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 / 0.67 h / -78 °C

7.1: 84 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 / 0.67 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: 84 percent / BF₃*OEt₂ / acetonitrile / 0 - 20 °C

14.1: 79 percent / DIBALH / CH₂Cl₂; toluene / 0.5 h / -78 °C

15.1: 93 percent / DMAP / acetonitrile / 4 h / 20 °C

With 1H-imidazole; dmap; N-Bromosuccinimide; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; 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: Elimination / 14.1: Reduction / 15.1: Acylation;

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

upstream raw materials:

phenylcarbonochloridothioate

(1S,3S,8S,9R,13R)-9-hydroxy-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadec-10-ene

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

(1S,3S,8S,13R)-2,7,14-trioxatricyclo[11.4.0.0^3,8]heptadec-10-en-9-one

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