(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-[(2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-methanol

Base Information

• Chemical Name: (S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-[(2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-methanol
• CAS No.: 779356-95-5
• Molecular Formula: C₅₁H₇₆O₈Si
• Molecular Weight: 845.245

Synonyms:(S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-[(2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-methanol

Chemical Property of (S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-[(2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-[(2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-methanol

There total 15 articles about (S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-[(2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-methanol 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%

methanol (67-56-1) + (2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-2-{(S)-[(2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-hydroxy-methyl}-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-ol (779356-94-4) → (S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-[(2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-methanol (779356-95-5)

Guidance literature:

With pyridinium p-toluenesulfonate; at 0 - 20 ℃; for 2h;

DOI:10.1021/ol048418f

Reference yield:

(Z)-4-heptenal (6728-31-0) → (S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-[(2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-methanol (779356-95-5)

Guidance literature:

Multi-step reaction with 14 steps

1.1: hexamethyldisilazane / CH₂Cl₂ / 18 h / 35 °C

1.2: 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / -78 °C

1.3: 86 percent / trifluoromethanesulfonic acid / CH₂Cl₂

2.1: ethyl trimethylacetate / tetrahydrofuran / 22 h / Heating

2.2: 100 percent / celite / tetrahydrofuran; hexane / 2 h / 20 °C

3.1: 77 percent / dimethylaluminum chloride; cesium carbonate / CH₂Cl₂ / 1.58 h / -78 - 20 °C

4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

4.2: 78 percent / (1S)-3,3-dimethoxy-(10-camphorsulfonyl)oxaziridine; hexamethylphosphoramide / tetrahydrofuran; CH₂Cl₂ / 2 h / -60 °C

5.1: 4.32 g / K₂CO₃ / methanol / 1 h

6.1: chlorotrimethylsilane; 4-dimethylaminopyridine; imidazole / CH₂Cl₂ / 24 h / 20 °C

6.2: 85 percent / tetrabutylammonium borohydride / CH₂Cl₂ / 3.5 h / -78 - -40 °C

7.1: 100 percent / sodium hydride / dimethylformamide; tetrahydrofuran / 6 h / 20 °C

8.1: 100 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.05 h / 20 °C

9.1: 99 percent / DMSO; SO₃*Py; N,N-diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 0.67 h / -78 - -50 °C

10.2: CeCl₃ / tetrahydrofuran; hexane / 1.5 h / -78 °C

10.3: 68 percent / ZnCl₂ / tetrahydrofuran; hexane; diethyl ether / 3 h / -78 °C

11.1: 95 percent / p-toluenesulfonic acid monohydrate / acetonitrile; tetrahydrofuran; H₂O / 2.5 h

12.1: 81 percent / 2,6-lutidine; CaCO₃; methyl iodide / acetonitrile; tetrahydrofuran; H₂O / 36 h

13.1: 84 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

14.1: 96 percent / pyridinium p-toluenesulfonate / 2 h / 0 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; chloro-trimethyl-silane; ammonium cerium(IV) nitrate; pyridine-SO₃ complex; 2,2-dimethyl-propanoic acid ethyl ester; dimethylaluminum chloride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; methyl iodide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 2.1: Petasis-Tebbe methylenation / 3.1: Petasis-Ferrier rearrangement / 9.1: Parikh-Doering oxidation;

DOI:10.1021/ol048418f

Reference yield:

(2R,3R)-3-Hydroxy-4-(4-methoxy-phenoxy)-2-methyl-butyric acid (779356-69-3) → (S)-[(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-[(2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-methanol (779356-95-5)

Guidance literature:

Multi-step reaction with 14 steps

1.1: hexamethyldisilazane / CH₂Cl₂ / 18 h / 35 °C

1.2: 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / -78 °C

1.3: 86 percent / trifluoromethanesulfonic acid / CH₂Cl₂

2.1: ethyl trimethylacetate / tetrahydrofuran / 22 h / Heating

2.2: 100 percent / celite / tetrahydrofuran; hexane / 2 h / 20 °C

3.1: 77 percent / dimethylaluminum chloride; cesium carbonate / CH₂Cl₂ / 1.58 h / -78 - 20 °C

4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

4.2: 78 percent / (1S)-3,3-dimethoxy-(10-camphorsulfonyl)oxaziridine; hexamethylphosphoramide / tetrahydrofuran; CH₂Cl₂ / 2 h / -60 °C

5.1: 4.32 g / K₂CO₃ / methanol / 1 h

6.1: chlorotrimethylsilane; 4-dimethylaminopyridine; imidazole / CH₂Cl₂ / 24 h / 20 °C

6.2: 85 percent / tetrabutylammonium borohydride / CH₂Cl₂ / 3.5 h / -78 - -40 °C

7.1: 100 percent / sodium hydride / dimethylformamide; tetrahydrofuran / 6 h / 20 °C

8.1: 100 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.05 h / 20 °C

9.1: 99 percent / DMSO; SO₃*Py; N,N-diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 0.67 h / -78 - -50 °C

10.2: CeCl₃ / tetrahydrofuran; hexane / 1.5 h / -78 °C

10.3: 68 percent / ZnCl₂ / tetrahydrofuran; hexane; diethyl ether / 3 h / -78 °C

11.1: 95 percent / p-toluenesulfonic acid monohydrate / acetonitrile; tetrahydrofuran; H₂O / 2.5 h

12.1: 81 percent / 2,6-lutidine; CaCO₃; methyl iodide / acetonitrile; tetrahydrofuran; H₂O / 36 h

13.1: 84 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

14.1: 96 percent / pyridinium p-toluenesulfonate / 2 h / 0 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; chloro-trimethyl-silane; ammonium cerium(IV) nitrate; pyridine-SO₃ complex; 2,2-dimethyl-propanoic acid ethyl ester; dimethylaluminum chloride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; methyl iodide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 2.1: Petasis-Tebbe methylenation / 3.1: Petasis-Ferrier rearrangement / 9.1: Parikh-Doering oxidation;

DOI:10.1021/ol048418f

upstream raw materials:

methanol

(2R,4S,5S,6R)-6-(4-Benzyloxy-butyl)-2-{(S)-[(2R,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-((Z)-hex-3-enyl)-3-methyl-tetrahydro-pyran-2-yl]-hydroxy-methyl}-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-ol

(Z)-4-heptenal

(2R,3R)-3-Hydroxy-4-(4-methoxy-phenoxy)-2-methyl-butyric acid

Downstream raw materials:

C₇₅H₁₂₉ClO₈PSi₅⁽¹⁺⁾*I^(1-)

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