[(2S),(2S,6S,7E,10S,11S,12E),(2R,6R)]-tert-butyl-(2-{6-[10-(4-methoxybenzyloxy)-6,11-bismethoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylenetrideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)-dimethylsilane

Base Information

• Chemical Name: [(2S),(2S,6S,7E,10S,11S,12E),(2R,6R)]-tert-butyl-(2-{6-[10-(4-methoxybenzyloxy)-6,11-bismethoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylenetrideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)-dimethylsilane
• CAS No.: 385809-24-5
• Molecular Formula: C₄₆H₇₄O₉Si
• Molecular Weight: 799.174

Synonyms:[(2S),(2S,6S,7E,10S,11S,12E),(2R,6R)]-tert-butyl-(2-{6-[10-(4-methoxybenzyloxy)-6,11-bismethoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylenetrideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)-dimethylsilane

Chemical Property of [(2S),(2S,6S,7E,10S,11S,12E),(2R,6R)]-tert-butyl-(2-{6-[10-(4-methoxybenzyloxy)-6,11-bismethoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylenetrideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)-dimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S),(2S,6S,7E,10S,11S,12E),(2R,6R)]-tert-butyl-(2-{6-[10-(4-methoxybenzyloxy)-6,11-bismethoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylenetrideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)-dimethylsilane

There total 57 articles about [(2S),(2S,6S,7E,10S,11S,12E),(2R,6R)]-tert-butyl-(2-{6-[10-(4-methoxybenzyloxy)-6,11-bismethoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylenetrideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)-dimethylsilane 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: 57.0%

[(2R,6R),(2S),2S]-4-(3-{6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methylpropyl)-2-methoxymethoxypent-4-enal (312695-75-3) + [(2S),3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enyl-1-sulfonyl}-1-phenyl-1H-tetrazol (385809-23-4) → [(2S),(2S,6S,7Z,10S,11S,12E),(2R,6R)]-tert-butyl-(2-{6-[10-(4-methoxybenzyloxy)-6,11-bismethoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylenetrideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)-dimethylsilane + [(2S),(2S,6S,7E,10S,11S,12E),(2R,6R)]-tert-butyl-(2-{6-[10-(4-methoxybenzyloxy)-6,11-bismethoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylenetrideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)-dimethylsilane (385809-24-5)

Guidance literature:

[(2S),3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enyl-1-sulfonyl}-1-phenyl-1H-tetrazol; With potassium hexamethylsilazane; In 1,2-dimethoxyethane; at -60 ℃; for 0.416667h;

[(2R,6R),(2S),2S]-4-(3-{6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methylpropyl)-2-methoxymethoxypent-4-enal; In 1,2-dimethoxyethane; at -60 - 20 ℃; for 4h;

DOI:10.1002/1521-3773(20011015)40:20<3842::AID-ANIE3842>3.0.CO;2-R

Reference yield:

(S)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one (89408-85-5) → [(2S),(2S,6S,7E,10S,11S,12E),(2R,6R)]-tert-butyl-(2-{6-[10-(4-methoxybenzyloxy)-6,11-bismethoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylenetrideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)-dimethylsilane (385809-24-5)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 89 percent / imidazole; DMAP / CH₂Cl₂; toluene / 16 h / 0 - 20 °C

2.1: CuI / 0 °C

2.2: 84 percent / diethyl ether / 1 h / 0 °C

3.1: 98 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

4.1: 83 percent / Bu₃P / tetrahydrofuran / 16 h / 0 - 20 °C

5.1: Et₃N / CH₂Cl₂ / 1 h / -10 °C

6.1: TBAF / tetrahydrofuran / 1 h / 0 - 5 °C

6.2: 812 mg / aq. NaOH / tetrahydrofuran / 0.75 h / 0 - 5 °C

7.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 1.5 h / -78 °C

7.2: aq. TFA / 3 h / 20 °C

7.3: 88 percent / DBU / CH₂Cl₂ / 0.5 h / 0 - 5 °C

8.1: 100 percent / magnesium monoperoxophthalate hexahydrate / ethanol / 1.5 h / 20 °C

9.1: DIBALH / CH₂Cl₂ / 1 h / -78 °C

10.1: 1.107 g / PPTS / 20 °C

11.1: montmorillonite K₁₀ clay / CH₂Cl₂ / 0.67 h / 0 - 5 °C

11.2: montmorillonite K₁₀ clay / CH₂Cl₂; H₂O / 0.5 h / 20 °C

11.3: 86 percent / NaBH₄ / methanol / 0.33 h / 0 - 5 °C

12.1: 98 percent / imidazole DMAP / CH₂Cl₂; toluene / 16 h / 20 °C

13.1: n-BuLi / tetrahydrofuran; hexane / 0.42 h / -78 °C

13.2: 86 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 2.5 h / -78 °C

14.1: 94 percent / iPr₂NEt / CH₂Cl₂ / 18 h / 20 °C

15.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.5 h / -78 °C

15.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 - -25 °C

16.1: 89 percent / DDQ / CH₂Cl₂ / 2.5 h / 20 °C / pH 7

17.1: 93 percent / (COCl)2; DMSO; iPr₂NEt / CH₂Cl₂ / -78 - 20 °C

18.1: KHDMS / 1,2-dimethoxy-ethane; toluene / 0.67 h / -60 °C

18.2: 57 percent / 1,2-dimethoxy-ethane; toluene / 4 h / -55 - 20 °C

With 1H-imidazole; dmap; copper(l) iodide; lithium borohydride; n-butyllithium; oxalyl dichloride; magnesium bis(monoperoxyphthalate)hexahydrate; tributylphosphine; Montmorillonite K₁₀ clay; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; toluene; 17.1: Swern oxidation / 18.2: Julia-Kocienski olefination;

DOI:10.1021/jo026743f

Reference yield:

[4R,6S]-6-(tert-butyldimethylsilanyloxymethyl)-4-methyl-tetrahydropyran-2-one (385809-06-3) → [(2S),(2S,6S,7E,10S,11S,12E),(2R,6R)]-tert-butyl-(2-{6-[10-(4-methoxybenzyloxy)-6,11-bismethoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylenetrideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)-dimethylsilane (385809-24-5)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 98 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

2.1: 83 percent / Bu₃P / tetrahydrofuran / 16 h / 0 - 20 °C

3.1: Et₃N / CH₂Cl₂ / 1 h / -10 °C

4.1: TBAF / tetrahydrofuran / 1 h / 0 - 5 °C

4.2: 812 mg / aq. NaOH / tetrahydrofuran / 0.75 h / 0 - 5 °C

5.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 1.5 h / -78 °C

5.2: aq. TFA / 3 h / 20 °C

5.3: 88 percent / DBU / CH₂Cl₂ / 0.5 h / 0 - 5 °C

6.1: 100 percent / magnesium monoperoxophthalate hexahydrate / ethanol / 1.5 h / 20 °C

7.1: DIBALH / CH₂Cl₂ / 1 h / -78 °C

8.1: 1.107 g / PPTS / 20 °C

9.1: montmorillonite K₁₀ clay / CH₂Cl₂ / 0.67 h / 0 - 5 °C

9.2: montmorillonite K₁₀ clay / CH₂Cl₂; H₂O / 0.5 h / 20 °C

9.3: 86 percent / NaBH₄ / methanol / 0.33 h / 0 - 5 °C

10.1: 98 percent / imidazole DMAP / CH₂Cl₂; toluene / 16 h / 20 °C

11.1: n-BuLi / tetrahydrofuran; hexane / 0.42 h / -78 °C

11.2: 86 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 2.5 h / -78 °C

12.1: 94 percent / iPr₂NEt / CH₂Cl₂ / 18 h / 20 °C

13.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.5 h / -78 °C

13.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 - -25 °C

14.1: 89 percent / DDQ / CH₂Cl₂ / 2.5 h / 20 °C / pH 7

15.1: 93 percent / (COCl)2; DMSO; iPr₂NEt / CH₂Cl₂ / -78 - 20 °C

16.1: KHDMS / 1,2-dimethoxy-ethane; toluene / 0.67 h / -60 °C

16.2: 57 percent / 1,2-dimethoxy-ethane; toluene / 4 h / -55 - 20 °C

With 1H-imidazole; dmap; lithium borohydride; n-butyllithium; oxalyl dichloride; magnesium bis(monoperoxyphthalate)hexahydrate; tributylphosphine; Montmorillonite K₁₀ clay; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; toluene; 15.1: Swern oxidation / 16.2: Julia-Kocienski olefination;

DOI:10.1021/jo026743f

upstream raw materials:

[(2R,6R),(2S),2S]-4-(3-{6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methylpropyl)-2-methoxymethoxypent-4-enal

[(2S),3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enyl-1-sulfonyl}-1-phenyl-1H-tetrazol

(5S,6R)-5-acetoxy-6-(acetoxymethyl)-5,6-dihydro-2H-pyran-2-one

(2S)-acetic acid 6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester

Downstream raw materials:

laulimalide

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