<3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester

Base Information

• Chemical Name: <3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester
• CAS No.: 115183-67-0
• Molecular Formula: C₄₀H₆₂O₇Si₂
• Molecular Weight: 711.099
• Mol file: 115183-67-0.mol

Synonyms:

Chemical Property of <3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester

There total 16 articles about <3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester 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:

(2S,3S)-2-(2-Hydroxy-ethyl)-3,6-dihydro-2H-pyran-3-ol → <3aS-<3aα,4α,7aα,7α(3E,2S*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester (115183-67-0)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / 2 h / 0 - 20 °C

2: 100 percent / xylene / 12 h / Heating

3: 90 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 24 h / Ambient temperature

4: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature

5: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C

6: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH₂Cl₂, -100 deg C, 1 h

7: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH₂Cl₂ / Ambient temperature

8: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C

9: diethyl ether / 0 °C

With pyridine; dmap; osmium(VIII) oxide; chloro-trimethyl-silane; diisobutylaluminium hydride; toluene-4-sulfonic acid; copper(II) sulfate; magnesium; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetone; xylene;

DOI:10.1021/jo00253a021

Reference yield:

2-{(3S,4R,5R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide (115118-80-4) → <3aS-<3aα,4α,7aα,7α(3E,2S*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester (115183-67-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature

2: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C

3: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH₂Cl₂, -100 deg C, 1 h

4: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH₂Cl₂ / Ambient temperature

5: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C

6: diethyl ether / 0 °C

With pyridine; dmap; chloro-trimethyl-silane; diisobutylaluminium hydride; toluene-4-sulfonic acid; copper(II) sulfate; magnesium; dicyclohexyl-carbodiimide; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo00253a021

Reference yield:

<3aR-(3aα,4α,7α,7aα)>-tetrahydro-N,N,2,2-tetramethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetamide (107148-24-3) → <3aS-<3aα,4α,7aα,7α(3E,2S*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester (115183-67-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi, BF₃ / 1.) THF, hexane, ether, -78 deg C, 20 min, 2.) 30 min

2: 85 percent / (-)-alpine borane / tetrahydrofuran / 24 h / Ambient temperature

3: 92 percent / LiAlH₄, sodium methoxide / tetrahydrofuran / 4.5 h / Heating

4: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH₂Cl₂ / Ambient temperature

5: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C

6: diethyl ether / 0 °C

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; boron trifluoride; sodium methylate; R-B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo00253a021

upstream raw materials:

diazomethane

2-{(3S,4R,5R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide

<3aR-(3aα,4α,7α,7aα)>-tetrahydro-N,N,2,2-tetramethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetamide

3,5-hexadienoyl chloride