(3S,4S)-4-tert-butyldimethylsilyloxymethyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-trimethylsilyloxyhex-1-ene

Base Information

• Chemical Name: (3S,4S)-4-tert-butyldimethylsilyloxymethyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-trimethylsilyloxyhex-1-ene
• CAS No.: 1333325-51-1
• Molecular Formula: C₃₃H₅₆O₃Si₃
• Molecular Weight: 585.062

Synonyms:(3S,4S)-4-tert-butyldimethylsilyloxymethyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-trimethylsilyloxyhex-1-ene

Chemical Property of (3S,4S)-4-tert-butyldimethylsilyloxymethyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-trimethylsilyloxyhex-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (3S,4S)-4-tert-butyldimethylsilyloxymethyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-trimethylsilyloxyhex-1-ene

There total 21 articles about (3S,4S)-4-tert-butyldimethylsilyloxymethyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-trimethylsilyloxyhex-1-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:

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (3S,4S)-4-tert-butyldimethylsilyloxymethyl-6-tert-butyldiphenylsilyloxy-3-methylhexan-2-one (1333325-50-0) → (3S,4S)-4-tert-butyldimethylsilyloxymethyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-trimethylsilyloxyhex-1-ene (1333325-51-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/ol202265g

Reference yield:

(S)-4-oxo-4-((R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)-2-(2-oxoethyl)but-1-yl acetate (1333325-54-4) → (3S,4S)-4-tert-butyldimethylsilyloxymethyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-trimethylsilyloxyhex-1-ene (1333325-51-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

2.1: 1H-imidazole; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

3.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C

4.1: toluene-4-sulfonic acid / toluene / 2 h / 20 °C

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

5.2: 3 h / -78 °C / Inert atmosphere

6.1: tetrahydrofuran; diethyl ether / 3 h / -78 °C / Inert atmosphere

7.1: 1H-imidazole / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; dimethylsulfide borane complex; dihydrogen peroxide; sodium hexamethyldisilazane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol202265g

Reference yield:

(S)-2-(2-hydroxyethyl)-4-oxo-4-((R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-1-yl acetate (1333325-55-5) → (3S,4S)-4-tert-butyldimethylsilyloxymethyl-6-tert-butyldiphenylsilyloxy-3-methyl-2-trimethylsilyloxyhex-1-ene (1333325-51-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1H-imidazole; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C

3.1: toluene-4-sulfonic acid / toluene / 2 h / 20 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 3 h / -78 °C / Inert atmosphere

5.1: tetrahydrofuran; diethyl ether / 3 h / -78 °C / Inert atmosphere

6.1: 1H-imidazole / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; dihydrogen peroxide; sodium hexamethyldisilazane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol202265g

upstream raw materials:

(3S,4S)-dihydro-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3-methyl-2(3H)-furanone

(S)-2-(2-oxo-2-((R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)ethyl)pent-4-en-1-yl acetate

(S)-4-oxo-4-((R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)-2-(2-oxoethyl)but-1-yl acetate

(S)-2-(2-hydroxyethyl)-4-oxo-4-((R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-1-yl acetate

Downstream raw materials:

2-propenyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate

C₆₀H₇₀O₈Si

C₆₀H₇₀O₈Si

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