(2R)-2-[(2R,5S,6R)-5,6-dihydro-5-hydroxy-3-methyl-6-[[(triisopropylsilyl)oxy]methyl]-2H-pyran-2-yl]-2-[(1S)-1-phenylethoxy]-ethanol

Base Information

• Chemical Name: (2R)-2-[(2R,5S,6R)-5,6-dihydro-5-hydroxy-3-methyl-6-[[(triisopropylsilyl)oxy]methyl]-2H-pyran-2-yl]-2-[(1S)-1-phenylethoxy]-ethanol
• CAS No.: 287400-53-7
• Molecular Formula: C₂₆H₄₄O₅Si
• Molecular Weight: 464.718

Synonyms:(2R)-2-[(2R,5S,6R)-5,6-dihydro-5-hydroxy-3-methyl-6-[[(triisopropylsilyl)oxy]methyl]-2H-pyran-2-yl]-2-[(1S)-1-phenylethoxy]-ethanol

Chemical Property of (2R)-2-[(2R,5S,6R)-5,6-dihydro-5-hydroxy-3-methyl-6-[[(triisopropylsilyl)oxy]methyl]-2H-pyran-2-yl]-2-[(1S)-1-phenylethoxy]-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2R)-2-[(2R,5S,6R)-5,6-dihydro-5-hydroxy-3-methyl-6-[[(triisopropylsilyl)oxy]methyl]-2H-pyran-2-yl]-2-[(1S)-1-phenylethoxy]-ethanol

There total 6 articles about (2R)-2-[(2R,5S,6R)-5,6-dihydro-5-hydroxy-3-methyl-6-[[(triisopropylsilyl)oxy]methyl]-2H-pyran-2-yl]-2-[(1S)-1-phenylethoxy]-ethanol 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%

methyl (2S)-2-[(2R,5S,6R)-5,6-dihydro-3-methyl-5-[2-[(1S)-1-phenylethoxy]-acetyl]-6-[[(triisopropylsilyl)oxy]methyl]-2H-pyran-2-yl]-2-[(1S)-1-phenylethoxy]acetate (287400-52-6) → (2R)-2-[(2R,5S,6R)-5,6-dihydro-5-hydroxy-3-methyl-6-[[(triisopropylsilyl)oxy]methyl]-2H-pyran-2-yl]-2-[(1S)-1-phenylethoxy]-ethanol (287400-53-7)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -45 ℃; for 1.5h;

DOI:10.1021/jo0002801

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (2R)-2-[(2R,5S,6R)-5,6-dihydro-5-hydroxy-3-methyl-6-[[(triisopropylsilyl)oxy]methyl]-2H-pyran-2-yl]-2-[(1S)-1-phenylethoxy]-ethanol (287400-53-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1.5815 g / imidazole / dimethylformamide / 0.33 h

2.1: 88 percent / DCC; DMAP / CH₂Cl₂ / 1.5 h

3.1: LiHMDS; Me₃SiCl / pyridine; tetrahydrofuran / 0.6 h / -78 °C

3.2: 73 percent / pyridine; tetrahydrofuran; ethyl acetate / 0.23 h / -78 - 20 °C

4.1: 96 percent / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -45 °C

With 1H-imidazole; dmap; chloro-trimethyl-silane; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: silylation / 2.1: Condensation / 3.1: silylation / 3.2: Rearrangement / 3.3: Methylation / 4.1: Reduction;

DOI:10.1021/jo0002801

Reference yield:

(2R,3S,4R)-2-Hydroxymethyl-5-methyl-3,4-dihydro-2H-pyran-3,4-diol → (2R)-2-[(2R,5S,6R)-5,6-dihydro-5-hydroxy-3-methyl-6-[[(triisopropylsilyl)oxy]methyl]-2H-pyran-2-yl]-2-[(1S)-1-phenylethoxy]-ethanol (287400-53-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1.5815 g / imidazole / dimethylformamide / 0.33 h

2.1: 88 percent / DCC; DMAP / CH₂Cl₂ / 1.5 h

3.1: LiHMDS; Me₃SiCl / pyridine; tetrahydrofuran / 0.6 h / -78 °C

3.2: 73 percent / pyridine; tetrahydrofuran; ethyl acetate / 0.23 h / -78 - 20 °C

4.1: 96 percent / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -45 °C

With 1H-imidazole; dmap; chloro-trimethyl-silane; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: silylation / 2.1: Condensation / 3.1: silylation / 3.2: Rearrangement / 3.3: Methylation / 4.1: Reduction;

DOI:10.1021/jo0002801

upstream raw materials:

methyl (2S)-2-[(2R,5S,6R)-5,6-dihydro-3-methyl-5-[2-[(1S)-1-phenylethoxy]-acetyl]-6-[[(triisopropylsilyl)oxy]methyl]-2H-pyran-2-yl]-2-[(1S)-1-phenylethoxy]acetate

triisopropylsilyl chloride

6-O-triisopropylsilyl-2-C-methyl-D-glucal

3,4-di-O-[2-[(1S)-1-phenylethoxy]acetyl]-6-O-triisopropylsilyl-2-C-methyl-D-glucal

Downstream raw materials:

(1S,4R,5R,6R)-4-Hydroxy-1-(4-methoxy-benzyloxy)-1-[(2R,3S,4R,5R,6R)-5-(4-methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-5-methyl-6-triethylsilanyloxy-dec-9-en-2-one

(1S,4S,5R,6R)-4-Hydroxy-1-(4-methoxy-benzyloxy)-1-[(2R,3S,4R,5R,6R)-5-(4-methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-5-methyl-6-triethylsilanyloxy-dec-9-en-2-one

(2R,3S,4R,5R,6R)-2-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-allyl]-5-(4-methoxy-benzyloxy)-3-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran

(2R)-2-[(4-methoxyphenyl)methoxy]-2-[(2R,3S,4R,5S,6R)tetrahydro-5-[(4-methoxyphenyl)methoxy]-3-methyl-4-[(triisopropylsilyl)oxy]-6-[[(triisopropylsilyl)oxy]methyl]-2H-pyran-2-yl]-ethanol

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