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

Base Information

Chemical Name: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
CAS No.:287400-52-6
Molecular Formula:C₃₇H₅₄O₈Si
Molecular Weight:654.916
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 4 articles about 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 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: 73.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 287400-51-5
3,4-di-O-[2-[(1S)-1-phenylethoxy]acetyl]-6-O-triisopropylsilyl-2-C-methyl-D-glucal

: (R)-{(2R,5S,6R)-3-Methyl-5-[2-((S)-1-phenyl-ethoxy)-acetoxy]-6-triisopropylsilanyloxymethyl-5,6-dihydro-2H-pyran-2-yl}-((S)-1-phenyl-ethoxy)-acetic acid methyl ester

: 287400-52-6
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

Guidance literature:: 3,4-di-O-[2-[(1S)-1-phenylethoxy]acetyl]-6-O-triisopropylsilyl-2-C-methyl-D-glucal; With chloro-trimethyl-silane; lithium hexamethyldisilazane; In pyridine; at -78 ℃;

In pyridine; at -78 - 20 ℃; for 0.0416667h;

diazomethane;
DOI:10.1021/jo0002801

Reference yield:

: 13154-24-0
triisopropylsilyl chloride

: 287400-52-6
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

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; dmap; chloro-trimethyl-silane; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Condensation / 3.1: silylation / 3.2: Rearrangement / 3.3: Methylation;
DOI:10.1021/jo0002801

Reference yield:

: 287400-50-4
6-O-triisopropylsilyl-2-C-methyl-D-glucal

: 287400-52-6
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

Guidance literature:: Multi-step reaction with 2 steps

1.1: 88 percent / DCC; DMAP / CH₂Cl₂ / 1.5 h

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

2.2: 73 percent / pyridine; tetrahydrofuran; ethyl acetate / 0.23 h / -78 - 20 °C

With dmap; chloro-trimethyl-silane; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; 1.1: Condensation / 2.1: silylation / 2.2: Rearrangement / 2.3: Methylation;
DOI:10.1021/jo0002801