(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

Base Information

• Chemical Name: (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
• CAS No.: 287400-58-2
• Molecular Formula: C₄₃H₇₄O₈Si₂
• Molecular Weight: 775.227

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 12 articles about (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 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: 63.0%

(2R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-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]ethane → (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 (287400-58-2)

Guidance literature:

With sulfuric acid; In tetrahydrofuran;

DOI:10.1021/jo0002801

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (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 (287400-58-2)

Guidance literature:

Multi-step reaction with 10 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

5.1: 90 percent / imidazole; NEt₃; DMAP / CH₂Cl₂ / 3.25 h

6.1: 74 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C

7.1: 78 percent / NaH / dimethylformamide; various solvent(s) / 1.25 h / cooling

8.1: 0.0963 g / 9-BBN / tetrahydrofuran / 3 h / 110 °C

9.1: 0.0931 g / 2,6-lutidine; NEt₃ / CH₂Cl₂ / 25 h / 20 °C

10.1: 63 percent / aq. H₂SO₄ / tetrahydrofuran

With 1H-imidazole; 2,6-dimethylpyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; chloro-trimethyl-silane; sulfuric acid; sodium; sodium hydride; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; ammonia; N,N-dimethyl-formamide; toluene; 1.1: silylation / 2.1: Condensation / 3.1: silylation / 3.2: Rearrangement / 3.3: Methylation / 4.1: Reduction / 5.1: silylation / 6.1: debenzylation / 7.1: Alkylation / 8.1: hydroboration / 9.1: silylation / 10.1: desilylation;

DOI:10.1021/jo0002801

Reference yield:

(2R,3S,4R)-2-Hydroxymethyl-5-methyl-3,4-dihydro-2H-pyran-3,4-diol → (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 (287400-58-2)

Guidance literature:

Multi-step reaction with 10 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

5.1: 90 percent / imidazole; NEt₃; DMAP / CH₂Cl₂ / 3.25 h

6.1: 74 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C

7.1: 78 percent / NaH / dimethylformamide; various solvent(s) / 1.25 h / cooling

8.1: 0.0963 g / 9-BBN / tetrahydrofuran / 3 h / 110 °C

9.1: 0.0931 g / 2,6-lutidine; NEt₃ / CH₂Cl₂ / 25 h / 20 °C

10.1: 63 percent / aq. H₂SO₄ / tetrahydrofuran

With 1H-imidazole; 2,6-dimethylpyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; chloro-trimethyl-silane; sulfuric acid; sodium; sodium hydride; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; ammonia; N,N-dimethyl-formamide; toluene; 1.1: silylation / 2.1: Condensation / 3.1: silylation / 3.2: Rearrangement / 3.3: Methylation / 4.1: Reduction / 5.1: silylation / 6.1: debenzylation / 7.1: Alkylation / 8.1: hydroboration / 9.1: silylation / 10.1: desilylation;

DOI:10.1021/jo0002801

upstream raw materials:

triisopropylsilyl chloride

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

(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

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

Downstream raw materials:

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

(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

(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

(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

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