(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

Base Information

Chemical Name:(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
CAS No.:287400-60-6
Molecular Formula:C₅₀H₈₈O₈Si₃
Molecular Weight:901.5
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 16 articles about (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 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: 97.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 287400-59-3
(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

: 287400-60-6
(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

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - 20 ℃; for 0.616667h;
DOI:10.1021/jo0002801

Reference yield:

: 13154-24-0
triisopropylsilyl chloride

: 287400-60-6
(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

Guidance literature:: Multi-step reaction with 14 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

11.1: Dess-Martin periodinane / CH₂Cl₂ / 0.58 h

12.1: 0.0349 g / tetrahydrofuran / 0.25 h / -78 °C

13.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

14.1: 97 percent / LiHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / 0.62 h / -78 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; chloro-trimethyl-silane; sulfuric acid; sodium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 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 / 11.1: Oxidation / 12.1: Addition / 13.1: Oxidation / 14.1: silylation;
DOI:10.1021/jo0002801

Reference yield:

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

: 287400-60-6
(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

Guidance literature:: Multi-step reaction with 14 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

11.1: Dess-Martin periodinane / CH₂Cl₂ / 0.58 h

12.1: 0.0349 g / tetrahydrofuran / 0.25 h / -78 °C

13.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

14.1: 97 percent / LiHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / 0.62 h / -78 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; chloro-trimethyl-silane; sulfuric acid; sodium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 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 / 11.1: Oxidation / 12.1: Addition / 13.1: Oxidation / 14.1: silylation;
DOI:10.1021/jo0002801