(R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-((S)-1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propan-1-ol

Base Information

• Chemical Name: (R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-((S)-1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propan-1-ol
• CAS No.: 834917-15-6
• Molecular Formula: C₄₃H₈₆O₈Si₃
• Molecular Weight: 815.408

Synonyms:(R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-((S)-1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propan-1-ol

Chemical Property of (R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-((S)-1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-((S)-1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propan-1-ol

There total 19 articles about (R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-((S)-1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propan-1-ol 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:

2,2-dimethyl-propionic acid 2-{6-[6-(2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-(1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propyl ester → (R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-((S)-1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propan-1-ol (834917-15-6) + (R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-((R)-1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propan-1-ol (834916-96-0)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃;

DOI:10.1002/anie.200461802

Reference yield:

(1R,2S)-1-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-2-[(S)-hydroxy-((2R,4S,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-methyl]-4-methoxymethoxymethyl-cyclohex-3-enecarbonitrile (834916-83-5) → (R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-((S)-1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propan-1-ol (834917-15-6)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 88 percent / CSA / CH₂Cl₂ / 20 °C

2.1: DIBAL-H / toluene / -30 - 20 °C

2.2: SiO₂ / hexane / 20 °C

2.3: DIBAL-H / toluene / -78 - 0 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

4.1: 91 percent / Na; liq. NH₃ / tetrahydrofuran / -78 °C

5.1: pyridine / 20 °C

6.1: imidazole / dimethylformamide / 20 °C

7.1: DIBAL-H / toluene / -78 °C

8.1: SO₃*py; Et₃N; DMSO / CH₂Cl₂ / 20 °C

9.1: tetrahydrofuran / 0 °C

10.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

11.1: 95 percent / tetrahydrofuran / 20 °C

12.1: tetrahydrofuran / 20 °C

13.1: aq. H₂O₂; NaOH / 0 - 20 °C

14.1: DMAP; pyridine / 20 °C

15.1: TBAF / tetrahydrofuran / 20 °C

16.1: 84 percent / pyridinium dichromate / CH₂Cl₂ / 20 °C

17.1: 94 percent / imidazole / dimethylformamide / 20 °C

18.1: tetrahydrofuran / 0 °C

18.2: PivCl; DMAP; pyridine / 20 °C

18.3: imidazole / dimethylformamide / 20 °C

19.1: DIBAL-H / toluene / -78 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium hydroxide; dipyridinium dichromate; pyridine-SO₃ complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; sodium; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 10.1: Dess-Martin oxidation;

DOI:10.1002/anie.200461802

Reference yield:

[(1R,2S)-2-((4S,4aS,6R,8aR)-2,2-Dimethyl-6-phenyl-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-1-((2S,3R)-2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-4-methoxymethoxymethyl-cyclohex-3-enyl]-methanol → (R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-6-((S)-1-trimethylsilanyloxy-but-3-enyl)-cyclohex-2-enyl]-2,2-dimethyl-5-trimethylsilanyloxy-[1,3]dioxan-4-yl}-propan-1-ol (834917-15-6)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2.1: 91 percent / Na; liq. NH₃ / tetrahydrofuran / -78 °C

3.1: pyridine / 20 °C

4.1: imidazole / dimethylformamide / 20 °C

5.1: DIBAL-H / toluene / -78 °C

6.1: SO₃*py; Et₃N; DMSO / CH₂Cl₂ / 20 °C

7.1: tetrahydrofuran / 0 °C

8.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

9.1: 95 percent / tetrahydrofuran / 20 °C

10.1: tetrahydrofuran / 20 °C

11.1: aq. H₂O₂; NaOH / 0 - 20 °C

12.1: DMAP; pyridine / 20 °C

13.1: TBAF / tetrahydrofuran / 20 °C

14.1: 84 percent / pyridinium dichromate / CH₂Cl₂ / 20 °C

15.1: 94 percent / imidazole / dimethylformamide / 20 °C

16.1: tetrahydrofuran / 0 °C

16.2: PivCl; DMAP; pyridine / 20 °C

16.3: imidazole / dimethylformamide / 20 °C

17.1: DIBAL-H / toluene / -78 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium hydroxide; dipyridinium dichromate; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; sodium; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 8.1: Dess-Martin oxidation;

DOI:10.1002/anie.200461802

upstream raw materials:

(1R,2S)-1-((2S,3R)-2,3-Dimethyl-4-triisopropylsilanyloxy-butyl)-2-[(S)-hydroxy-((2R,4S,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-methyl]-4-methoxymethoxymethyl-cyclohex-3-enecarbonitrile

(1R,2S)-2-((4S,4aS,6R,8aR)-2,2-Dimethyl-6-phenyl-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl)-1-((2S,3R)-2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-4-methoxymethoxymethyl-cyclohex-3-enecarbonitrile

2,2-Dimethyl-propionic acid (R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-6-formyl-3-methoxymethoxymethyl-cyclohex-2-enyl]-5-hydroxy-2,2-dimethyl-[1,3]dioxan-4-yl}-propyl ester

2,2-Dimethyl-propionic acid (R)-2-{(4R,5S,6S)-6-[(1S,6R)-6-((2S,3R)-2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-6-hydroxymethyl-3-methoxymethoxymethyl-cyclohex-2-enyl]-5-hydroxy-2,2-dimethyl-[1,3]dioxan-4-yl}-propyl ester

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