(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

Base Information

• Chemical Name: (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
• CAS No.: 834916-83-5
• Molecular Formula: C₃₆H₅₉NO₇Si
• Molecular Weight: 645.952
• Mol file: 834916-83-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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: 72.0%

Methanesulfonic acid (E)-(1R,2S,9S,10R)-7-cyano-2-hydroxy-1-((2R,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-4-methoxymethoxymethyl-9,10-dimethyl-11-triisopropylsilanyloxy-undec-3-enyl ester (834916-82-4) → (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)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1002/anie.200461802

Reference yield: 88.0%

2,2-dimethoxy-propane (77-76-9) + (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) → (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 (834916-84-6)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃;

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) → {(4R,5S,6S)-6-[(1S,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-6-((2S,3R)-2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-cyclohex-2-enyl]-2,2-dimethyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl}-methanol (834916-87-9)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; camphor-10-sulfonic acid; ammonia; sodium; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/anie.200461802

upstream raw materials:

Methanesulfonic acid (E)-(1R,2S,9S,10R)-7-cyano-2-hydroxy-1-((2R,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-4-methoxymethoxymethyl-9,10-dimethyl-11-triisopropylsilanyloxy-undec-3-enyl ester

Downstream raw materials:

(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

(4S,5S,6R)-4-[(1S,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-6-((2S,3R)-2,3-dimethyl-4-triisopropylsilanyloxy-butyl)-3-methoxymethoxymethyl-cyclohex-2-enyl]-6-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-5-ol