(4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(hydroxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate

Base Information

• Chemical Name: (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(hydroxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate
• CAS No.: 930795-41-8
• Molecular Formula: C₄₁H₇₁NO₇Si
• Molecular Weight: 718.103

Synonyms:(4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(hydroxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate

Chemical Property of (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(hydroxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate

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Technology Process of (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(hydroxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate

There total 48 articles about (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(hydroxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl 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: 83.0%

(4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate (930795-40-7) → (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(hydroxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate (930795-41-8)

Guidance literature:

In tetrahydrofuran; water; at 0 ℃; for 7h;

DOI:10.1021/jo062396o

Reference yield:

(2S,4R,5R)-5-(tert-butyldimethylsilanyloxymethyl)-4-methyltetrahydrofuran-2-carbaldehyde (930795-06-5) → (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(hydroxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate (930795-41-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 - 20 °C

1.2: 82 percent / tetrahydrofuran; hexane / 1 h / 20 °C

2.1: H₂ / Pd/C / ethanol / 12 h / 20 °C

3.1: 12 mg / TBAF / tetrahydrofuran / 3 h / 20 °C

4.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.17 h / -78 - 0 °C

5.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h / -78 °C

5.2: 4.1 mg / tetrahydrofuran / -78 - 20 °C

6.1: LiAlH₄ / diethyl ether / 1 h / cooling

7.1: 37.2 mg / imidazole; DMAP / CH₂Cl₂ / 20 °C

8.1: n-Bu₃SnCu(CN)Li / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: DMPU / tetrahydrofuran; hexane / -78 - 20 °C

8.3: 89 percent / iodine / diethyl ether / 0.5 h / 20 °C

9.1: H₂O / tetrahydrofuran / 1 h / 20 °C

9.2: 28.1 mg / Cs₂CO₃; AsPh₃ / PdCl₂(dppf) / dimethylformamide; H₂O; tetrahydrofuran / 10 h / 20 °C

10.1: 83 percent / H₂O; tetrahydrofuran / 7 h / 0 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; n-Bu₃SnCu(CN)Li; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; 4.1: Swern oxidation / 9.2: Suzuki-Miyaura coupling;

DOI:10.1021/jo062396o

Reference yield:

(2S,4R,5R)-[5-(tert-butyldimethylsilanyloxymethyl)-4-methyltetrahydrofuran-2-yl]methanol (930795-05-4) → (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(hydroxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate (930795-41-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 - 20 °C

2.2: 82 percent / tetrahydrofuran; hexane / 1 h / 20 °C

3.1: H₂ / Pd/C / ethanol / 12 h / 20 °C

4.1: 12 mg / TBAF / tetrahydrofuran / 3 h / 20 °C

5.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.17 h / -78 - 0 °C

6.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h / -78 °C

6.2: 4.1 mg / tetrahydrofuran / -78 - 20 °C

7.1: LiAlH₄ / diethyl ether / 1 h / cooling

8.1: 37.2 mg / imidazole; DMAP / CH₂Cl₂ / 20 °C

9.1: n-Bu₃SnCu(CN)Li / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: DMPU / tetrahydrofuran; hexane / -78 - 20 °C

9.3: 89 percent / iodine / diethyl ether / 0.5 h / 20 °C

10.1: H₂O / tetrahydrofuran / 1 h / 20 °C

10.2: 28.1 mg / Cs₂CO₃; AsPh₃ / PdCl₂(dppf) / dimethylformamide; H₂O; tetrahydrofuran / 10 h / 20 °C

11.1: 83 percent / H₂O; tetrahydrofuran / 7 h / 0 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; n-Bu₃SnCu(CN)Li; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; 1.1: Swern oxidation / 5.1: Swern oxidation / 10.2: Suzuki-Miyaura coupling;

DOI:10.1021/jo062396o

upstream raw materials:

(4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate

(2S,4R,5R)-5-(tert-butyldimethylsilanyloxymethyl)-4-methyltetrahydrofuran-2-carbaldehyde

(2'R,4'R,5'R)-3-[5'-ethynyl-4'-methyltetrahydrofuran-2'-yl]propionic acid ethyl ester

(2'R,4'R,5'R)-3-[5'-hydroxymethyl-4'-methyltetrahydrofuran-2'-yl]propionic acid ethyl ester

Downstream raw materials:

(4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-ethynyl-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate

acetic acid 1-[1-(2-cyano-ethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-3-methyl-cyclohex-3-enyl]-5-[3-methyl-5-(3-triisopropylsilanyloxy-propyl)-tetrahydro-furan-2-yl]-hex-4-enyl ester

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