1-[(1R,4R)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-1-((2S,3R)-4-hydroxy-2,3-dimethyl-butyl)-cyclohex-2-enyl]-4-(4-methoxy-benzyloxy)-butan-1-one

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Chemical Name:1-[(1R,4R)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-1-((2S,3R)-4-hydroxy-2,3-dimethyl-butyl)-cyclohex-2-enyl]-4-(4-methoxy-benzyloxy)-butan-1-one
CAS No.:851370-40-6
Molecular Formula:C₂₉H₄₄O₇
Molecular Weight:504.664
Hs Code.:

Synonyms:1-[(1R,4R)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-1-((2S,3R)-4-hydroxy-2,3-dimethyl-butyl)-cyclohex-2-enyl]-4-(4-methoxy-benzyloxy)-butan-1-one

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Chemical Property of 1-[(1R,4R)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-1-((2S,3R)-4-hydroxy-2,3-dimethyl-butyl)-cyclohex-2-enyl]-4-(4-methoxy-benzyloxy)-butan-1-one

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Technology Process of 1-[(1R,4R)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-1-((2S,3R)-4-hydroxy-2,3-dimethyl-butyl)-cyclohex-2-enyl]-4-(4-methoxy-benzyloxy)-butan-1-one

There total 15 articles about 1-[(1R,4R)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-1-((2S,3R)-4-hydroxy-2,3-dimethyl-butyl)-cyclohex-2-enyl]-4-(4-methoxy-benzyloxy)-butan-1-one 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: 85.0%

: 851370-27-9
2,2-Dimethyl-propionic acid (2R,3S)-4-{(1R,4R)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-1-[4-(4-methoxy-benzyloxy)-butyryl]-cyclohex-2-enyl}-2,3-dimethyl-butyl ester

: 851370-40-6
1-[(1R,4R)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-1-((2S,3R)-4-hydroxy-2,3-dimethyl-butyl)-cyclohex-2-enyl]-4-(4-methoxy-benzyloxy)-butan-1-one

Guidance literature:: With sodium methylate; In methanol; at 50 ℃; for 15h;
DOI:10.1021/ol050321l

Reference yield:

: 851370-21-3
2,2-Dimethyl-propionic acid (2R,3R)-4-iodo-2,3-dimethyl-butyl ester

: 851370-40-6
1-[(1R,4R)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-1-((2S,3R)-4-hydroxy-2,3-dimethyl-butyl)-cyclohex-2-enyl]-4-(4-methoxy-benzyloxy)-butan-1-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: LDA / tetrahydrofuran / 0.33 h / -78 °C

1.2: 85 percent / DMPU / tetrahydrofuran / 3 h / 0 °C

2.1: 95 percent / KHMDS / tetrahydrofuran / -78 °C

3.1: t-BuLi / tetrahydrofuran; pentane / 0.17 h / -78 °C

3.2: ZnCl₂ / tetrahydrofuran; pentane / 0.08 h

3.3: 75 percent / NMP / Pd[P(t-Bu)3]2 / tetrahydrofuran; pentane / 0.5 h / -78 - 20 °C

4.1: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

5.1: SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 12 h / 20 °C

6.1: LDA / tetrahydrofuran / 0.33 h / 0 °C

6.2: tetrahydrofuran / 1 h / -78 °C

7.1: TMSCl; KHMDS / tetrahydrofuran; toluene / 15 h / -78 °C

7.2: LDA / tetrahydrofuran / 0.5 h / -78 °C

8.1: 88 percent / triethyl phosphite; s-collidine; MeOCH₂CH₂OCH₂CH₂OH / 15 h / 150 °C

9.1: 85 percent / MeONa / methanol / 15 h / 50 °C

With 2,4,6-trimethyl-pyridine; chloro-trimethyl-silane; pyridine-SO₃ complex; 2-(2-methoxyethoxy)ethanamine; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium methylate; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; triethyl phosphite; In tetrahydrofuran; methanol; dichloromethane; toluene; pentane; 3.3: Negishi coupling;
DOI:10.1021/ol050321l

Reference yield:

: 851370-34-8
2,2-Dimethyl-propionic acid (2R,3R)-4-hydroxy-2,3-dimethyl-butyl ester

: 851370-40-6
1-[(1R,4R)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-1-((2S,3R)-4-hydroxy-2,3-dimethyl-butyl)-cyclohex-2-enyl]-4-(4-methoxy-benzyloxy)-butan-1-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 95 percent / I₂; Ph₃P; imidazole / CH₂Cl₂ / 14 h / 20 °C

2.1: LDA / tetrahydrofuran / 0.33 h / -78 °C

2.2: 85 percent / DMPU / tetrahydrofuran / 3 h / 0 °C

3.1: 95 percent / KHMDS / tetrahydrofuran / -78 °C

4.1: t-BuLi / tetrahydrofuran; pentane / 0.17 h / -78 °C

4.2: ZnCl₂ / tetrahydrofuran; pentane / 0.08 h

4.3: 75 percent / NMP / Pd[P(t-Bu)3]2 / tetrahydrofuran; pentane / 0.5 h / -78 - 20 °C

5.1: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

6.1: SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 12 h / 20 °C

7.1: LDA / tetrahydrofuran / 0.33 h / 0 °C

7.2: tetrahydrofuran / 1 h / -78 °C

8.1: TMSCl; KHMDS / tetrahydrofuran; toluene / 15 h / -78 °C

8.2: LDA / tetrahydrofuran / 0.5 h / -78 °C

9.1: 88 percent / triethyl phosphite; s-collidine; MeOCH₂CH₂OCH₂CH₂OH / 15 h / 150 °C

10.1: 85 percent / MeONa / methanol / 15 h / 50 °C

With 1H-imidazole; 2,4,6-trimethyl-pyridine; chloro-trimethyl-silane; pyridine-SO₃ complex; 2-(2-methoxyethoxy)ethanamine; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; sodium methylate; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; triethyl phosphite; In tetrahydrofuran; methanol; dichloromethane; toluene; pentane; 4.3: Negishi coupling;
DOI:10.1021/ol050321l