2,2-Dimethyl-propionic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((R)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((R)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester
• CAS No.: 851370-39-3
• Molecular Formula: C₄₁H₅₈O₈S
• Molecular Weight: 710.973

Synonyms:2,2-Dimethyl-propionic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((R)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((R)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((R)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester

There total 13 articles about 2,2-Dimethyl-propionic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((R)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester 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 (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-[1-hydroxy-2-((R)-toluene-4-sulfinyl)-ethyl]-2-[3-(4-methoxy-benzyloxy)-propyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester → 2,2-Dimethyl-propionic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((R)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester (851370-39-3)

Guidance literature:

2,2-Dimethyl-propionic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-[1-hydroxy-2-((R)-toluene-4-sulfinyl)-ethyl]-2-[3-(4-methoxy-benzyloxy)-propyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester; With chloro-trimethyl-silane; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 15h;

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/ol050321l

Reference yield:

2,2-Dimethyl-propionic acid (2R,3R)-4-hydroxy-2,3-dimethyl-butyl ester (851370-34-8) → 2,2-Dimethyl-propionic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((R)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester (851370-39-3)

Guidance literature:

Multi-step reaction with 8 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

With 1H-imidazole; chloro-trimethyl-silane; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; pentane; 4.3: Negishi coupling;

DOI:10.1021/ol050321l

Reference yield:

2,2-Dimethyl-propionic acid (2R,3R)-4-iodo-2,3-dimethyl-butyl ester (851370-21-3) → 2,2-Dimethyl-propionic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((R)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester (851370-39-3)

Guidance literature:

Multi-step reaction with 7 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

With chloro-trimethyl-silane; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; pentane; 3.3: Negishi coupling;

DOI:10.1021/ol050321l

upstream raw materials:

2,2-Dimethyl-propionic acid (2R,3R)-4-hydroxy-2,3-dimethyl-butyl ester

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

(R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-one

2,2-Dimethyl-propionic acid (2R,3S)-4-[(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-6-triisopropylsilanyloxymethyl-5,6-dihydro-4H-pyran-3-yl]-2,3-dimethyl-butyl ester

Downstream raw materials:

Acetic acid (1R,4R)-4-((2S,3R)-4-azido-2,3-dimethyl-butyl)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-[4-(4-methoxy-benzyloxy)-butyryl]-cyclohex-2-enyl ester

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

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

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

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