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

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((S)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester
• CAS No.: 865446-74-8
• Molecular Formula: C₄₃H₅₆O₉S₂
• Molecular Weight: 781.044

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

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

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

There total 15 articles about Toluene-4-sulfonic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((S)-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: 59.0%

(2R,3S)-4-{(R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((S)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butan-1-ol (865446-73-7) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((S)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester (865446-74-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 50 ℃; for 24h;

DOI:10.1021/ol050321l

Reference yield:

2,2-Dimethyl-propionic acid (2R,3R)-4-hydroxy-2,3-dimethyl-butyl ester (851370-34-8) → Toluene-4-sulfonic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((S)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester (865446-74-8)

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: 84 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

9.1: 100 percent / DIBAL / CH₂Cl₂; toluene / 0.33 h / -78 °C

10.1: 59 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 50 °C

With pyridine; 1H-imidazole; dmap; chloro-trimethyl-silane; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; 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) → Toluene-4-sulfonic acid (2R,3S)-4-{(R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-[3-(4-methoxy-benzyloxy)-propyl]-6-[(E)-2-((S)-toluene-4-sulfinyl)-vinyl]-5,6-dihydro-4H-pyran-3-yl}-2,3-dimethyl-butyl ester (865446-74-8)

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: 84 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

8.1: 100 percent / DIBAL / CH₂Cl₂; toluene / 0.33 h / -78 °C

9.1: 59 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 50 °C

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

DOI:10.1021/ol050321l

upstream raw materials:

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

p-toluenesulfonyl chloride

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

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