(S)-6-[(1S,3S)-2,2-Bis-benzenesulfonyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-tetrahydro-pyran-2-one

Base Information

• Chemical Name: (S)-6-[(1S,3S)-2,2-Bis-benzenesulfonyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-tetrahydro-pyran-2-one
• CAS No.: 452920-25-1
• Molecular Formula: C₂₅H₂₈O₈S₂
• Molecular Weight: 520.625

Synonyms:(S)-6-[(1S,3S)-2,2-Bis-benzenesulfonyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-tetrahydro-pyran-2-one

Chemical Property of (S)-6-[(1S,3S)-2,2-Bis-benzenesulfonyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-tetrahydro-pyran-2-one

Chemical Property:

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Technology Process of (S)-6-[(1S,3S)-2,2-Bis-benzenesulfonyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-tetrahydro-pyran-2-one

There total 10 articles about (S)-6-[(1S,3S)-2,2-Bis-benzenesulfonyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-tetrahydro-pyran-2-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: 80.0%

(E)-(S)-8,8-Bis-benzenesulfonyl-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-oct-5-enoic acid (452920-24-0) → (S)-6-[(1S,3S)-2,2-Bis-benzenesulfonyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-tetrahydro-pyran-2-one (452920-25-1)

Guidance literature:

With iodine; sodium hydride; In tetrahydrofuran; at 68 ℃; for 44h;

DOI:10.1016/S0040-4039(02)00699-8

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (S)-6-[(1S,3S)-2,2-Bis-benzenesulfonyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-tetrahydro-pyran-2-one (452920-25-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

1.2: tetrahydrofuran / 5 h / -78 - 20 °C

2.1: 88 percent / PPh₃; DEAD / benzene / 12 h / 23 °C

3.1: 92 percent / NaOH / methanol / 12 h / 23 °C

4.1: PPh₃; DEAD / benzene / 3 h / 23 °C

5.1: CrSO₄; H₂O / dimethylformamide / 2 h / 23 °C

6.1: n-Bu₄NF / tetrahydrofuran / 18 h / 23 °C

7.1: PDC / dimethylformamide / 40 h / 23 °C

8.1: NaH; I₂ / tetrahydrofuran

With sodium hydroxide; dipyridinium dichromate; n-butyllithium; chromium sulfate; tetrabutyl ammonium fluoride; water; iodine; sodium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; benzene; 2.1: Mitsunobu inversion;

DOI:10.1016/S0040-4039(02)00699-8

Reference yield:

6-(tert-butyldiphenylsilyloxy)hexyne lithium → (S)-6-[(1S,3S)-2,2-Bis-benzenesulfonyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-tetrahydro-pyran-2-one (452920-25-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

1.2: tetrahydrofuran / 5 h / -78 - 20 °C

2.1: 88 percent / PPh₃; DEAD / benzene / 12 h / 23 °C

3.1: 92 percent / NaOH / methanol / 12 h / 23 °C

4.1: PPh₃; DEAD / benzene / 3 h / 23 °C

5.1: CrSO₄; H₂O / dimethylformamide / 2 h / 23 °C

6.1: n-Bu₄NF / tetrahydrofuran / 18 h / 23 °C

7.1: PDC / dimethylformamide / 40 h / 23 °C

8.1: NaH; I₂ / tetrahydrofuran

With sodium hydroxide; dipyridinium dichromate; n-butyllithium; chromium sulfate; tetrabutyl ammonium fluoride; water; iodine; sodium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; benzene; 2.1: Mitsunobu inversion;

DOI:10.1016/S0040-4039(02)00699-8

upstream raw materials:

(E)-(S)-8,8-Bis-benzenesulfonyl-7-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-oct-5-enoic acid

bis(phenylsulfonyl)methane

2,3-isopropylidene-glyceraldehyde

(S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-2-yn-1-ol

Downstream raw materials:

(R)-6-{(1S,2S)-2-[(2E,6Z)-(1R,4S)-1-Hydroxy-4-(4-methoxy-benzyloxy)-dodeca-2,6-dienyl]-cyclopropyl}-tetrahydro-pyran-2-one

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