SESQUICILLIN

Base Information

• Chemical Name: SESQUICILLIN
• CAS No.: 51103-58-3
• Molecular Formula: C₂₉H₄₂O₅
• Molecular Weight: 470.649
• Hs Code.: 2941100000
• Mol file: 51103-58-3.mol

Synonyms:2H-Pyran-2-one,3-[[(1R,4aR,5S,6S,8aR)-6-(acetyloxy)decahydro-5,8a-dimethyl-2-methylene-5-(4-methyl-3-pentenyl)-1-naphthalenyl]methyl]-4-hydroxy-5,6-dimethyl-,rel-(-)- (9CI); 2H-Pyran-2-one,3-[[6-(acetyloxy)decahydro-5,8a-dimethyl-2-methylene-5-(4-methyl-3-pentenyl)-1-naphthalenyl]methyl]-4-hydroxy-5,6-dimethyl-,(1a,4aa,5a,6b,8ab)-(-)-; (-)-Sesquicillin; Sesquicillin; Sesquicillin A

Chemical Property of SESQUICILLIN

Chemical Property:

• PSA: 76.74000
• LogP: 6.57160

Purity/Quality:

99% ^*data from raw suppliers

Sesquicillin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of SESQUICILLIN

There total 27 articles about SESQUICILLIN 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: 88.0%

3-[(1R,4aR,5S,6S,8aR)-6-acetoxy-5,8a-dimethyl-2-methylene-5-(4-methylpent-3-enyl)decahydronaphthalen-1-yl]methyl-4-acetoxy-5,6-dimethyl-2H-pyran-2-one → sesquicillin (51103-58-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 0.5h;

DOI:10.3987/COM-08-S(S)2

Reference yield: 61.0%

2-[(1S,4aS,5S,6R,8aS)-6-Acetoxy-5,8a-dimethyl-2-methylene-5-(4-methyl-pent-3-enyl)-decahydro-naphthalen-1-ylmethyl]-4-methyl-3,5-dioxo-hexanoic acid methyl ester → DL-sesquicillin (51103-58-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; Heating;

DOI:10.1002/1521-3773(20020415)41:8<1434::AID-ANIE1434>3.0.CO;2-A

Reference yield:

5,5-ethylenedioxy-1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2[3H]-naphthalenone (31062-32-5) → DL-sesquicillin (51103-58-3)

Guidance literature:

Multi-step reaction with 25 steps

1.1: Li; ammonia; T-BuOH / tetrahydrofuran / -78 - 20 °C

1.2: 78 percent / tetrahydrofuran

2.1: NaBH₄ / ethanol

3.1: 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

4.1: BH₃*THF / 20 °C

4.2: NaOH; H₂O₂ / Heating

5.1: pyridinium chlorochromate / CH₂Cl₂

6.1: 85 percent / n-BuLi / dimethylsulfoxide

7.1: 98 percent / pyridinium p-toluenesulfonate / acetone / Heating

8.1: NaH / tetrahydrofuran / Heating

9.1: H₃PO₄

10.1: NaBH₄ / ethanol

11.1: HCl / tetrahydrofuran; H₂O

12.1: 100 percent / NaBH₄ / ethanol

13.1: 87 percent / xylene / Heating

14.1: 99 percent / superhydride / tetrahydrofuran

15.1: triethylamine / CH₂Cl₂

16.1: dimethylformamide

17.1: diisobutylaluminium hydride / hexane / -78 - 20 °C

18.1: NaClO₂; NaH₂PO₄; t-BuOH / H₂O

19.1: methanol; benzene

20.1: 62 percent / lithium diisopropylamide / tetrahydrofuran / -78 °C

21.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂

22.1: HF / acetonitrile

23.1: triethylamine; 4-(dimethylamino)pyridine / 2-methyl-propan-2-ol

24.1: 97 percent / [Pf(CH₃CN)2Cl₂] / acetone

25.1: 61 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / Heating

With 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; borane-THF; phosphoric acid; hydrogen fluoride; ammonia; pyridinium p-toluenesulfonate; lithium; sodium hydride; diisobutylaluminium hydride; lithium triethylborohydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; tert-butyl alcohol; lithium diisopropyl amide; [Pf(CH₃CN)2Cl₂]; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile; xylene; tert-butyl alcohol; benzene;

DOI:10.1002/1521-3773(20020415)41:8<1434::AID-ANIE1434>3.0.CO;2-A

upstream raw materials:

((1S,2S,4aR,5R,8aR)-5-((4-(methoxymethoxy)-5,6-dimethyl-2-oxo-2H-pyran-3-yl)methyl)-1,4a-dimethyl-6-methylene-1-(4-methylpent-3-enyl)decahydronaphthalen-2-yl) acetate

5,5-ethylenedioxy-1,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2[3H]-naphthalenone

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