(2RS)-2-thiophenoxy-2,35:12,13:12,13-hexahydrotrilobin-bis(methoxymethoxy) ether

Base Information

Chemical Name:(2RS)-2-thiophenoxy-2,35:12,13:12,13-hexahydrotrilobin-bis(methoxymethoxy) ether
CAS No.:224037-56-3
Molecular Formula:C₄₇H₇₆O₉S
Molecular Weight:817.181
Hs Code.:

Synonyms:(2RS)-2-thiophenoxy-2,35:12,13:12,13-hexahydrotrilobin-bis(methoxymethoxy) ether

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Chemical Property of (2RS)-2-thiophenoxy-2,35:12,13:12,13-hexahydrotrilobin-bis(methoxymethoxy) ether

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Technology Process of (2RS)-2-thiophenoxy-2,35:12,13:12,13-hexahydrotrilobin-bis(methoxymethoxy) ether

There total 22 articles about (2RS)-2-thiophenoxy-2,35:12,13:12,13-hexahydrotrilobin-bis(methoxymethoxy) ether 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:

: 59101-25-6
trans-pentadec-4-en-1-ol

: 224037-56-3
(2RS)-2-thiophenoxy-2,35:12,13:12,13-hexahydrotrilobin-bis(methoxymethoxy) ether

Guidance literature:: Multi-step reaction with 21 steps

1: 89 percent / PCC, celite / CH₂Cl₂ / 2 h

2: tetrahydrofuran / 0.5 h / 0 °C

3: propionic acid / xylene / 2 h / Heating

5: 92 percent / TsOH / acetone / 0.5 h / Ambient temperature

6: 94 percent / Et₃N / CH₂Cl₂ / 2 h / -30 - 0 °C

7: TsOH / methanol; H₂O / 16 h / Ambient temperature

8: Py / 2 h / Heating

9: 95 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

10: 2.21 g / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 °C

11: toluene / 16 h / 80 °C

12: 97 percent / DIBAL-H / tetrahydrofuran / 1 h / -78 °C

13: 75 percent / TBHP, (+)-DET, Ti(Oi-Pr)4, molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 16 h / -20 °C

14: 89 percent / DMAP, iPr₂EtN / CH₂Cl₂ / 16 h / Ambient temperature

15: 96 percent / Et₃N / CH₂Cl₂ / 2 h / -30 - 0 °C

16: 91 percent / TsOH / methanol; H₂O / 16 h / Ambient temperature

17: 92 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

18: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, -30 deg C, 1 h, 2.) THF, -78 deg C, 1 h

19: 92 percent / TBAF / tetrahydrofuran / 48 h / 40 °C

20: 89 percent / iPr₂EtN / CH₂Cl₂ / 16 h / 0 - 20 °C

21: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; n-butyllithium; molecular sieve; diethyl (2R,3R)-tartrate; Celite; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; propionic acid; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; xylene;
DOI:10.1021/jo982110i

Reference yield:

: 59101-21-2
(E)-pentadec-4-enoic acid ethyl ester

: 224037-56-3
(2RS)-2-thiophenoxy-2,35:12,13:12,13-hexahydrotrilobin-bis(methoxymethoxy) ether

Guidance literature:: Multi-step reaction with 22 steps

1: LiAlH₄ / diethyl ether / 1 h / 0 - 20 °C

2: 89 percent / PCC, celite / CH₂Cl₂ / 2 h

3: tetrahydrofuran / 0.5 h / 0 °C

4: propionic acid / xylene / 2 h / Heating

6: 92 percent / TsOH / acetone / 0.5 h / Ambient temperature

7: 94 percent / Et₃N / CH₂Cl₂ / 2 h / -30 - 0 °C

8: TsOH / methanol; H₂O / 16 h / Ambient temperature

9: Py / 2 h / Heating

10: 95 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

11: 2.21 g / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 °C

12: toluene / 16 h / 80 °C

13: 97 percent / DIBAL-H / tetrahydrofuran / 1 h / -78 °C

14: 75 percent / TBHP, (+)-DET, Ti(Oi-Pr)4, molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 16 h / -20 °C

15: 89 percent / DMAP, iPr₂EtN / CH₂Cl₂ / 16 h / Ambient temperature

16: 96 percent / Et₃N / CH₂Cl₂ / 2 h / -30 - 0 °C

17: 91 percent / TsOH / methanol; H₂O / 16 h / Ambient temperature

18: 92 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

19: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, -30 deg C, 1 h, 2.) THF, -78 deg C, 1 h

20: 92 percent / TBAF / tetrahydrofuran / 48 h / 40 °C

21: 89 percent / iPr₂EtN / CH₂Cl₂ / 16 h / 0 - 20 °C

22: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; n-butyllithium; molecular sieve; diethyl (2R,3R)-tartrate; Celite; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; propionic acid; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; xylene;
DOI:10.1021/jo982110i

Reference yield:

: 131618-60-5
(trans)-pentadec-4-en-1-al

: 224037-56-3
(2RS)-2-thiophenoxy-2,35:12,13:12,13-hexahydrotrilobin-bis(methoxymethoxy) ether

Guidance literature:: Multi-step reaction with 20 steps

1: tetrahydrofuran / 0.5 h / 0 °C

2: propionic acid / xylene / 2 h / Heating

4: 92 percent / TsOH / acetone / 0.5 h / Ambient temperature

5: 94 percent / Et₃N / CH₂Cl₂ / 2 h / -30 - 0 °C

6: TsOH / methanol; H₂O / 16 h / Ambient temperature

7: Py / 2 h / Heating

8: 95 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

9: 2.21 g / DIBAL-H / tetrahydrofuran; toluene / 1.5 h / -78 °C

10: toluene / 16 h / 80 °C

11: 97 percent / DIBAL-H / tetrahydrofuran / 1 h / -78 °C

12: 75 percent / TBHP, (+)-DET, Ti(Oi-Pr)4, molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 16 h / -20 °C

13: 89 percent / DMAP, iPr₂EtN / CH₂Cl₂ / 16 h / Ambient temperature

14: 96 percent / Et₃N / CH₂Cl₂ / 2 h / -30 - 0 °C

15: 91 percent / TsOH / methanol; H₂O / 16 h / Ambient temperature

16: 92 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

17: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, -30 deg C, 1 h, 2.) THF, -78 deg C, 1 h

18: 92 percent / TBAF / tetrahydrofuran / 48 h / 40 °C

19: 89 percent / iPr₂EtN / CH₂Cl₂ / 16 h / 0 - 20 °C

20: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; n-butyllithium; molecular sieve; diethyl (2R,3R)-tartrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; propionic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; xylene;
DOI:10.1021/jo982110i