(4E,6E)-(2S,3S,8R,9S,10S)-3-Hydroxy-9-(4-methoxy-benzyloxy)-2,4,6,8,10-pentamethyl-icosa-4,6-dienethioic acid S-ethyl ester

Base Information

Chemical Name:(4E,6E)-(2S,3S,8R,9S,10S)-3-Hydroxy-9-(4-methoxy-benzyloxy)-2,4,6,8,10-pentamethyl-icosa-4,6-dienethioic acid S-ethyl ester
CAS No.:331626-16-5
Molecular Formula:C₃₅H₅₈O₄S
Molecular Weight:574.909
Hs Code.:

Synonyms:(4E,6E)-(2S,3S,8R,9S,10S)-3-Hydroxy-9-(4-methoxy-benzyloxy)-2,4,6,8,10-pentamethyl-icosa-4,6-dienethioic acid S-ethyl ester

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Chemical Property of (4E,6E)-(2S,3S,8R,9S,10S)-3-Hydroxy-9-(4-methoxy-benzyloxy)-2,4,6,8,10-pentamethyl-icosa-4,6-dienethioic acid S-ethyl ester

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Technology Process of (4E,6E)-(2S,3S,8R,9S,10S)-3-Hydroxy-9-(4-methoxy-benzyloxy)-2,4,6,8,10-pentamethyl-icosa-4,6-dienethioic acid S-ethyl ester

There total 18 articles about (4E,6E)-(2S,3S,8R,9S,10S)-3-Hydroxy-9-(4-methoxy-benzyloxy)-2,4,6,8,10-pentamethyl-icosa-4,6-dienethioic acid S-ethyl 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:

: 63584-42-9,130535-66-9,63584-50-9
(Z)-1-ethylthio-1-(trimethylsiloxy)propene

: 331626-13-2
(2E,4E)-(6R,7S,8S)-7-(4-Methoxy-benzyloxy)-2,4,6,8-tetramethyl-octadeca-2,4-dienal

: 331626-16-5
(4E,6E)-(2S,3S,8R,9S,10S)-3-Hydroxy-9-(4-methoxy-benzyloxy)-2,4,6,8,10-pentamethyl-icosa-4,6-dienethioic acid S-ethyl ester

Guidance literature:: With tin(II) trifluoromethanesulfonate; dibutyltin diacetate; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; In dichloromethane; at -78 ℃;
DOI:10.1021/ja0057272

Reference yield:

: 112-31-2
caprinaldehyde

: 331626-16-5
(4E,6E)-(2S,3S,8R,9S,10S)-3-Hydroxy-9-(4-methoxy-benzyloxy)-2,4,6,8,10-pentamethyl-icosa-4,6-dienethioic acid S-ethyl ester

Guidance literature:: Multi-step reaction with 17 steps

1: 83 percent / Sn(OTf)2; SnO; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine / CH₂Cl₂ / 5 h / -78 °C

2: pyridine / 1,2-dichloro-ethane / 0.17 h / Heating

3: Bu₃SnH; AIBN / toluene / 0.17 h / 110 °C

4: 5.17 g / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

5: 91 percent / (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

6: Sn(OTf)2; Bu₂Sn(OAc)2; (S)-1-methyl-2-[(N-naphthylamino)-methyl]pyrrolidine / CH₂Cl₂ / -78 °C

7: LiBH₄ / tetrahydrofuran / -5 °C

8: TsOH / CH₂Cl₂ / 20 °C

9: DIBAL / CH₂Cl₂ / 20 °C

10: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

11: tetrahydrofuran / Heating

12: DIBAL / CH₂Cl₂; hexane / -78 °C

13: TPAP; NMO / CH₂Cl₂ / 20 °C

14: tetrahydrofuran / Heating

15: DIBAL / CH₂Cl₂; hexane / -78 °C

16: TPAP; NMO / CH₂Cl₂ / 20 °C

17: Sn(OTf)2; Bu₂Sn(OAc)2; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine / CH₂Cl₂ / -78 °C

With pyridine; lithium aluminium tetrahydride; lithium borohydride; tin(II) trifluoromethanesulfonate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tin(II) oxide; diisobutylaluminium hydride; dibutyltin diacetate; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; toluene; 5: Swern oxidation / 10: Swern oxidation / 11: Wittig olefination / 14: Wittig olefination;
DOI:10.1021/ja0057272

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 331626-16-5
(4E,6E)-(2S,3S,8R,9S,10S)-3-Hydroxy-9-(4-methoxy-benzyloxy)-2,4,6,8,10-pentamethyl-icosa-4,6-dienethioic acid S-ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: TsOH / CH₂Cl₂ / 20 °C

2: DIBAL / CH₂Cl₂ / 20 °C

3: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

4: tetrahydrofuran / Heating

5: DIBAL / CH₂Cl₂; hexane / -78 °C

6: TPAP; NMO / CH₂Cl₂ / 20 °C

7: tetrahydrofuran / Heating

8: DIBAL / CH₂Cl₂; hexane / -78 °C

9: TPAP; NMO / CH₂Cl₂ / 20 °C

10: Sn(OTf)2; Bu₂Sn(OAc)2; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine / CH₂Cl₂ / -78 °C

With tin(II) trifluoromethanesulfonate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; diisobutylaluminium hydride; dibutyltin diacetate; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; hexane; dichloromethane; 3: Swern oxidation / 4: Wittig olefination / 7: Wittig olefination;
DOI:10.1021/ja0057272