(4E,8E,10S,11S)-10-benzyloxymethyloxy-11-<2-(tert-butyldimethylsilyloxy)ethyl>-4,8-dimethyl-1-iodo-13-(p-methoxyphenyl)methoxy-4,8-tridecadiene

Base Information

Chemical Name:(4E,8E,10S,11S)-10-benzyloxymethyloxy-11-<2-(tert-butyldimethylsilyloxy)ethyl>-4,8-dimethyl-1-iodo-13-(p-methoxyphenyl)methoxy-4,8-tridecadiene
CAS No.:128322-22-5
Molecular Formula:C₃₉H₆₁IO₅Si
Molecular Weight:764.9
Hs Code.:

(4E,8E,10S,11S)-10-benzyloxymethyloxy-11-<2-(tert-butyldimethylsilyloxy)ethyl>-4,8-dimethyl-1-iodo-13-(p-methoxyphenyl)methoxy-4,8-tridecadiene

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Chemical Property of (4E,8E,10S,11S)-10-benzyloxymethyloxy-11-<2-(tert-butyldimethylsilyloxy)ethyl>-4,8-dimethyl-1-iodo-13-(p-methoxyphenyl)methoxy-4,8-tridecadiene

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Technology Process of (4E,8E,10S,11S)-10-benzyloxymethyloxy-11-<2-(tert-butyldimethylsilyloxy)ethyl>-4,8-dimethyl-1-iodo-13-(p-methoxyphenyl)methoxy-4,8-tridecadiene

There total 20 articles about (4E,8E,10S,11S)-10-benzyloxymethyloxy-11-<2-(tert-butyldimethylsilyloxy)ethyl>-4,8-dimethyl-1-iodo-13-(p-methoxyphenyl)methoxy-4,8-tridecadiene 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:

: 128322-21-4
Methanesulfonic acid (4E,8E)-(10S,11S)-10-benzyloxymethoxy-13-(tert-butyl-dimethyl-silanyloxy)-11-[2-(4-methoxy-benzyloxy)-ethyl]-4,8-dimethyl-trideca-4,8-dienyl ester

: 128322-22-5
(4E,8E,10S,11S)-10-benzyloxymethyloxy-11-<2-(tert-butyldimethylsilyloxy)ethyl>-4,8-dimethyl-1-iodo-13-(p-methoxyphenyl)methoxy-4,8-tridecadiene

Guidance literature:: With sodium iodide; In acetone;
DOI:10.1016/S0040-4039(01)93503-8

Reference yield:

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 128322-22-5
(4E,8E,10S,11S)-10-benzyloxymethyloxy-11-<2-(tert-butyldimethylsilyloxy)ethyl>-4,8-dimethyl-1-iodo-13-(p-methoxyphenyl)methoxy-4,8-tridecadiene

Guidance literature:: Multi-step reaction with 17 steps

1: 95 percent / CSA / tetrahydrofuran / 15 h / 10 °C

2: 1.) LDA / 1.) hexane, THF, -78 deg C, 40 min, 2.) hexane, THF, -78 deg C, 30 min

3: 53 percent / diisobutylaluminum hydride (DIBAH) / hexane; tetrahydrofuran / 0.5 h

4: 66 percent / NaBH₄ / methanol / 0.33 h / 0 °C

5: 88 percent / imidazole / tetrahydrofuran / 20 h / Ambient temperature

6: 100 percent / diisopropylethylamine / 1,2-dichloro-ethane / 5 h / 60 °C

7: LAH / diethyl ether / 0.5 h / 0 °C

8: NaH / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

9: MgBr / diethyl ether / 7 h / Ambient temperature

10: 99 percent / DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 0.33 h / -70 °C

11: 85 percent / tetrahydrofuran / 1 h

12: 66 percent / Hg(II) acetate / 48 h / 135 °C

13: 76 percent / tetrahydrofuran / 1 h

14: Hg(II) acetate / 48 h / 135 °C

15: 99 percent / NaBH₄ / methanol / 0.5 h / 0 °C

16: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

17: NaI / acetone / 20 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; mercury(II) diacetate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;
DOI:10.1248/cpb.40.1742

Reference yield:

: 128387-70-2
(4S)-4-hydroxy-5-tetrahydropyranyloxy-2-pentenoic acid γ-lactone

: 128322-22-5
(4E,8E,10S,11S)-10-benzyloxymethyloxy-11-<2-(tert-butyldimethylsilyloxy)ethyl>-4,8-dimethyl-1-iodo-13-(p-methoxyphenyl)methoxy-4,8-tridecadiene

Guidance literature:: Multi-step reaction with 16 steps

1: 1.) LDA / 1.) hexane, THF, -78 deg C, 40 min, 2.) hexane, THF, -78 deg C, 30 min

2: 53 percent / diisobutylaluminum hydride (DIBAH) / hexane; tetrahydrofuran / 0.5 h

3: 66 percent / NaBH₄ / methanol / 0.33 h / 0 °C

4: 88 percent / imidazole / tetrahydrofuran / 20 h / Ambient temperature

5: 100 percent / diisopropylethylamine / 1,2-dichloro-ethane / 5 h / 60 °C

6: LAH / diethyl ether / 0.5 h / 0 °C

7: NaH / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

8: MgBr / diethyl ether / 7 h / Ambient temperature

9: 99 percent / DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 0.33 h / -70 °C

10: 85 percent / tetrahydrofuran / 1 h

11: 66 percent / Hg(II) acetate / 48 h / 135 °C

12: 76 percent / tetrahydrofuran / 1 h

13: Hg(II) acetate / 48 h / 135 °C

14: 99 percent / NaBH₄ / methanol / 0.5 h / 0 °C

15: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

16: NaI / acetone / 20 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; mercury(II) diacetate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;
DOI:10.1248/cpb.40.1742