Methyl 15S-(tert-butyldiphenylsilyloxy)-7R-methoxy-2-methyl-2E,4E,10E-hexadecatrienoate

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Chemical Name:Methyl 15S-(tert-butyldiphenylsilyloxy)-7R-methoxy-2-methyl-2E,4E,10E-hexadecatrienoate
CAS No.:345653-60-3
Molecular Formula:C₃₅H₅₀O₄Si
Molecular Weight:562.865
Hs Code.:

Synonyms:Methyl 15S-(tert-butyldiphenylsilyloxy)-7R-methoxy-2-methyl-2E,4E,10E-hexadecatrienoate

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Chemical Property of Methyl 15S-(tert-butyldiphenylsilyloxy)-7R-methoxy-2-methyl-2E,4E,10E-hexadecatrienoate

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Technology Process of Methyl 15S-(tert-butyldiphenylsilyloxy)-7R-methoxy-2-methyl-2E,4E,10E-hexadecatrienoate

There total 14 articles about Methyl 15S-(tert-butyldiphenylsilyloxy)-7R-methoxy-2-methyl-2E,4E,10E-hexadecatrienoate 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: 65.0%

: 121666-37-3
<3-(Methoxycarbonyl)-2-butenyl>triphenylphosphoniumbromid

: 345653-88-5
11(S)-(tert-Butyldiphenylsilyloxy)-3R-methoxy-6E-dodecenal

: 345653-60-3
Methyl 15S-(tert-butyldiphenylsilyloxy)-7R-methoxy-2-methyl-2E,4E,10E-hexadecatrienoate

Guidance literature:: <3-(Methoxycarbonyl)-2-butenyl>triphenylphosphoniumbromid; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 2h;

11(S)-(tert-Butyldiphenylsilyloxy)-3R-methoxy-6E-dodecenal; In tetrahydrofuran; at -78 - 20 ℃; for 20h;

With iodine; In chloroform; at 20 ℃; for 24h; Further stages.;
DOI:10.1021/np000502q

Reference yield:

: 97974-23-7
(S)-2-(tert-butyldiphenylsilyloxy)-1-propanol

: 345653-60-3
Methyl 15S-(tert-butyldiphenylsilyloxy)-7R-methoxy-2-methyl-2E,4E,10E-hexadecatrienoate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 64.42 g / pyridine / CH₂Cl₂ / 24.5 h / 0 - 20 °C

2.1: 93 percent / LiBr / tetrahydrofuran / 47 h / Heating

3.1: 76 percent / Li₂CuCl₄ / tetrahydrofuran; diethyl ether / 17 h / 20 °C

4.1: BH₃*THF / tetrahydrofuran / 1 h / 0 - 20 °C

4.2: 68 percent / Br₂; NaOMe / tetrahydrofuran; methanol / 5 - 20 °C

5.1: 75 percent / toluene / 48 h / Heating

6.1: PhLi / tetrahydrofuran; diethyl ether / 0.33 h / 20 °C

6.2: 54 percent / tetrahydrofuran; diethyl ether / 0.67 h / -40 - -30 °C

7.1: 80 percent / aq. AcOH / tetrahydrofuran / 47 h / Heating

8.1: 32 percent / Co(PPh₃)4 / tetrahydrofuran / 0.17 h / 0 °C

9.1: 69 percent / K₂CO₃ / 0.5 h / 0 °C

10.1: 99 percent / molecular sieves 4 Angstroem; proton sponge / CH₂Cl₂ / 3 h / 20 °C

11.1: DIBAL / CH₂Cl₂ / 0.08 h / -78 °C

11.2: 87 percent / molecular sieves 4 Angstroem; PDC / CH₂Cl₂ / 1 h / 20 °C

12.1: NaH / tetrahydrofuran / 2 h / 20 °C

12.2: tetrahydrofuran / 20 h / -78 - 20 °C

With pyridine; borane-THF; dilithium tetrachlorocuprate; Proton Sponge; tristriphenylphosphine cobalt chloride; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; phenyllithium; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 6.2: Wittig-Schlosser reaction / 8.1: Reformatsky reaction / 12.2: Wittig reaction;
DOI:10.1021/np000502q

Reference yield:

: 102732-44-5
ethyl (S)-2-(tert-butyldiphenylsilyloxy)propanoate

: 345653-60-3
Methyl 15S-(tert-butyldiphenylsilyloxy)-7R-methoxy-2-methyl-2E,4E,10E-hexadecatrienoate

Guidance literature:: Multi-step reaction with 13 steps

1.1: 100 percent / BH₃*THF / tetrahydrofuran / 2 h / Heating

2.1: 64.42 g / pyridine / CH₂Cl₂ / 24.5 h / 0 - 20 °C

3.1: 93 percent / LiBr / tetrahydrofuran / 47 h / Heating

4.1: 76 percent / Li₂CuCl₄ / tetrahydrofuran; diethyl ether / 17 h / 20 °C

5.1: BH₃*THF / tetrahydrofuran / 1 h / 0 - 20 °C

5.2: 68 percent / Br₂; NaOMe / tetrahydrofuran; methanol / 5 - 20 °C

6.1: 75 percent / toluene / 48 h / Heating

7.1: PhLi / tetrahydrofuran; diethyl ether / 0.33 h / 20 °C

7.2: 54 percent / tetrahydrofuran; diethyl ether / 0.67 h / -40 - -30 °C

8.1: 80 percent / aq. AcOH / tetrahydrofuran / 47 h / Heating

9.1: 32 percent / Co(PPh₃)4 / tetrahydrofuran / 0.17 h / 0 °C

10.1: 69 percent / K₂CO₃ / 0.5 h / 0 °C

11.1: 99 percent / molecular sieves 4 Angstroem; proton sponge / CH₂Cl₂ / 3 h / 20 °C

12.1: DIBAL / CH₂Cl₂ / 0.08 h / -78 °C

12.2: 87 percent / molecular sieves 4 Angstroem; PDC / CH₂Cl₂ / 1 h / 20 °C

13.1: NaH / tetrahydrofuran / 2 h / 20 °C

13.2: tetrahydrofuran / 20 h / -78 - 20 °C

With pyridine; borane-THF; dilithium tetrachlorocuprate; Proton Sponge; tristriphenylphosphine cobalt chloride; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; phenyllithium; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 7.2: Wittig-Schlosser reaction / 9.1: Reformatsky reaction / 13.2: Wittig reaction;
DOI:10.1021/np000502q