(2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienoic acid N-methoxy-N-methyl-amide

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Chemical Name:(2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienoic acid N-methoxy-N-methyl-amide
CAS No.:445306-61-6
Molecular Formula:C₃₄H₄₇NO₆Si
Molecular Weight:593.836
Hs Code.:

(2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienoic acid N-methoxy-N-methyl-amide

Synonyms:(2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienoic acid N-methoxy-N-methyl-amide

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Chemical Property of (2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienoic acid N-methoxy-N-methyl-amide

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Technology Process of (2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienoic acid N-methoxy-N-methyl-amide

There total 21 articles about (2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienoic acid N-methoxy-N-methyl-amide 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: 92.0%

: 124931-12-0
diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate

: 445306-60-5
(3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enal

: 445306-61-6
(2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienoic acid N-methoxy-N-methyl-amide

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0040-4039(02)00472-0

Reference yield:

: 302554-87-6
(S)-2-allyloxy-4-methyl-1-trityloxy-4-pentene

: 445306-61-6
(2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienoic acid N-methoxy-N-methyl-amide

Guidance literature:: Multi-step reaction with 9 steps

1: Cl₂(PCy₃)2Ru=CHPh / tetrahydrofuran / 20 °C

2: 84 percent / HCl gas / CH₂Cl₂ / 0.5 h / -10 °C

3: Et₃N; pyr*SO₃ / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 - 5 °C

4: 81 percent / Et₃N; LiCl / tetrahydrofuran / 15 h / 0 °C

5: 94 percent / NaBH₄; CeCl₃*7H₂O / ethanol / 0.17 h / -78 °C

6: iPr₂NEt; TBAI / dimethylformamide / 16 h / 20 °C

7: 4.17 g / TsOH / methanol / 0.5 h / 20 °C

8: 98 percent / SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

9: 92 percent / NaH / tetrahydrofuran / 1.5 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; pyridine-SO₃ complex; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 3: Parikh-Doering oxidation / 8: Parikh-Doering oxidation / 9: Wittig-Horner-Emmons olefination;
DOI:10.1021/jo026743f

Reference yield:

: 206660-79-9
(S)-4-methyl-1-(trityloxy)pent-4-en-2-ol

: 445306-61-6
(2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienoic acid N-methoxy-N-methyl-amide

Guidance literature:: Multi-step reaction with 10 steps

1.1: t-BuOK / tetrahydrofuran / 1 h / 20 - 45 °C

1.2: 92 percent / tetrahydrofuran / 1.5 h / 20 °C

2.1: Cl₂(PCy₃)2Ru=CHPh / tetrahydrofuran / 20 °C

3.1: 84 percent / HCl gas / CH₂Cl₂ / 0.5 h / -10 °C

4.1: Et₃N; pyr*SO₃ / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 - 5 °C

5.1: 81 percent / Et₃N; LiCl / tetrahydrofuran / 15 h / 0 °C

6.1: 94 percent / NaBH₄; CeCl₃*7H₂O / ethanol / 0.17 h / -78 °C

7.1: iPr₂NEt; TBAI / dimethylformamide / 16 h / 20 °C

8.1: 4.17 g / TsOH / methanol / 0.5 h / 20 °C

9.1: 98 percent / SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

10.1: 92 percent / NaH / tetrahydrofuran / 1.5 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; pyridine-SO₃ complex; potassium tert-butylate; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 4.1: Parikh-Doering oxidation / 9.1: Parikh-Doering oxidation / 10.1: Wittig-Horner-Emmons olefination;
DOI:10.1021/jo026743f