(Z)-(4S,5S,6S,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-5,7-dimethyl-undeca-8,10-dien-1-ol

Base Information

Chemical Name:(Z)-(4S,5S,6S,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-5,7-dimethyl-undeca-8,10-dien-1-ol
CAS No.:623926-49-8
Molecular Formula:C₂₇H₄₆O₄Si
Molecular Weight:462.745
Hs Code.:

Synonyms:(Z)-(4S,5S,6S,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-5,7-dimethyl-undeca-8,10-dien-1-ol

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Chemical Property of (Z)-(4S,5S,6S,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-5,7-dimethyl-undeca-8,10-dien-1-ol

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Technology Process of (Z)-(4S,5S,6S,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-5,7-dimethyl-undeca-8,10-dien-1-ol

There total 5 articles about (Z)-(4S,5S,6S,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-5,7-dimethyl-undeca-8,10-dien-1-ol 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%

: 623926-48-7
1-{(Z)-(1S,2S,3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,4-dimethyl-octa-5,7-dienyloxymethyl}-4-methoxy-benzene

: 623926-49-8
(Z)-(4S,5S,6S,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-5,7-dimethyl-undeca-8,10-dien-1-ol

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1016/S0968-0896(03)00186-X

Reference yield:

: 106296-58-6
(2S,3S,4S)-(1-tert-butyldimethylsilanyloxy)-2,4-dimethylhex-5-en-3-ol

: 623926-49-8
(Z)-(4S,5S,6S,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-5,7-dimethyl-undeca-8,10-dien-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 95 percent / HF-pyridine; pyridine / tetrahydrofuran / 12 h / 20 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

4.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 1 h / 20 °C

4.2: 950 mg / tetrahydrofuran / 10 h / 20 °C

5.1: 65 percent / trifllic acid / diethyl ether / -10 - 20 °C

6.1: ozone; pyridine / methanol; CH₂Cl₂ / -78 °C

6.2: dimethyl sulfide / methanol; CH₂Cl₂

7.1: CrCl₂ / tetrahydrofuran / 16 h / 20 °C

8.1: NaH / tetrahydrofuran / 0 - 20 °C

9.1: 92 percent / HF-pyridine; pyridine / tetrahydrofuran / 12 h / 20 °C

With pyridine; chromium dichloride; trifluorormethanesulfonic acid; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; ozone; magnesium; ethylene dibromide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 3.1: Dess-Martin oxidation / 4.2: Grignard reaction / 7.1: Nozaki-Hiyama reaction;
DOI:10.1016/S0968-0896(03)00186-X

Reference yield:

: 623926-29-4
(2R,3S,4S)-3-(tert-butyldimethylsilanyloxy)-2,4-dimethylhex-5-enal

: 623926-49-8
(Z)-(4S,5S,6S,7S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-5,7-dimethyl-undeca-8,10-dien-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 1 h / 20 °C

1.2: 950 mg / tetrahydrofuran / 10 h / 20 °C

2.1: 65 percent / trifllic acid / diethyl ether / -10 - 20 °C

3.1: ozone; pyridine / methanol; CH₂Cl₂ / -78 °C

3.2: dimethyl sulfide / methanol; CH₂Cl₂

4.1: CrCl₂ / tetrahydrofuran / 16 h / 20 °C

5.1: NaH / tetrahydrofuran / 0 - 20 °C

6.1: 92 percent / HF-pyridine; pyridine / tetrahydrofuran / 12 h / 20 °C

With pyridine; chromium dichloride; trifluorormethanesulfonic acid; sodium hydride; pyridine hydrogenfluoride; ozone; magnesium; ethylene dibromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.2: Grignard reaction / 4.1: Nozaki-Hiyama reaction;
DOI:10.1016/S0968-0896(03)00186-X