(10S)-methyl 10-<(tert-butyldiphenylsilyl)oxy>eicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate

Base Information

Chemical Name:(10S)-methyl 10-<(tert-butyldiphenylsilyl)oxy>eicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate
CAS No.:173289-76-4
Molecular Formula:C₃₇H₅₂O₃Si
Molecular Weight:572.904
Hs Code.:

Synonyms:

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Chemical Property of (10S)-methyl 10-<(tert-butyldiphenylsilyl)oxy>eicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate

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Technology Process of (10S)-methyl 10-<(tert-butyldiphenylsilyl)oxy>eicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate

There total 7 articles about (10S)-methyl 10-<(tert-butyldiphenylsilyl)oxy>eicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate 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:

: 85924-42-1
[(3Z)-3-nonen-1-yl]triphenylphosphonium bromide

: 173289-76-4
(10S)-methyl 10-<(tert-butyldiphenylsilyl)oxy>eicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) lithium bis(trimethylsilyl)amide / 1) THF, toluene, 0 deg C, 30 min; 2) THF, toluene, 0 deg C, 2 h

2: 83 percent / aq. HCl / methanol / 2 h / 0 °C

3: 75 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / Ambient temperature

4: 81 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h / Ambient temperature

5: 76 percent / pyridinium p-toluenesulfonate / ethanol / 15 h / 60 °C

6: 73 percent / pyridinium chlorochromate, sodium acetate, 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / Ambient temperature

7: 1.) lithium bis(trimethylsilyl)amide / 1) THF, 0 deg C, 35 min, rt, 30 min; 2) THF, 0 deg C, 3 h

With hydrogenchloride; dmap; 4 A molecular sieve; sodium acetate; pyridinium p-toluenesulfonate; pyridinium chlorochromate; lithium hexamethyldisilazane; In methanol; ethanol; dichloromethane;
DOI:10.1021/jo951061w

Reference yield:

: 173289-71-9
(2S)-(Z,Z)-3,6-dodecadiene-1,2-diol

: 173289-76-4
(10S)-methyl 10-<(tert-butyldiphenylsilyl)oxy>eicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / Ambient temperature

2: 81 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h / Ambient temperature

3: 76 percent / pyridinium p-toluenesulfonate / ethanol / 15 h / 60 °C

4: 73 percent / pyridinium chlorochromate, sodium acetate, 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 1.) lithium bis(trimethylsilyl)amide / 1) THF, 0 deg C, 35 min, rt, 30 min; 2) THF, 0 deg C, 3 h

With dmap; 4 A molecular sieve; sodium acetate; pyridinium p-toluenesulfonate; pyridinium chlorochromate; lithium hexamethyldisilazane; In ethanol; dichloromethane;
DOI:10.1021/jo951061w

Reference yield:

: 173289-70-8
(Z,Z)-4-deca-1,4-dien-1-yl-2,2-dimethyl-1,3-dioxolane

: 173289-76-4
(10S)-methyl 10-<(tert-butyldiphenylsilyl)oxy>eicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / aq. HCl / methanol / 2 h / 0 °C

2: 75 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / Ambient temperature

3: 81 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h / Ambient temperature

4: 76 percent / pyridinium p-toluenesulfonate / ethanol / 15 h / 60 °C

5: 73 percent / pyridinium chlorochromate, sodium acetate, 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 1.) lithium bis(trimethylsilyl)amide / 1) THF, 0 deg C, 35 min, rt, 30 min; 2) THF, 0 deg C, 3 h

With hydrogenchloride; dmap; 4 A molecular sieve; sodium acetate; pyridinium p-toluenesulfonate; pyridinium chlorochromate; lithium hexamethyldisilazane; In methanol; ethanol; dichloromethane;
DOI:10.1021/jo951061w