(2S)-1-<(tert-butyldimethylsilyl)oxy>-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadiene

Base Information

• Chemical Name: (2S)-1-<(tert-butyldimethylsilyl)oxy>-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadiene
• CAS No.: 173289-73-1
• Molecular Formula: C₃₄H₅₄O₂Si₂
• Molecular Weight: 550.973
• Mol file: 173289-73-1.mol

Synonyms:(2S)-1-<(tert-butyldimethylsilyl)oxy>-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadiene

Chemical Property of (2S)-1-<(tert-butyldimethylsilyl)oxy>-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadiene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-1-<(tert-butyldimethylsilyl)oxy>-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadiene

There total 5 articles about (2S)-1-<(tert-butyldimethylsilyl)oxy>-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadiene 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: 81.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (2S)-1-<(tert-butyldimethylsilyl)oxy>-(Z,Z)-3,6-dodecadien-2-ol (173289-72-0) → (2S)-1-<(tert-butyldimethylsilyl)oxy>-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadiene (173289-73-1)

Guidance literature:

With dmap; In dichloromethane; for 15h; Ambient temperature;

DOI:10.1021/jo951061w

Reference yield:

[(3Z)-3-nonen-1-yl]triphenylphosphonium bromide (85924-42-1) → (2S)-1-<(tert-butyldimethylsilyl)oxy>-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadiene (173289-73-1)

Guidance literature:

Multi-step reaction with 4 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

With hydrogenchloride; dmap; lithium hexamethyldisilazane; In methanol; dichloromethane;

DOI:10.1021/jo951061w

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S)-1-<(tert-butyldimethylsilyl)oxy>-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadiene (173289-73-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With dmap; In dichloromethane;

DOI:10.1021/jo951061w

upstream raw materials:

tert-butylchlorodiphenylsilane

(2S)-1-<(tert-butyldimethylsilyl)oxy>-(Z,Z)-3,6-dodecadien-2-ol

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

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

(2S)-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadien-1-al

(10S)-(-)hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid

(2S)-2-<(tert-butyldiphenylsilyl)oxy>-(Z,Z)-3,6-dodecadien-1-ol