(5S,6R,15S)-(7E,9E,11Z,13E)-15-O-tert-butyldiphenylsilyl-5,6-O-carbonyllipoxin A₄ ethyl ester

Base Information

• Chemical Name: (5S,6R,15S)-(7E,9E,11Z,13E)-15-O-tert-butyldiphenylsilyl-5,6-O-carbonyllipoxin A₄ ethyl ester
• CAS No.: 94235-56-0
• Molecular Formula: C₃₉H₅₂O₆Si
• Molecular Weight: 644.924
• Mol file: 94235-56-0.mol

Synonyms:

Chemical Property of (5S,6R,15S)-(7E,9E,11Z,13E)-15-O-tert-butyldiphenylsilyl-5,6-O-carbonyllipoxin A₄ ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R,15S)-(7E,9E,11Z,13E)-15-O-tert-butyldiphenylsilyl-5,6-O-carbonyllipoxin A₄ ethyl ester

There total 21 articles about (5S,6R,15S)-(7E,9E,11Z,13E)-15-O-tert-butyldiphenylsilyl-5,6-O-carbonyllipoxin A₄ ethyl ester 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:

ethyl 3-lithiopropiolate (72036-30-7) → (5S,6R,15S)-(7E,9E,11Z,13E)-15-O-tert-butyldiphenylsilyl-5,6-O-carbonyllipoxin A4 ethyl ester (94235-56-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / BF₃*OEt₂ / diethyl ether / 1 h / -100 °C

2: 81 percent / pyridine / Ambient temperature

3: 95 percent / H₂ / PtO₂ / ethanol

4: aq.TFA / 1 h / 0 °C

5: PTSA / toluene / 6 h / Ambient temperature

7: 1) KHMDS / 1) THF, -105 deg C, 2) HMPA, -100 to -40 deg C

With pyridine; boron trifluoride diethyl etherate; hydrogen; potassium hexamethylsilazane; toluene-4-sulfonic acid; trifluoroacetic acid; platinum(IV) oxide; In diethyl ether; ethanol; toluene;

DOI:10.1016/S0040-4039(00)92034-3

Reference yield:

(S)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-pent-2-ynoic acid ethyl ester (133988-95-1) → (5S,6R,15S)-(7E,9E,11Z,13E)-15-O-tert-butyldiphenylsilyl-5,6-O-carbonyllipoxin A4 ethyl ester (94235-56-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 81 percent / pyridine / Ambient temperature

2: 95 percent / H₂ / PtO₂ / ethanol

3: aq.TFA / 1 h / 0 °C

4: PTSA / toluene / 6 h / Ambient temperature

6: 1) KHMDS / 1) THF, -105 deg C, 2) HMPA, -100 to -40 deg C

With pyridine; hydrogen; potassium hexamethylsilazane; toluene-4-sulfonic acid; trifluoroacetic acid; platinum(IV) oxide; In ethanol; toluene;

DOI:10.1016/S0040-4039(00)92034-3

Reference yield:

Ethyl (5S,6R)-5-ethoxycarbonyloxy-6,7-O-isopropylidene-6,7-dihydroxyhept-2-ynoate (146444-84-0) → (5S,6R,15S)-(7E,9E,11Z,13E)-15-O-tert-butyldiphenylsilyl-5,6-O-carbonyllipoxin A4 ethyl ester (94235-56-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / H₂ / PtO₂ / ethanol

2: aq.TFA / 1 h / 0 °C

3: PTSA / toluene / 6 h / Ambient temperature

5: 1) KHMDS / 1) THF, -105 deg C, 2) HMPA, -100 to -40 deg C

With hydrogen; potassium hexamethylsilazane; toluene-4-sulfonic acid; trifluoroacetic acid; platinum(IV) oxide; In ethanol; toluene;

DOI:10.1016/S0040-4039(00)92034-3

upstream raw materials:

4-[(4S,5R)-2-Oxo-5-((1E,3E)-5-oxo-penta-1,3-dienyl)-[1,3]dioxolan-4-yl]-butyric acid ethyl ester

<(4S)-(2E)-4-tert-butyldiphenylsilyloxy-2-nonen-yl>triphenylphosphonium bromide

[(S)-oct-1-en-3-yloxy](tert-butyl)diphenylsilane

(S)-2-(tert-butyldiphenylsilyloxy)heptanal