methyl 11(S)-<(tert-butyldiphenylsilyl)oxy>-5(Z),8(Z),12(E),14(Z)-eicosatetraenoate

Base Information

• Chemical Name: methyl 11(S)-<(tert-butyldiphenylsilyl)oxy>-5(Z),8(Z),12(E),14(Z)-eicosatetraenoate
• CAS No.: 100818-50-6
• Molecular Formula: C₃₇H₅₂O₃Si
• Molecular Weight: 572.904
• Mol file: 100818-50-6.mol

Synonyms:

Chemical Property of methyl 11(S)-<(tert-butyldiphenylsilyl)oxy>-5(Z),8(Z),12(E),14(Z)-eicosatetraenoate

Chemical Property:

Purity/Quality:

99% ，98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 11(S)-<(tert-butyldiphenylsilyl)oxy>-5(Z),8(Z),12(E),14(Z)-eicosatetraenoate

There total 15 articles about methyl 11(S)-<(tert-butyldiphenylsilyl)oxy>-5(Z),8(Z),12(E),14(Z)-eicosatetraenoate 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:

hexyltriphenylphosphonium bromide (4762-26-9) → methyl 11(S)-<(tert-butyldiphenylsilyl)oxy>-5(Z),8(Z),12(E),14(Z)-eicosatetraenoate (100818-50-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1.) THF, from -78 deg C to RT, 30 min, 2.) THF, -78 deg C, 15 min

2: 1.) silver nitrate, N-chlorosuccinimide, 2.) DMSO / 1.) MeCN, H₂O, -10 deg C, 10 min, 2.) MeCN, H₂O, -10 deg C, 10 min

3: tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 60 min, 2.) 60 min, RT

4: sodium bicarbonate / 1 h / Ambient temperature

With N-chloro-succinimide; n-butyllithium; sodium hydrogencarbonate; silver nitrate; dimethyl sulfoxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/jo00375a009

Reference yield:

4(S)-<(tert-butyldiphenylsilyl)oxy>-6,6-bis(ethylthio)-hex-2(E)-enal (100818-44-8) → methyl 11(S)-<(tert-butyldiphenylsilyl)oxy>-5(Z),8(Z),12(E),14(Z)-eicosatetraenoate (100818-50-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1.) THF, from -78 deg C to RT, 30 min, 2.) THF, -78 deg C, 15 min

2: 1.) silver nitrate, N-chlorosuccinimide, 2.) DMSO / 1.) MeCN, H₂O, -10 deg C, 10 min, 2.) MeCN, H₂O, -10 deg C, 10 min

3: tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 60 min, 2.) 60 min, RT

4: sodium bicarbonate / 1 h / Ambient temperature

With N-chloro-succinimide; n-butyllithium; sodium hydrogencarbonate; silver nitrate; dimethyl sulfoxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/jo00375a009

Reference yield:

2-deoxy-3-O-<(tert-butyldiphenylsilyl)oxy>-4,5-dihydroxy-D-erythro-pentose diethyl dithioacetal (100818-42-6) → methyl 11(S)-<(tert-butyldiphenylsilyl)oxy>-5(Z),8(Z),12(E),14(Z)-eicosatetraenoate (100818-50-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 76.8 percent / sodium periodate / tetrahydrofuran; H₂O; acetone / 0.25 h / Ambient temperature

2: 79 percent / benzene / 6.5 h / 70 °C

3: 1.) n-BuLi / 1.) THF, from -78 deg C to RT, 30 min, 2.) THF, -78 deg C, 15 min

4: 1.) silver nitrate, N-chlorosuccinimide, 2.) DMSO / 1.) MeCN, H₂O, -10 deg C, 10 min, 2.) MeCN, H₂O, -10 deg C, 10 min

5: tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 60 min, 2.) 60 min, RT

6: sodium bicarbonate / 1 h / Ambient temperature

With sodium periodate; N-chloro-succinimide; n-butyllithium; sodium hydrogencarbonate; silver nitrate; dimethyl sulfoxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; water; acetone; benzene;

DOI:10.1021/jo00375a009

upstream raw materials:

3(S)-<(tert-butyldiphenylsilyl)oxy>-4(E),6(Z)-dodecadienal

(Z)-8-(Triphenyl-λ⁵-phosphanylidene)-oct-5-enoic acid anion

dimethyl sulfate

2(S)-<(tert-butyldiphenylsilyl)oxy>-4,4-bis(ethylthio)butanal

Refernces

• 1、 Just, George,Wang, Zhi Yuan. "A SIMPLE SYNTHESIS OF METHYL 11(S)- AND 12(S)-HETE". . p. 2993 - 2996. Retrieved 2007/10/02.