methyl-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(E),14(Z)-eicosatetraenoate

Base Information

• Chemical Name: methyl-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(E),14(Z)-eicosatetraenoate
• CAS No.: 218162-94-8
• Molecular Formula: C₃₉H₅₄O₃S₂Si
• Molecular Weight: 663.073
• Mol file: 218162-94-8.mol

Synonyms:

Chemical Property of methyl-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(E),14(Z)-eicosatetraenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(E),14(Z)-eicosatetraenoate

There total 9 articles about methyl-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(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:

2(S)-<(tert-butyldiphenylsilyl)oxy>-4(Z)-decenal (100428-41-9) → methyl-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(E),14(Z)-eicosatetraenoate (218162-94-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH / 1.) benzene, room temperature, 1 h, 2.) benzene, room temperature, 3 h

2: 96 percent / DIBAL-H / CH₂Cl₂ / 1.) -60 deg C, 15 min, 2.) -> -20 deg C, 1 h

3: CBr₄, DIPHOS / CH₂Cl₂ / 0.5 h / 0 °C

4: CH₂Cl₂ / 18 h / Ambient temperature

5: 1.) sodium hexamethyldisilazide, 2.) HMPA / 1.) THF, -98 deg C, 15 min, 2.) THF, -98 deg C (15 min), -> 0 deg C (1 h)

With N,N,N,N,N,N-hexamethylphosphoric triamide; carbon tetrabromide; temephos; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1021/jo9813282

Reference yield:

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal (93292-41-2) → methyl-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(E),14(Z)-eicosatetraenoate (218162-94-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 84 percent / periodic acid / tetrahydrofuran; diethyl ether / 1.) 0 deg C, 3 min, 2.) room temp., 5 min

2: 1.) sodium hexamethyldisilazide, 2.) HMPA / 1.) THF, room temperature, 30 min, 2.) THF, -78 deg C (2 h), -> 0 deg C (2 h)

3: 98 percent / periodic acid / diethyl ether; tetrahydrofuran / Ambient temperature

4: 1.) NaH / 1.) benzene, room temperature, 1 h, 2.) benzene, room temperature, 3 h

5: 96 percent / DIBAL-H / CH₂Cl₂ / 1.) -60 deg C, 15 min, 2.) -> -20 deg C, 1 h

6: CBr₄, DIPHOS / CH₂Cl₂ / 0.5 h / 0 °C

7: CH₂Cl₂ / 18 h / Ambient temperature

8: 1.) sodium hexamethyldisilazide, 2.) HMPA / 1.) THF, -98 deg C, 15 min, 2.) THF, -98 deg C (15 min), -> 0 deg C (1 h)

With N,N,N,N,N,N-hexamethylphosphoric triamide; carbon tetrabromide; temephos; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; periodic acid; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo9813282

Reference yield:

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose (93292-42-3) → methyl-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(E),14(Z)-eicosatetraenoate (218162-94-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) sodium hexamethyldisilazide, 2.) HMPA / 1.) THF, room temperature, 30 min, 2.) THF, -78 deg C (2 h), -> 0 deg C (2 h)

2: 98 percent / periodic acid / diethyl ether; tetrahydrofuran / Ambient temperature

3: 1.) NaH / 1.) benzene, room temperature, 1 h, 2.) benzene, room temperature, 3 h

4: 96 percent / DIBAL-H / CH₂Cl₂ / 1.) -60 deg C, 15 min, 2.) -> -20 deg C, 1 h

5: CBr₄, DIPHOS / CH₂Cl₂ / 0.5 h / 0 °C

6: CH₂Cl₂ / 18 h / Ambient temperature

7: 1.) sodium hexamethyldisilazide, 2.) HMPA / 1.) THF, -98 deg C, 15 min, 2.) THF, -98 deg C (15 min), -> 0 deg C (1 h)

With N,N,N,N,N,N-hexamethylphosphoric triamide; carbon tetrabromide; temephos; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; periodic acid; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo9813282

upstream raw materials:

methyl-5,5-(dimethylenedithio)-6(E)-8-oxo-7-octenoate

2(S)-<(tert-butyldiphenylsilyl)oxy>-4(Z)-decenal

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal

Refernces