methyl 5-O-(tert-butyldiphenylsilyl)-10-O-(triphenylmethyl)-3-thia-5(S),10-dihydroxy-6(Z),8(E)-decadienoate

Base Information

• Chemical Name: methyl 5-O-(tert-butyldiphenylsilyl)-10-O-(triphenylmethyl)-3-thia-5(S),10-dihydroxy-6(Z),8(E)-decadienoate
• CAS No.: 111670-28-1
• Molecular Formula: C₄₅H₄₈O₄SSi
• Molecular Weight: 713.025

Synonyms:methyl 5-O-(tert-butyldiphenylsilyl)-10-O-(triphenylmethyl)-3-thia-5(S),10-dihydroxy-6(Z),8(E)-decadienoate

Chemical Property of methyl 5-O-(tert-butyldiphenylsilyl)-10-O-(triphenylmethyl)-3-thia-5(S),10-dihydroxy-6(Z),8(E)-decadienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of methyl 5-O-(tert-butyldiphenylsilyl)-10-O-(triphenylmethyl)-3-thia-5(S),10-dihydroxy-6(Z),8(E)-decadienoate

There total 13 articles about methyl 5-O-(tert-butyldiphenylsilyl)-10-O-(triphenylmethyl)-3-thia-5(S),10-dihydroxy-6(Z),8(E)-decadienoate 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: 96.0%

Methyl thioglycolate (2365-48-2) + 6-O-(tert-butyldiphenylsilyl)-7-iodo-1-O-(triphenylmethyl)-2(E),4(Z)-heptadiene-1,6(S)-diol (111670-27-0) → methyl 5-O-(tert-butyldiphenylsilyl)-10-O-(triphenylmethyl)-3-thia-5(S),10-dihydroxy-6(Z),8(E)-decadienoate (111670-28-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 50 ℃; for 4h;

DOI:10.1139/v87-244

Reference yield:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → methyl 5-O-(tert-butyldiphenylsilyl)-10-O-(triphenylmethyl)-3-thia-5(S),10-dihydroxy-6(Z),8(E)-decadienoate (111670-28-1)

Guidance literature:

Multi-step reaction with 13 steps

2: (i-Pr)2NEt / DMAP / CH₂Cl₂

3: pyridine; CH₂Cl₂

4: DBU / pyridine

5: 92 percent / LDA / tetrahydrofuran / 0 °C

6: 89 percent / triphenylphosphine, DEAD / tetrahydrofuran / Ambient temperature

7: 79 percent / DIBAH / toluene / -10 deg C to room temp.

8: DMAP / pyridine / 50 °C

9: tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

10: 63 percent / triethylamine / CH₂Cl₂ / Ambient temperature

11: 87 percent / (i-Pr)2NEt / CH₂Cl₂ / Ambient temperature

12: 83 percent / NaI / butan-2-one / 70 °C

13: 96 percent / NaH / tetrahydrofuran / 4 h / 50 °C

With tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; lithium diisopropyl amide; diethylazodicarboxylate; dmap; In tetrahydrofuran; pyridine; dichloromethane; toluene; butanone;

DOI:10.1139/v87-244

Reference yield:

ethyl 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetate (79308-52-4) → methyl 5-O-(tert-butyldiphenylsilyl)-10-O-(triphenylmethyl)-3-thia-5(S),10-dihydroxy-6(Z),8(E)-decadienoate (111670-28-1)

Guidance literature:

Multi-step reaction with 12 steps

1: (i-Pr)2NEt / DMAP / CH₂Cl₂

2: pyridine; CH₂Cl₂

3: DBU / pyridine

4: 92 percent / LDA / tetrahydrofuran / 0 °C

5: 89 percent / triphenylphosphine, DEAD / tetrahydrofuran / Ambient temperature

6: 79 percent / DIBAH / toluene / -10 deg C to room temp.

7: DMAP / pyridine / 50 °C

8: tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

9: 63 percent / triethylamine / CH₂Cl₂ / Ambient temperature

10: 87 percent / (i-Pr)2NEt / CH₂Cl₂ / Ambient temperature

11: 83 percent / NaI / butan-2-one / 70 °C

12: 96 percent / NaH / tetrahydrofuran / 4 h / 50 °C

With tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; lithium diisopropyl amide; diethylazodicarboxylate; dmap; In tetrahydrofuran; pyridine; dichloromethane; toluene; butanone;

DOI:10.1139/v87-244

upstream raw materials:

Methyl thioglycolate

6-O-(tert-butyldiphenylsilyl)-7-iodo-1-O-(triphenylmethyl)-2(E),4(Z)-heptadiene-1,6(S)-diol

2-deoxy-D-ribose

ethyl 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetate

Downstream raw materials:

[(3Z,5E,7E,11Z)-(2R,9R)-2,9-Bis-(tert-butyl-diphenyl-silanyloxy)-heptadeca-3,5,7,11-tetraenylsulfanyl]-acetic acid methyl ester

[(2E,4Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-methoxycarbonylmethylsulfanyl-hepta-2,4-dienyl]-triphenyl-phosphonium; bromide

[(3Z,5E)-(R)-7-Bromo-2-(tert-butyl-diphenyl-silanyloxy)-hepta-3,5-dienylsulfanyl]-acetic acid methyl ester

[(3Z,5E,7E,11Z)-(2R,9R)-2,9-Bis-(tert-butyl-diphenyl-silanyloxy)-heptadeca-3,5,7,11-tetraenylsulfanyl]-acetic acid methyl ester

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