(Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-8-(4-methoxybenzyloxy)-9-((Z)-5-trimethylsilanylpent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine

Base Information

• Chemical Name: (Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-8-(4-methoxybenzyloxy)-9-((Z)-5-trimethylsilanylpent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine
• CAS No.: 876064-75-4
• Molecular Formula: C₄₂H₅₆O₄Si₂
• Molecular Weight: 681.075
• Mol file: 876064-75-4.mol

Synonyms:(Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-8-(4-methoxybenzyloxy)-9-((Z)-5-trimethylsilanylpent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine

Chemical Property of (Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-8-(4-methoxybenzyloxy)-9-((Z)-5-trimethylsilanylpent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-8-(4-methoxybenzyloxy)-9-((Z)-5-trimethylsilanylpent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine

There total 19 articles about (Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-8-(4-methoxybenzyloxy)-9-((Z)-5-trimethylsilanylpent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine 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: 97.0%

(Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-((Z)-3-iodoprop-3-enyl)-8-(4-methoxybenzyloxy)-2,3,4,7,8,9-hexahydrooxonine (1033036-66-6) + trimethylsilylacetylene (1066-54-2) → (Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-8-(4-methoxybenzyloxy)-9-((Z)-5-trimethylsilanylpent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine (876064-75-4)

Guidance literature:

With copper(l) iodide; diethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; at 20 ℃;

DOI:10.1055/s-2005-918470

Reference yield:

methyl (+)-(3R,4R)-epoxyhexanoate (876064-66-3) → (Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-8-(4-methoxybenzyloxy)-9-((Z)-5-trimethylsilanylpent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine (876064-75-4)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 85 percent / aq. H₂SO₄

2.1: 96 percent / imidazole / dimethylformamide

3.1: 90 percent / DIBAL-H / tetrahydrofuran / -78 - 20 °C

4.1: 91 percent / tetrahydrofuran

5.1: 90 percent / PPTS / toluene / Heating

6.1: 100 percent / aq. NaIO₄ / methanol; CH₂Cl₂

7.1: 85 percent / DBU / toluene / Heating

8.1: KHMDS / toluene / -78 °C

8.2: (+/-)-2-(phenylsulfonyl)-3-phenyloxaziridine / toluene

8.3: 79 percent / CSA / toluene

9.1: 98 percent / Et₃N / tetrahydrofuran

10.1: 90 percent / DMAP / tetrahydrofuran / -40 - 20 °C

11.1: 99 percent / TBAF / tetrahydrofuran / 20 °C

12.1: 100 percent / NH₄Cl

13.1: (PPh₃)3RhCl / tetrahydrofuran / Heating

13.2: 80 percent / aq. H₂O₂; KOH / tetrahydrofuran; methanol

14.1: 95 percent / PPTS / benzene / Heating

15.1: 86 percent / DIBAL-H / CH₂Cl₂ / -78 - -15 °C

16.1: 100 percent / Et₃N / CH₂Cl₂

17.1: 99 percent / dimethylformamide / 60 °C

18.1: 100 percent / DIBAL-H / toluene / -78 - -15 °C

19.1: 73 percent / NaHMDS; DMPU / tetrahydrofuran / -78 - 20 °C

20.1: 97 percent / CuI; Et₂NH / Pd(PPh₃)4 / 20 °C

With 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium periodate; copper(l) iodide; sulfuric acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; ammonium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; diethylamine; triethylamine; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 7.1: Claisen rearrangement / 19.1: Stork-Wittig reaction / 20.1: Sonogashira reaction;

DOI:10.1055/s-2005-918470

Reference yield:

(4R,5S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-ethyl-dihydro-furan-2-one (876064-55-0) → (Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-8-(4-methoxybenzyloxy)-9-((Z)-5-trimethylsilanylpent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine (876064-75-4)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 90 percent / DIBAL-H / tetrahydrofuran / -78 - 20 °C

2.1: 91 percent / tetrahydrofuran

3.1: 90 percent / PPTS / toluene / Heating

4.1: 100 percent / aq. NaIO₄ / methanol; CH₂Cl₂

5.1: 85 percent / DBU / toluene / Heating

6.1: KHMDS / toluene / -78 °C

6.2: (+/-)-2-(phenylsulfonyl)-3-phenyloxaziridine / toluene

6.3: 79 percent / CSA / toluene

7.1: 98 percent / Et₃N / tetrahydrofuran

8.1: 90 percent / DMAP / tetrahydrofuran / -40 - 20 °C

9.1: 99 percent / TBAF / tetrahydrofuran / 20 °C

10.1: 100 percent / NH₄Cl

11.1: (PPh₃)3RhCl / tetrahydrofuran / Heating

11.2: 80 percent / aq. H₂O₂; KOH / tetrahydrofuran; methanol

12.1: 95 percent / PPTS / benzene / Heating

13.1: 86 percent / DIBAL-H / CH₂Cl₂ / -78 - -15 °C

14.1: 100 percent / Et₃N / CH₂Cl₂

15.1: 99 percent / dimethylformamide / 60 °C

16.1: 100 percent / DIBAL-H / toluene / -78 - -15 °C

17.1: 73 percent / NaHMDS; DMPU / tetrahydrofuran / -78 - 20 °C

18.1: 97 percent / CuI; Et₂NH / Pd(PPh₃)4 / 20 °C

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium periodate; copper(l) iodide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; ammonium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; diethylamine; triethylamine; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 5.1: Claisen rearrangement / 17.1: Stork-Wittig reaction / 18.1: Sonogashira reaction;

DOI:10.1055/s-2005-918470

upstream raw materials:

(Z,2S,3R,8R,9S)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-((Z)-3-iodoprop-3-enyl)-8-(4-methoxybenzyloxy)-2,3,4,7,8,9-hexahydrooxonine

trimethylsilylacetylene

methyl (+)-(3R,4R)-epoxyhexanoate

(4R,5S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-ethyl-dihydro-furan-2-one