(Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-methylene-8-trimethylsilanyloxy-2,3,4,7,8,9-hexahydrooxonine

Base Information

• Chemical Name: (Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-methylene-8-trimethylsilanyloxy-2,3,4,7,8,9-hexahydrooxonine
• CAS No.: 140170-21-4
• Molecular Formula: C₃₀H₄₄O₃Si₂
• Molecular Weight: 508.849
• Mol file: 140170-21-4.mol

Synonyms:(Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-methylene-8-trimethylsilanyloxy-2,3,4,7,8,9-hexahydrooxonine

Chemical Property of (Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-methylene-8-trimethylsilanyloxy-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)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-methylene-8-trimethylsilanyloxy-2,3,4,7,8,9-hexahydrooxonine

There total 15 articles about (Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-methylene-8-trimethylsilanyloxy-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: 90.0%

(Z,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-trimethylsilanyloxy-4,7,8,9-tetrahydro-3H-oxonin-2-one (140170-20-3) → (Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-methylene-8-trimethylsilanyloxy-2,3,4,7,8,9-hexahydrooxonine (140170-21-4)

Guidance literature:

With dmap; In tetrahydrofuran; at -40 - 20 ℃;

DOI:10.1055/s-2005-918470

Reference yield: 80.0%

(Z,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-trimethylsilanyloxy-4,7,8,9-tetrahydro-3H-oxonin-2-one (140170-20-3) + Tebbe's reagent → (Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-methylene-8-trimethylsilanyloxy-2,3,4,7,8,9-hexahydrooxonine (140170-21-4)

Guidance literature:

With dmap; In tetrahydrofuran; toluene; at -40 - 20 ℃;

DOI:10.1002/chem.200701567

Reference yield:

methyl (+)-(3R,4R)-epoxyhexanoate (876064-66-3) → (Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-2-ethyl-9-methylene-8-trimethylsilanyloxy-2,3,4,7,8,9-hexahydrooxonine (140170-21-4)

Guidance literature:

Multi-step reaction with 10 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

With 1H-imidazole; dmap; sodium periodate; sulfuric acid; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 7.1: Claisen rearrangement;

DOI:10.1055/s-2005-918470

upstream raw materials:

(Z)-(3R,8R,9S)-8-(tert-Butyl-diphenyl-silanyloxy)-9-ethyl-3-trimethylsilanyloxy-4,7,8,9-tetrahydro-3H-oxonin-2-one

(Z)-(8R,9S)-8-(tert-Butyl-diphenyl-silanyloxy)-9-ethyl-4,7,8,9-tetrahydro-3H-oxonin-2-one

(Z,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-4,7,8,9-tetrahydro-3H-oxonin-2-one

(Z,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-trimethylsilanyloxy-4,7,8,9-tetrahydro-3H-oxonin-2-one

Downstream raw materials:

(+)-obtusenyne

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

(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

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