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

Base Information

• Chemical Name: (Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine
• CAS No.: 140170-15-6
• Molecular Formula: C₂₇H₃₈O₄Si
• Molecular Weight: 454.682

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

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

There total 33 articles about (Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-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: 83.0%

(Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-8-dimethylsilanyloxy-2-ethyl-9-methylene-2,3,4,7,8,9-hexahydrooxonine (140170-11-2) → (Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine (140170-15-6) + (Z,2R,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine (140225-14-5)

Guidance literature:

(Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-8-dimethylsilanyloxy-2-ethyl-9-methylene-2,3,4,7,8,9-hexahydrooxonine; With Wilkinson's catalyst; triphenylphosphine; In tetrahydrofuran; for 16h; Reflux;

With potassium hydroxide; water; dihydrogen peroxide; In tetrahydrofuran; methanol; at 20 ℃; for 1.5h; diastereoselective reaction;

DOI:10.1002/chem.200701567

Reference yield: 80.0%

(Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-8-dimethylsilanyloxy-2-ethyl-9-methylene-2,3,4,7,8,9-hexahydrooxonine (140170-11-2) → (Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine (140170-15-6)

Guidance literature:

(Z,2S,3R,8R)-3-tert-butyldiphenylsilanyloxy-8-dimethylsilanyloxy-2-ethyl-9-methylene-2,3,4,7,8,9-hexahydrooxonine; Wilkinson's catalyst; In tetrahydrofuran; Heating;

With potassium hydroxide; dihydrogen peroxide; In tetrahydrofuran; methanol;

DOI:10.1055/s-2005-918470

Reference yield:

methyl (+)-(3R,4R)-epoxyhexanoate (876064-66-3) → (Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine (140170-15-6)

Guidance literature:

Multi-step reaction with 13 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

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

DOI:10.1055/s-2005-918470

upstream raw materials:

(Z)-(2S,3R,8R)-3-(tert-Butyl-diphenyl-silanyloxy)-8-diisopropylsilanyloxy-2-ethyl-9-methylene-2,3,4,7,8,9-hexahydro-oxonine

(Z)-(2S,3R,8R)-3-(tert-Butyl-diphenyl-silanyloxy)-8-dimethylsilanyloxy-2-ethyl-9-methylene-2,3,4,7,8,9-hexahydro-oxonine

(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-2-methylene-2,3,4,7,8,9-hexahydrooxonine

Downstream raw materials:

[(Z)-(2S,3R,8R,9S)-3-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-methanol

(Z,2S,4aS,6S,7R,11aR)-7-tert-butyldiphenylsilanyloxy-6-ethyl-2-(4-methoxyphenyl)-4a,6,7,8,11,11a-hexahydro-4H-1,3,5-trioxabenzocyclononene

(Z,2S,3R,8R,9S)-2-ethyl-3-hydroxy-8-(4-methoxybenzyloxy)-9-((Z)-pent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine

(Z,2S,3S,8R,9S)-3-bromo-2-ethyl-8-(4-methoxybenzyloxy)-9-((Z)-pent-2-en-4-ynyl)-2,3,4,7,8,9-hexahydrooxonine

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 140170-15-6 (Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-3-hydroxy-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonine

Send

Send

Metric Ton KG G Pound L ML

Send

Send