2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-4-hydroxycyclopentanone

Base Information

Chemical Name:2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-4-hydroxycyclopentanone
CAS No.:911218-22-9
Molecular Formula:C₃₂H₄₀O₄Si
Molecular Weight:516.753
Hs Code.:

Synonyms:2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-4-hydroxycyclopentanone

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Chemical Property of 2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-4-hydroxycyclopentanone

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Technology Process of 2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-4-hydroxycyclopentanone

There total 11 articles about 2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-4-hydroxycyclopentanone 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: 74.0%

: 3-benzyloxymethyl-4-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-6-oxabicyclo[3.1.0]hexan-2-one

: 911218-22-9
2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-4-hydroxycyclopentanone

Guidance literature:: With sodium tetrahydroborate; ethanol; diphenyl diselenide; In acetic acid; at 0 ℃; for 0.0833333h;
DOI:10.1021/ol0615230

Reference yield:

: 911218-16-1
2-benzyloxymethyl-cyclopent-2-enone

: 911218-22-9
2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-4-hydroxycyclopentanone

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

1.2: 72 percent / tetrahydrofuran; hexane / 0.75 h / -78 °C

2.1: O₃ / CH₂Cl₂; methanol / -78 °C

2.2: 96 percent / NaBH₄ / CH₂Cl₂; methanol / -78 - 0 °C

3.1: 86 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

4.1: 94 percent / PCC / CH₂Cl₂ / 20 °C

5.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.25 h / -78 °C

5.2: ClSiMe₃ / tetrahydrofuran; hexane / 0.25 h / -78 °C

5.3: 51 percent / Pd(OAc)2 / acetonitrile / 2.5 h / 0 - 20 °C

6.1: 80 percent / aq. H₂O₂; aq. KOH / methanol / 2 h / -10 °C

7.1: 74 percent / PhSeSePh; NaBH₄; EtOH / acetic acid / 0.08 h / 0 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; ethanol; diphenyl diselenide; dihydrogen peroxide; ozone; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid;
DOI:10.1021/ol0615230

Reference yield:

: 911218-25-2
2-benzyloxymethyl-3-(2-hydroxy-1-methyl-ethyl)-cyclopentanol

: 911218-22-9
2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-4-hydroxycyclopentanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

2.1: 94 percent / PCC / CH₂Cl₂ / 20 °C

3.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: ClSiMe₃ / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.3: 51 percent / Pd(OAc)2 / acetonitrile / 2.5 h / 0 - 20 °C

4.1: 80 percent / aq. H₂O₂; aq. KOH / methanol / 2 h / -10 °C

5.1: 74 percent / PhSeSePh; NaBH₄; EtOH / acetic acid / 0.08 h / 0 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; ethanol; diphenyl diselenide; dihydrogen peroxide; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid;
DOI:10.1021/ol0615230