{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetaldehyde

Base Information

Chemical Name:{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetaldehyde
CAS No.:470467-03-9
Molecular Formula:C₃₇H₅₈O₃Si₂
Molecular Weight:607.037
Hs Code.:

Synonyms:{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetaldehyde

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Chemical Property of {(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetaldehyde

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Technology Process of {(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetaldehyde

There total 14 articles about {(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetaldehyde 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: 86.0%

: 470467-02-8
{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetic acid methyl ester

: 470467-03-9
{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetaldehyde

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/jo0348571

Reference yield:

: 60410-16-4
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

: 470467-03-9
{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetaldehyde

Guidance literature:: Multi-step reaction with 11 steps

1: 88 percent / CuCN; t-BuMgCl / tetrahydrofuran / 2 h / -18 °C

2: 93 percent / PPh₃; DEAD / toluene / 2 h / -78 - -60 °C

3: 91 percent / MeLi / diethyl ether / 0.67 h / 0 °C

4: 85 percent / Hg(OAc)3 / benzene / 61 h / 170 °C

5: 93 percent / CrO₃; H₂SO₄ / acetone / 0.5 h / cooling

6: 88 percent / I₂; KI; aq. NaHCO₃ / diethyl ether; tetrahydrofuran / 13 h / 20 °C

7: 84 percent / DBU / tetrahydrofuran / 6 h / Heating

8: LiOH*H₂O; H₂O / tetrahydrofuran; methanol / 1 h / 20 °C

9: diethyl ether / 0.5 h / 0 °C

10: 398 mg / imidazole / dimethylformamide / 1 h / 20 °C

11: 86 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

With 1H-imidazole; chromium(VI) oxide; lithium hydroxide; Hg(OAc)3; sulfuric acid; tert-butylmagnesium chloride; water; methyllithium; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; potassium iodide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene; 2: Mitsunobu reaction / 4: Claisen rearrangement / 5: Jones oxidation;
DOI:10.1021/jo0348571

Reference yield:

: 470466-99-0
(4S,1R)-4-[8-{(tert-butyldiphenylsilyl)oxy}octyl]-2-cyclopenten-1-ol

: 470467-03-9
{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent / Hg(OAc)3 / benzene / 61 h / 170 °C

2: 93 percent / CrO₃; H₂SO₄ / acetone / 0.5 h / cooling

3: 88 percent / I₂; KI; aq. NaHCO₃ / diethyl ether; tetrahydrofuran / 13 h / 20 °C

4: 84 percent / DBU / tetrahydrofuran / 6 h / Heating

5: LiOH*H₂O; H₂O / tetrahydrofuran; methanol / 1 h / 20 °C

6: diethyl ether / 0.5 h / 0 °C

7: 398 mg / imidazole / dimethylformamide / 1 h / 20 °C

8: 86 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

With 1H-imidazole; chromium(VI) oxide; lithium hydroxide; Hg(OAc)3; sulfuric acid; water; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene; 1: Claisen rearrangement / 2: Jones oxidation;
DOI:10.1021/jo0348571