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

Base Information

• Chemical Name: {(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetic acid methyl ester
• CAS No.: 470467-02-8
• Molecular Formula: C₃₈H₆₀O₄Si₂
• Molecular Weight: 637.063

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

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

Chemical Property:

Purity/Quality:

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MSDS Files:

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

There total 11 articles about {(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetic acid methyl ester 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:

triethylsilyl chloride (994-30-9) + {(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-hydroxy-cyclopent-3-enyl}-acetic acid methyl ester (1026808-56-9) → {(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetic acid methyl ester (470467-02-8)

Guidance literature:

With 1H-imidazole;

DOI:10.1016/S0040-4039(02)00786-4

Reference yield:

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4) → {(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-triethylsilanyloxy-cyclopent-3-enyl}-acetic acid methyl ester (470467-02-8)

Guidance literature:

Multi-step reaction with 10 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

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

DOI:10.1021/jo0348571

Reference yield:

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

Guidance literature:

Multi-step reaction with 10 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

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

DOI:10.1021/jo0348571

upstream raw materials:

triethylsilyl chloride

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

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

(4S,1S)-4-[8-{(tert-butyldiphenylsilyl)oxy}octyl]-2-cyclopenten-1-ol

Downstream raw materials:

4-oxo-5α-(2Z)-pentenyl-2-cyclopentene-1α-octanoic acid

13-epi-12-oxo-phytodienoic acid

C₄₀H₆₄O₂Si₂

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

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