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

Base Information

Chemical Name:{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-hydroxy-cyclopent-3-enyl}-acetic acid methyl ester
CAS No.:1026808-56-9
Molecular Formula:C₃₂H₄₆O₄Si
Molecular Weight:522.8
Hs Code.:

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

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

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

There total 10 articles about {(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-hydroxy-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:

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

: 1026808-56-9
{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-hydroxy-cyclopent-3-enyl}-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 9 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

With 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; 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

: 1026808-56-9
{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-hydroxy-cyclopent-3-enyl}-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 470466-96-7
(4S,1S)-4-[8-{(tert-butyldiphenylsilyl)oxy}octyl]-2-cyclopenten-1-ol

: 1026808-56-9
{(1S,2S,5R)-2-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-5-hydroxy-cyclopent-3-enyl}-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / PPh₃; DEAD / toluene / 2 h / -78 - -60 °C

2: 91 percent / MeLi / diethyl ether / 0.67 h / 0 °C

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

4: 93 percent / CrO₃; H₂SO₄ / acetone / 0.5 h / cooling

5: 88 percent / I₂; KI; aq. NaHCO₃ / diethyl ether; tetrahydrofuran / 13 h / 20 °C

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

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

8: diethyl ether / 0.5 h / 0 °C

With chromium(VI) oxide; lithium hydroxide; Hg(OAc)3; sulfuric acid; water; methyllithium; iodine; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; potassium iodide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; acetone; toluene; benzene; 1: Mitsunobu reaction / 3: Claisen rearrangement / 4: Jones oxidation;
DOI:10.1021/jo0348571