(1S,2S)-2-([8-{(tert-butyldiphenylsilyl)oxy}octyl]-4-cyclopentenyl)acetic acid

Base Information

Chemical Name:(1S,2S)-2-([8-{(tert-butyldiphenylsilyl)oxy}octyl]-4-cyclopentenyl)acetic acid
CAS No.:620114-81-0
Molecular Formula:C₃₁H₄₄O₃Si
Molecular Weight:492.774
Hs Code.:

Synonyms:(1S,2S)-2-([8-{(tert-butyldiphenylsilyl)oxy}octyl]-4-cyclopentenyl)acetic acid

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,2S)-2-([8-{(tert-butyldiphenylsilyl)oxy}octyl]-4-cyclopentenyl)acetic acid

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Technology Process of (1S,2S)-2-([8-{(tert-butyldiphenylsilyl)oxy}octyl]-4-cyclopentenyl)acetic acid

There total 6 articles about (1S,2S)-2-([8-{(tert-butyldiphenylsilyl)oxy}octyl]-4-cyclopentenyl)acetic acid 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: 93.0%

: 470467-00-6
(1S,2S)-2-([8-{(tert-butyldiphenylsilyl)oxy}octyl]-4-cyclopentenyl)ethanal

: 620114-81-0
(1S,2S)-2-([8-{(tert-butyldiphenylsilyl)oxy}octyl]-4-cyclopentenyl)acetic acid

Guidance literature:: With chromium(VI) oxide; sulfuric acid; In acetone; for 0.5h; cooling;
DOI:10.1021/jo0348571

Reference yield:

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

: 620114-81-0
(1S,2S)-2-([8-{(tert-butyldiphenylsilyl)oxy}octyl]-4-cyclopentenyl)acetic acid

Guidance literature:: Multi-step reaction with 5 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

With chromium(VI) oxide; Hg(OAc)3; sulfuric acid; tert-butylmagnesium chloride; methyllithium; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 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

: 620114-81-0
(1S,2S)-2-([8-{(tert-butyldiphenylsilyl)oxy}octyl]-4-cyclopentenyl)acetic acid

Guidance literature:: Multi-step reaction with 2 steps

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

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

With chromium(VI) oxide; Hg(OAc)3; sulfuric acid; In acetone; benzene; 1: Claisen rearrangement / 2: Jones oxidation;
DOI:10.1021/jo0348571