4-[8-(tert-butyl-diphenyl-silanyloxy)-octyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

Base Information

Chemical Name:4-[8-(tert-butyl-diphenyl-silanyloxy)-octyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one
CAS No.:470467-06-2
Molecular Formula:C₃₁H₄₂O₃Si
Molecular Weight:490.758
Hs Code.:

4-[8-(<i>tert</i>-butyl-diphenyl-silanyloxy)-octyl]-3,3a,4,6a-tetrahydro-cyclopenta[<i>b</i>]furan-2-one

Synonyms:4-[8-(tert-butyl-diphenyl-silanyloxy)-octyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

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Chemical Property of 4-[8-(tert-butyl-diphenyl-silanyloxy)-octyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

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Technology Process of 4-[8-(tert-butyl-diphenyl-silanyloxy)-octyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

There total 6 articles about 4-[8-(tert-butyl-diphenyl-silanyloxy)-octyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 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: 76.0%

: 620114-86-5
(3aR,4S,6R,6aR)-4-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-6-iodo-hexahydro-cyclopenta[b]furan-2-one

: 470467-06-2
4-[8-(tert-butyl-diphenyl-silanyloxy)-octyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 6h; Heating;
DOI:10.1021/jo0348571

Reference yield: 36.0%

: 470467-05-1
(1R,2S)-2-([8-{(tert-butyldiphenylsilyl)oxy}octyl]-4-cyclopentenyl)ethanal

: 470467-06-2
4-[8-(tert-butyl-diphenyl-silanyloxy)-octyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

Guidance literature:: (1R,2S)-2-([8-{(tert-butyldiphenylsilyl)oxy}octyl]-4-cyclopentenyl)ethanal; With chromium(VI) oxide; sulfuric acid; In acetone;

With iodine; sodium hydrogencarbonate; potassium iodide; In water; at 20 ℃; for 17h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;
DOI:10.1016/S0040-4039(02)00786-4

Reference yield:

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

: 470467-06-2
4-[8-(tert-butyl-diphenyl-silanyloxy)-octyl]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 5 steps

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

2: 79 percent / Hg(OAc)3 / benzene / 64 h / 170 °C

3: CrO₃; H₂SO₄ / acetone / 0.5 h / cooling

4: 693 mg / I₂; KI; aq. NaHCO₃ / diethyl ether; tetrahydrofuran / 17 h / 20 °C

5: 76 percent / DBU / tetrahydrofuran / 6 h / Heating

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