(3aS,4S,6S,6aS)-4-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-6-iodo-hexahydro-cyclopenta[b]furan-2-one

Base Information

Chemical Name:(3aS,4S,6S,6aS)-4-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-6-iodo-hexahydro-cyclopenta[b]furan-2-one
CAS No.:620114-82-1
Molecular Formula:C₃₁H₄₃IO₃Si
Molecular Weight:618.671
Hs Code.:

Synonyms:(3aS,4S,6S,6aS)-4-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-6-iodo-hexahydro-cyclopenta[b]furan-2-one

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Chemical Property of (3aS,4S,6S,6aS)-4-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-6-iodo-hexahydro-cyclopenta[b]furan-2-one

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Technology Process of (3aS,4S,6S,6aS)-4-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-6-iodo-hexahydro-cyclopenta[b]furan-2-one

There total 8 articles about (3aS,4S,6S,6aS)-4-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-6-iodo-hexahydro-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: 88.0%

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

: 620114-82-1
(3aS,4S,6S,6aS)-4-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-6-iodo-hexahydro-cyclopenta[b]furan-2-one

Guidance literature:: With iodine; sodium hydrogencarbonate; potassium iodide; In tetrahydrofuran; diethyl ether; at 20 ℃; for 13h;
DOI:10.1021/jo0348571

Reference yield:

: 1259030-59-5
2-((1S,5S)-5-(8-tert-butyldiphenylsilyloxyoctyl)cyclopent-2-enyl)-N,N-dimethyl acetamide

: 620114-82-1
(3aS,4S,6S,6aS)-4-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-6-iodo-hexahydro-cyclopenta[b]furan-2-one

Guidance literature:: With water; iodine; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1039/c0ob00218f

Reference yield:

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

: 620114-82-1
(3aS,4S,6S,6aS)-4-[8-(tert-Butyl-diphenyl-silanyloxy)-octyl]-6-iodo-hexahydro-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 6 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

With chromium(VI) oxide; Hg(OAc)3; sulfuric acid; tert-butylmagnesium chloride; methyllithium; iodine; sodium hydrogencarbonate; triphenylphosphine; potassium iodide; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; acetone; toluene; benzene; 2: Mitsunobu reaction / 4: Claisen rearrangement / 5: Jones oxidation;
DOI:10.1021/jo0348571