(7R,8R,8aS)-8-(benzyloxy)-7-<(3R,5E,7R,8R)-3,6-dimethyl-7,8-O-isopropylidene-5-decen-1-ynyl>-8-methyl-6-oxaoctahydroindolidizine

Base Information

Chemical Name:(7R,8R,8aS)-8-(benzyloxy)-7-<(3R,5E,7R,8R)-3,6-dimethyl-7,8-O-isopropylidene-5-decen-1-ynyl>-8-methyl-6-oxaoctahydroindolidizine
CAS No.:137895-77-3
Molecular Formula:C₂₉H₄₁NO₄
Molecular Weight:467.649
Hs Code.:

Synonyms:(7R,8R,8aS)-8-(benzyloxy)-7-<(3R,5E,7R,8R)-3,6-dimethyl-7,8-O-isopropylidene-5-decen-1-ynyl>-8-methyl-6-oxaoctahydroindolidizine

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Chemical Property of (7R,8R,8aS)-8-(benzyloxy)-7-<(3R,5E,7R,8R)-3,6-dimethyl-7,8-O-isopropylidene-5-decen-1-ynyl>-8-methyl-6-oxaoctahydroindolidizine

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Technology Process of (7R,8R,8aS)-8-(benzyloxy)-7-<(3R,5E,7R,8R)-3,6-dimethyl-7,8-O-isopropylidene-5-decen-1-ynyl>-8-methyl-6-oxaoctahydroindolidizine

There total 11 articles about (7R,8R,8aS)-8-(benzyloxy)-7-<(3R,5E,7R,8R)-3,6-dimethyl-7,8-O-isopropylidene-5-decen-1-ynyl>-8-methyl-6-oxaoctahydroindolidizine 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: 94.0%

: 137895-76-2
(S)-2-<(1R,2R,5R,7E,9R,10R)-1-(benzyloxy)-2-hydroxy-9,10-O-isopropylidene-1,5,8-trimethyl-7-undecen-3-ynyl>-1-(cyanomethyl)pyrrolidine

: 137895-77-3
(7R,8R,8aS)-8-(benzyloxy)-7-<(3R,5E,7R,8R)-3,6-dimethyl-7,8-O-isopropylidene-5-decen-1-ynyl>-8-methyl-6-oxaoctahydroindolidizine

Guidance literature:: With silver trifluoromethanesulfonate; In tetrahydrofuran; at 23 ℃;
DOI:10.1021/ja00027a061

Reference yield:

: 137895-75-1
(4R,5R)-2,2,4-trimethyl-5-((R,E)-5-methylhept-2-en-6-yn-2-yl)-1,3-dioxolane

: 137895-77-3
(7R,8R,8aS)-8-(benzyloxy)-7-<(3R,5E,7R,8R)-3,6-dimethyl-7,8-O-isopropylidene-5-decen-1-ynyl>-8-methyl-6-oxaoctahydroindolidizine

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) THF, hexane, -15 deg C, 15 min, 2.) THF, hexane, -78 deg C, 2.5 h

2: 94 percent / AgOTf / tetrahydrofuran / 3 h / Ambient temperature

With n-butyllithium; silver trifluoromethanesulfonate; In tetrahydrofuran;
DOI:10.1021/ja961640y

Reference yield:

: 19225-74-2
(R)-4,4-Dimethoxy-2-methyl-butyraldehyde

: 137895-77-3
(7R,8R,8aS)-8-(benzyloxy)-7-<(3R,5E,7R,8R)-3,6-dimethyl-7,8-O-isopropylidene-5-decen-1-ynyl>-8-methyl-6-oxaoctahydroindolidizine

Guidance literature:: Multi-step reaction with 9 steps

1: Ph₃P, K₂CO₃ / CH₂Cl₂ / -78 °C

2: 25percent aq. HBF₄ / tetrahydrofuran / 23 °C

3: 100 percent / CH₂Cl₂ / Heating

4: (i-Bu)3Al / pentane; tetrahydrofuran / 23 °C

5: 100 percent / (n-Bu)4NF / tetrahydrofuran / 23 °C

6: TsOH, / 23 °C

7: n-BuLi / tetrahydrofuran / -78 °C

8: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) THF, -78 deg C, 2.5 h

9: 94 percent / AgOSO₂CF₃ / tetrahydrofuran / 23 °C

With tetrafluoroboric acid; n-butyllithium; tetrabutyl ammonium fluoride; triisobutylaluminum; silver trifluoromethanesulfonate; potassium carbonate; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; pentane;
DOI:10.1021/ja00027a061