2,2,2-trichloroethyl 6β-<3-(benzyloxy)prop-1-yl>-1β-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylate

Base Information

Chemical Name:2,2,2-trichloroethyl 6β-<3-(benzyloxy)prop-1-yl>-1β-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylate
CAS No.:83220-55-7
Molecular Formula:C₂₉H₄₁Cl₃O₄Si
Molecular Weight:588.087
Hs Code.:

Synonyms:2,2,2-trichloroethyl 6β-<3-(benzyloxy)prop-1-yl>-1β-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylate

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Chemical Property of 2,2,2-trichloroethyl 6β-<3-(benzyloxy)prop-1-yl>-1β-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylate

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Technology Process of 2,2,2-trichloroethyl 6β-<3-(benzyloxy)prop-1-yl>-1β-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylate

There total 6 articles about 2,2,2-trichloroethyl 6β-<3-(benzyloxy)prop-1-yl>-1β-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylate 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: 61.0%

: 83220-53-5
2,2,2-trichloroethyl (E,E)-14-(benzyloxy)-7-<(tert-butyldimethylsilyl)oxy>-8,10-tetradecadien-2-ynoate

: 83220-56-8
2,2,2-trichloroethyl 6β-<3-(benzyloxy)prop-1-yl>-1α-hydroxy-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylate

: 83220-55-7
2,2,2-trichloroethyl 6β-<3-(benzyloxy)prop-1-yl>-1β-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylate

Guidance literature:: With hydrogenchloride; Yield given. Multistep reaction; 1.) toluene, 160 deg C, 61 h, 2.) THF, MeOH, 10 deg C, 3.) 23 deg C, 10 h;
DOI:10.1021/jo00145a002

Reference yield:

: 5470-84-8
4-benzyloxybutanal

: 83220-55-7
2,2,2-trichloroethyl 6β-<3-(benzyloxy)prop-1-yl>-1β-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

2: tetrahydrofuran / 0.5 h / 0 - 23 °C

3: KF / dimethylformamide; H₂O / 39 h / 23 °C

4: 98 percent Chromat_. / imidazole / tetrahydrofuran / 53 h / 23 °C

5: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) from -78 deg C to 0 deg C, 55 min

6: 2.) aq HCl / 1.) toluene, 160 deg C, 61 h, 2.) THF, MeOH, 10 deg C, 3.) 23 deg C, 10 h

With 1H-imidazole; hydrogenchloride; potassium fluoride; n-butyllithium; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00145a002

Reference yield:

: 83220-50-2
(E,E)-8-(benzyloxy)-2,4-octadienal

: 83220-55-7
2,2,2-trichloroethyl 6β-<3-(benzyloxy)prop-1-yl>-1β-<(tert-butyldimethylsilyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: tetrahydrofuran / 0.5 h / 0 - 23 °C

2: KF / dimethylformamide; H₂O / 39 h / 23 °C

3: 98 percent Chromat_. / imidazole / tetrahydrofuran / 53 h / 23 °C

4: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) from -78 deg C to 0 deg C, 55 min

5: 2.) aq HCl / 1.) toluene, 160 deg C, 61 h, 2.) THF, MeOH, 10 deg C, 3.) 23 deg C, 10 h

With 1H-imidazole; hydrogenchloride; potassium fluoride; n-butyllithium; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00145a002