(αR,2S,3R,6S,8S)-8-<2-(benzyloxy)ethyl>-α,3-dimethyl-1,7-dioxaspiro<5.5>undecane-2-ethanal

Base Information

Chemical Name:(αR,2S,3R,6S,8S)-8-<2-(benzyloxy)ethyl>-α,3-dimethyl-1,7-dioxaspiro<5.5>undecane-2-ethanal
CAS No.:142592-57-2
Molecular Formula:C₂₂H₃₂O₄
Molecular Weight:360.494
Hs Code.:

Synonyms:

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Chemical Property of (αR,2S,3R,6S,8S)-8-<2-(benzyloxy)ethyl>-α,3-dimethyl-1,7-dioxaspiro<5.5>undecane-2-ethanal

Chemical Property:

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Technology Process of (αR,2S,3R,6S,8S)-8-<2-(benzyloxy)ethyl>-α,3-dimethyl-1,7-dioxaspiro<5.5>undecane-2-ethanal

There total 21 articles about (αR,2S,3R,6S,8S)-8-<2-(benzyloxy)ethyl>-α,3-dimethyl-1,7-dioxaspiro<5.5>undecane-2-ethanal 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:

: 91285-62-0,111322-01-1,119239-98-4
(S)-1-(benzyloxy)-3-hydroxyhex-5-ene

: 142592-57-2
(αR,2S,3R,6S,8S)-8-<2-(benzyloxy)ethyl>-α,3-dimethyl-1,7-dioxaspiro<5.5>undecane-2-ethanal

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 3N aq. NaOH, 30percent H₂O₂ / 1.) THF, 65 deg C, 3 h, 2.) 1 h, r.t.

2: 97 percent / camphorsulphonic acid / CH₂Cl₂ / 1 h / Ambient temperature

3: 80 percent / H₂ / 10percent Pd/C / ethanol / 12 h / Ambient temperature

4: 88 percent / camphorsulphonic acid, CuSO₄ / acetone / 10 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 1 h

6: NaI / acetone / 3 h / 40 °C

8: 76 percent / NaH / paraffin; tetrahydrofuran / 3 h / Ambient temperature

9: 71 percent / n-Bu₄NF / tetrahydrofuran / 8 h / Ambient temperature

10: 1.) 4-methylmorpholine-N-oxide (NMO), 4 Angstroem molecular sieves, 2.) tetra-n-propylammonium perruthenate (TPAP) / 1.) CH₂Cl₂, 10 min, r.t., 2.) 1 h

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydride; copper(II) sulfate; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetone; paraffin;
DOI:10.1016/S0040-4020(01)80467-1

Reference yield:

: 144604-65-9
(S)-methyl-7-(benzyloxy)-5-hydroxy-2-heptenoate

: 142592-57-2
(αR,2S,3R,6S,8S)-8-<2-(benzyloxy)ethyl>-α,3-dimethyl-1,7-dioxaspiro<5.5>undecane-2-ethanal

Guidance literature:: Multi-step reaction with 3 steps

1: H₂ / PtO₂/C / CH₂Cl₂ / 4 h / Ambient temperature

3: 1.) 4-methylmorpholine-N-oxide (NMO), 4 Angstroem molecular sieves, 2.) tetra-n-propylammonium perruthenate (TPAP) / 1.) CH₂Cl₂, 10 min, r.t., 2.) 1 h

With tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; 4-methylmorpholine N-oxide; PtO₂/C; In dichloromethane;
DOI:10.1016/S0040-4020(01)80467-1

Reference yield:

: 142592-73-2
(S)-6-(benzyloxy)-1,4-hexanediol

: 142592-57-2
(αR,2S,3R,6S,8S)-8-<2-(benzyloxy)ethyl>-α,3-dimethyl-1,7-dioxaspiro<5.5>undecane-2-ethanal

Guidance literature:: Multi-step reaction with 9 steps

1: 97 percent / camphorsulphonic acid / CH₂Cl₂ / 1 h / Ambient temperature

2: 80 percent / H₂ / 10percent Pd/C / ethanol / 12 h / Ambient temperature

3: 88 percent / camphorsulphonic acid, CuSO₄ / acetone / 10 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 1 h

5: NaI / acetone / 3 h / 40 °C

7: 76 percent / NaH / paraffin; tetrahydrofuran / 3 h / Ambient temperature

8: 71 percent / n-Bu₄NF / tetrahydrofuran / 8 h / Ambient temperature

9: 1.) 4-methylmorpholine-N-oxide (NMO), 4 Angstroem molecular sieves, 2.) tetra-n-propylammonium perruthenate (TPAP) / 1.) CH₂Cl₂, 10 min, r.t., 2.) 1 h

With tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; copper(II) sulfate; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetone; paraffin;
DOI:10.1016/S0040-4020(01)80467-1