(3S,5S)-3,5-di-O-benzylquinuclidine-3,5-diol

Base Information

Chemical Name:(3S,5S)-3,5-di-O-benzylquinuclidine-3,5-diol
CAS No.:162601-59-4
Molecular Formula:C₂₁H₂₅NO₂
Molecular Weight:323.435
Hs Code.:

Synonyms:(3S,5S)-3,5-di-O-benzylquinuclidine-3,5-diol

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Chemical Property of (3S,5S)-3,5-di-O-benzylquinuclidine-3,5-diol

Chemical Property:

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Technology Process of (3S,5S)-3,5-di-O-benzylquinuclidine-3,5-diol

There total 20 articles about (3S,5S)-3,5-di-O-benzylquinuclidine-3,5-diol 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: 78.0%

: Methanesulfonic acid (S)-2-benzyloxy-2-((3S,4S)-3-benzyloxy-piperidin-4-yl)-ethyl ester

: 162601-59-4
(3S,5S)-3,5-di-O-benzylquinuclidine-3,5-diol

Guidance literature:: With sodium acetate; In ethanol; at 60 ℃; for 4h;
DOI:10.1016/0040-4020(94)01009-O

Reference yield:

: 1941-50-0
D-arabinose diethyl dithioacetal

: 162601-59-4
(3S,5S)-3,5-di-O-benzylquinuclidine-3,5-diol

Guidance literature:: Multi-step reaction with 20 steps

1: 95 percent / imidazole / dimethylformamide / 0 °C

2: 1.) HgO, HgCl₂; 2.) CuSO₄, dl-camphorsulfonic acid / 1.) aq. acetone, 6 h; 2.) acetone, RT, 4 h

3: pyridinium perchlorate, 3A molecular sieve / CH₂Cl₂ / 4 h / Ambient temperature

4: benzene / 4 h / Heating

5: H₂ / 10percent Pd/C / ethyl acetate / 48 h / Ambient temperature

6: 88 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

7: 98 percent / pyridine / 3 h / 0 °C

8: 96 percent / NaN₃ / dimethylformamide / 6 h / 50 °C

9: 95 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

10: 94 percent / pyridine / 3 h / 0 °C

11: H₂ / Pd black / ethanol / Ambient temperature

12: NaOAc / ethanol / 10 h / Heating

13: aq. NaHCO₃ / ethyl acetate / 0 °C

14: 89 percent / H₂O; trifluoroacetic acid / 4 h / 0 °C

15: 70 percent / NaH, Bu₄NI / tetrahydrofuran / 24 h

16: HgO, HgCl₂ / acetone; H₂O / 1 h / Ambient temperature

17: 88 percent / NaBH₄ / ethanol / 4 h / Ambient temperature

18: 99 percent / pyridine / 2 h / 0 °C

19: H₂ / 10percent Pd/C / ethanol / 24 h

20: 78 percent / NaOAc / ethanol / 4 h / 60 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; 3 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; pyridinium perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; copper(II) sulfate; mercury dichloride; mercury(II) oxide; palladium on activated charcoal; palladium; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; trifluoroacetic acid; benzene;
DOI:10.1016/0040-4020(94)01009-O

Reference yield:

: Methanesulfonic acid (3aS,5S,6S,6aS)-6-(2-amino-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

: 162601-59-4
(3S,5S)-3,5-di-O-benzylquinuclidine-3,5-diol

Guidance literature:: Multi-step reaction with 9 steps

1: NaOAc / ethanol / 10 h / Heating

2: aq. NaHCO₃ / ethyl acetate / 0 °C

3: 89 percent / H₂O; trifluoroacetic acid / 4 h / 0 °C

4: 70 percent / NaH, Bu₄NI / tetrahydrofuran / 24 h

5: HgO, HgCl₂ / acetone; H₂O / 1 h / Ambient temperature

6: 88 percent / NaBH₄ / ethanol / 4 h / Ambient temperature

7: 99 percent / pyridine / 2 h / 0 °C

8: H₂ / 10percent Pd/C / ethanol / 24 h

9: 78 percent / NaOAc / ethanol / 4 h / 60 °C

With sodium tetrahydroborate; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; mercury dichloride; mercury(II) oxide; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; water; ethyl acetate; acetone; trifluoroacetic acid;
DOI:10.1016/0040-4020(94)01009-O