(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-hydroxy-1,2-(isopropylidenedioxy)propyl>piperidine

Base Information

Chemical Name:(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-hydroxy-1,2-(isopropylidenedioxy)propyl>piperidine
CAS No.:154815-11-9
Molecular Formula:C₁₈H₂₇NO₄
Molecular Weight:321.417
Hs Code.:

Synonyms:(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-hydroxy-1,2-(isopropylidenedioxy)propyl>piperidine

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Chemical Property of (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-hydroxy-1,2-(isopropylidenedioxy)propyl>piperidine

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Technology Process of (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-hydroxy-1,2-(isopropylidenedioxy)propyl>piperidine

There total 13 articles about (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-hydroxy-1,2-(isopropylidenedioxy)propyl>piperidine 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: 71.0%

: 154815-10-8
(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-(isopropylidenedioxy)propyl>piperidin-6-one

: 154815-11-9
(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-hydroxy-1,2-(isopropylidenedioxy)propyl>piperidine

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;
DOI:10.1021/jo00085a026

Reference yield:

: 102794-92-3,145958-02-7,134665-69-3
(2R,4R)-4-formyl-2-phenyl-1,3-dioxane

: 154815-11-9
(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-hydroxy-1,2-(isopropylidenedioxy)propyl>piperidine

Guidance literature:: Multi-step reaction with 13 steps

1: 49 percent / t-BuOK / tetrahydrofuran / 1.) r.t., 20 min, 2.) r.t., 5 min

2: 1.) DIBALH, 2.) I₂ / 1.) CH₂Cl₂, hexane, r.t., 1.5 h, 2.) benzene, irradiation, 30 min

3: 95 percent / pyridine / 1.) 0 deg C, 2 h, 2.) r.t., 2 h

4: 99 percent / dimethylsulfoxide / 1 h / 60 °C

5: 77 percent / 25percent aq. NaOH / methanol / 9 h / Heating

6: 99 percent / diethyl ether / 0.25 h / 0 °C

7: 96 percent / hydroxylamine hydrochloride, KOH / methanol / 1.) 0 deg C, 5 min, 2.) 0 deg C, 30 min

8: 69 percent / NaIO₄ / H₂O / 0.17 h / 0 °C

9: 85 percent / Na₂HPO₄, 5percent sodium amalgam / ethanol / 1 h

10: 90 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

11: 76 percent / N-methylmorpholine N-oxide monohydrate, 4percent aq. OsO₄ / acetonitrile; H₂O / 14 h / Ambient temperature

12: 99 percent / pyridinium p-toluenesulfonate / benzene / 13 h / 55 °C

13: 71 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

With pyridine; 1H-imidazole; potassium hydroxide; sodium hydroxide; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; potassium tert-butylate; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo00085a026

Reference yield:

: 154321-85-4
(E)-(R)-4-(benzyloxy)-N-hydroxy-5,7-octadienamide

: 154815-11-9
(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-hydroxy-1,2-(isopropylidenedioxy)propyl>piperidine

Guidance literature:: Multi-step reaction with 6 steps

1: 69 percent / NaIO₄ / H₂O / 0.17 h / 0 °C

2: 85 percent / Na₂HPO₄, 5percent sodium amalgam / ethanol / 1 h

3: 90 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

4: 76 percent / N-methylmorpholine N-oxide monohydrate, 4percent aq. OsO₄ / acetonitrile; H₂O / 14 h / Ambient temperature

5: 99 percent / pyridinium p-toluenesulfonate / benzene / 13 h / 55 °C

6: 71 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

With 1H-imidazole; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo00085a026