(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one

Base Information

Chemical Name:(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one
CAS No.:154815-09-5
Molecular Formula:C₃₁H₃₉NO₅Si
Molecular Weight:533.74
Hs Code.:

Synonyms:(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one

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Chemical Property of (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one

Chemical Property:

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Technology Process of (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one

There total 12 articles about (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one 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: 76.0%

: 154815-08-4
(2R,3R)-3-(benzyloxy)-2-<(Z)-3-(tert-butyldiphenylsilyloxy)-1-propenyl>piperidin-6-one

: (2R,3R)-3-(benzyloxy)-2-<(1R,2S)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one

: 154815-09-5
(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetonitrile; for 14h; Ambient temperature;
DOI:10.1021/jo00085a026

Reference yield:

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

: 154815-09-5
(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one

Guidance literature:: Multi-step reaction with 11 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

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

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 154815-09-5
(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one

Guidance literature:: Multi-step reaction with 2 steps

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

2: 76 percent / N-methylmorpholine N-oxide monohydrate, 4percent aq. OsO₄ / acetonitrile; H₂O / 14 h / Ambient temperature

With 1H-imidazole; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00085a026