(2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide

Base Information

Chemical Name:(2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide
CAS No.:216860-70-7
Molecular Formula:C₁₅H₁₉NO₅S
Molecular Weight:325.386
Hs Code.:

Synonyms:(2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide

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Chemical Property of (2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide

Chemical Property:

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Technology Process of (2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide

There total 7 articles about (2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide 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: 92.0%

: 216860-69-4
(4R,5R)-5-[(phenylsulfonyl)amino]-4-(2-carboxyethyl)-2,2-dimethyl-1,3-dioxane

: 216860-70-7
(2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 12h;
DOI:10.1021/jo980592s

Reference yield:

: 103197-51-9
N-(Phenylsulfonyl)-D-serine

: 216860-70-7
(2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1.92 h / -75 - 0 °C

1.2: 93 percent / tetrahydrofuran; hexane; diethyl ether / 20 h / 0 - 20 °C

2.1: 84 percent / L-Selectride / tetrahydrofuran / 2.25 h / -78 - -73 °C

3.1: 80 percent / p-toluenesulfonic acid / tetrahydrofuran / 48 h / 20 °C

4.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

4.2: 81 percent / NaOH; H₂O₂ / tetrahydrofuran; ethanol; H₂O / 0 - 20 °C / Heating

5.1: 75 percent / NaIO₄ / RuCl₃*3H₂O / acetonitrile; CCl₄; aq. phosphate buffer / 90 h / 20 °C / pH 7.0

6.1: 92 percent / 4-(dimethylamino)pyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 12 h / 0 °C

With dmap; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; L-Selectride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; phosphate buffer; hexane; dichloromethane; acetonitrile; 1.1: Metallation / 1.2: Grignard reaction / 2.1: Reduction / 3.1: Cyclization / 4.1: Addition / 4.2: Oxidation / 5.1: Oxidation / 6.1: Cyclization;
DOI:10.1021/jo980592s

Reference yield:

: 150989-66-5
(4R,5R)-4-Allyl-2,2-dimethyl-5-<(phenylsulfonyl)amino>-1,3-dioxane

: 216860-70-7
(2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

1.2: 81 percent / NaOH; H₂O₂ / tetrahydrofuran; ethanol; H₂O / 0 - 20 °C / Heating

2.1: 75 percent / NaIO₄ / RuCl₃*3H₂O / acetonitrile; CCl₄; aq. phosphate buffer / 90 h / 20 °C / pH 7.0

3.1: 92 percent / 4-(dimethylamino)pyridine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 12 h / 0 °C

With dmap; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; phosphate buffer; dichloromethane; acetonitrile; 1.1: Addition / 1.2: Oxidation / 2.1: Oxidation / 3.1: Cyclization;
DOI:10.1021/jo980592s