(2S,3R)-3-Benzyloxy-2-(3-hydroxy-2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,3R)-3-Benzyloxy-2-(3-hydroxy-2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester
CAS No.:223676-16-2
Molecular Formula:C₂₀H₂₉NO₅
Molecular Weight:363.454
Hs Code.:

Synonyms:(2S,3R)-3-Benzyloxy-2-(3-hydroxy-2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,3R)-3-Benzyloxy-2-(3-hydroxy-2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,3R)-3-Benzyloxy-2-(3-hydroxy-2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester

There total 20 articles about (2S,3R)-3-Benzyloxy-2-(3-hydroxy-2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester 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%

: 24424-99-5
di-tert-butyl dicarbonate

: 249737-32-4
(2S',3R')-1-[2'-(3'-benzyloxy)piperidino]-3-hydroxy-2-propanone

: 223676-16-2
(2S,3R)-3-Benzyloxy-2-(3-hydroxy-2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: In dichloromethane; at 0 ℃; for 3h;
DOI:10.1021/jo990877k

Reference yield: 32.0%

: (2S,3R)-3-Benzyloxy-2-(2-trimethylsilanyloxy-allyl)-piperidine-1-carboxylic acid tert-butyl ester

: 223676-16-2
(2S,3R)-3-Benzyloxy-2-(3-hydroxy-2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/jo990877k

Reference yield:

: 52813-63-5
(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

: 223676-16-2
(2S,3R)-3-Benzyloxy-2-(3-hydroxy-2-oxo-propyl)-piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 98 percent

2: LiBH₄ / tetrahydrofuran

3: 80 percent / imidazole

4: NaH / tetrahydrofuran / 20 °C

5: 64 percent / HCO₂H / diethyl ether

6: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7: Yb(OTf)3 / H₂O; tetrahydrofuran / 0.75 h / 0 °C

8: 99 percent / HF / tetrahydrofuran; H₂O

9: 96 percent / PPh₃; CBr₄ / CH₂Cl₂

10: 70 percent / CAN / acetonitrile; H₂O / 2 h / 0 °C

11: CH₂Cl₂ / 3 h / 0 °C

12: LHMDS / tetrahydrofuran / 1 h / -78 °C

13: 32 percent / MCPBA / CH₂Cl₂ / -78 - 20 °C

With 1H-imidazole; lithium borohydride; formic acid; oxalyl dichloride; ammonium cerium(IV) nitrate; carbon tetrabromide; hydrogen fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; 1: Substitution / 2: Reduction / 3: Substitution / 4: Substitution / 5: Substitution / 6: Oxidation / 7: Condensation / 8: Hydrolysis / 9: Cyclization / 10: Substitution / 11: Substitution / 12: Substitution / 13: Oxidation;
DOI:10.1021/jo990877k