(3R,4S,5R)-3,4,5-Trihydroxy-piperidine-1,3-dicarboxylic acid 3-methyl ester 1-phenyl ester

Base Information

Chemical Name:(3R,4S,5R)-3,4,5-Trihydroxy-piperidine-1,3-dicarboxylic acid 3-methyl ester 1-phenyl ester
CAS No.:323201-29-2
Molecular Formula:C₁₄H₁₇NO₇
Molecular Weight:311.291
Hs Code.:

Synonyms:(3R,4S,5R)-3,4,5-Trihydroxy-piperidine-1,3-dicarboxylic acid 3-methyl ester 1-phenyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4S,5R)-3,4,5-Trihydroxy-piperidine-1,3-dicarboxylic acid 3-methyl ester 1-phenyl ester

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Technology Process of (3R,4S,5R)-3,4,5-Trihydroxy-piperidine-1,3-dicarboxylic acid 3-methyl ester 1-phenyl ester

There total 7 articles about (3R,4S,5R)-3,4,5-Trihydroxy-piperidine-1,3-dicarboxylic acid 3-methyl ester 1-phenyl 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: 81.0%

: 323201-33-8
5-hydroxy-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 3-methyl ester 1-phenyl ester

: 323201-29-2
(3R,4S,5R)-3,4,5-Trihydroxy-piperidine-1,3-dicarboxylic acid 3-methyl ester 1-phenyl ester

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone;
DOI:10.1021/ol006810x

Reference yield:

: 93-60-7
methyl 3-pyridinecarboxylate

: 323201-29-2
(3R,4S,5R)-3,4,5-Trihydroxy-piperidine-1,3-dicarboxylic acid 3-methyl ester 1-phenyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / sodium borohydride / methanol / 3 h / -78 °C

2: 92 percent / CH₂Cl₂ / 6 h / -78 - 0 °C

3: 77 percent / TMSOTf; BH₃ / tetrahydrofuran; CH₂Cl₂ / 6 h / -78 - 0 °C

4: 99 percent / Jones reagent / acetone / 0 °C

5: LiAlH₄; (1R,2S)-(-)-N-methylephedrine; 2-ethylaminopyridine / diethyl ether / 3 h / -78 °C

6: 81 percent / OsO₄; NMO

With 2-(ethylamino)pyridine; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; jones reagent; trimethylsilyl trifluoromethanesulfonate; (-)-N-methylephedrine; borane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; 1: Fowler reduction;
DOI:10.1021/ol006810x

Reference yield:

: 1885-14-9
phenyl chloroformate

: 323201-29-2
(3R,4S,5R)-3,4,5-Trihydroxy-piperidine-1,3-dicarboxylic acid 3-methyl ester 1-phenyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / sodium borohydride / methanol / 3 h / -78 °C

2: 92 percent / CH₂Cl₂ / 6 h / -78 - 0 °C

3: 77 percent / TMSOTf; BH₃ / tetrahydrofuran; CH₂Cl₂ / 6 h / -78 - 0 °C

4: 99 percent / Jones reagent / acetone / 0 °C

5: LiAlH₄; (1R,2S)-(-)-N-methylephedrine; 2-ethylaminopyridine / diethyl ether / 3 h / -78 °C

6: 81 percent / OsO₄; NMO

With 2-(ethylamino)pyridine; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; jones reagent; trimethylsilyl trifluoromethanesulfonate; (-)-N-methylephedrine; borane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; 1: Fowler reduction;
DOI:10.1021/ol006810x