(3R,4S,5S,6R)-5-Benzyloxymethyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-6-methyl-piperidine-3,4-diol

Base Information

Chemical Name:(3R,4S,5S,6R)-5-Benzyloxymethyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-6-methyl-piperidine-3,4-diol
CAS No.:727975-29-3
Molecular Formula:C₂₂H₂₉NO₄
Molecular Weight:371.477
Hs Code.:

Synonyms:(3R,4S,5S,6R)-5-Benzyloxymethyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-6-methyl-piperidine-3,4-diol

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Chemical Property of (3R,4S,5S,6R)-5-Benzyloxymethyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-6-methyl-piperidine-3,4-diol

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Technology Process of (3R,4S,5S,6R)-5-Benzyloxymethyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-6-methyl-piperidine-3,4-diol

There total 5 articles about (3R,4S,5S,6R)-5-Benzyloxymethyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-6-methyl-piperidine-3,4-diol 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: 32.0%

: 727975-25-9
(3R,6S,7S,8S,8aS)-8-Benzyloxymethyl-6,7-dihydroxy-8a-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

: 727975-29-3
(3R,4S,5S,6R)-5-Benzyloxymethyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-6-methyl-piperidine-3,4-diol

: (3R,4S,5S,6S)-5-Benzyloxymethyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-6-methyl-piperidine-3,4-diol

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 24h;
DOI:10.1016/j.tetlet.2004.04.121

Reference yield:

: 100-39-0
benzyl bromide

: 727975-29-3
(3R,4S,5S,6R)-5-Benzyloxymethyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-6-methyl-piperidine-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: LiAlH₄; 8aS-Me-5-oxo-3R-Ph-hexahydro-oxazolo[3,2-a]pyridine-8S-COOMe / tetrahydrofuran / 5 h / 0 - 20 °C

1.2: 30 percent / NaH / tetrahydrofuran / 24 h / 0 °C

2.1: LiHMDS; PhSeBr / tetrahydrofuran / -78 °C

2.2: 31 percent / mCPBA / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 79 percent / OsO₄; Ba(ClO₃)2 / tetrahydrofuran; H₂O / 96 h

4.1: 32 percent / BH₃*DMS / tetrahydrofuran / 24 h / 0 - 20 °C

With osmium(VIII) oxide; lithium aluminium tetrahydride; barium chlorate; dimethylsulfide borane complex; 8aS-Me-5-oxo-3R-Ph-hexahydro-oxazolo[3,2-a]pyridine-8S-COOMe; Phenylselenyl bromide; lithium hexamethyldisilazane; In tetrahydrofuran; water;
DOI:10.1016/j.tetlet.2004.04.121

Reference yield:

: (3R,8R,8aS)-8a-Methyl-5-oxo-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-8-carboxylic acid methyl ester

: 727975-29-3
(3R,4S,5S,6R)-5-Benzyloxymethyl-1-((R)-2-hydroxy-1-phenyl-ethyl)-6-methyl-piperidine-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: LiAlH₄; 8aS-Me-5-oxo-3R-Ph-hexahydro-oxazolo[3,2-a]pyridine-8S-COOMe / tetrahydrofuran / 5 h / 0 - 20 °C

1.2: 30 percent / NaH / tetrahydrofuran / 24 h / 0 °C

2.1: LiHMDS; PhSeBr / tetrahydrofuran / -78 °C

2.2: 31 percent / mCPBA / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 79 percent / OsO₄; Ba(ClO₃)2 / tetrahydrofuran; H₂O / 96 h

4.1: 32 percent / BH₃*DMS / tetrahydrofuran / 24 h / 0 - 20 °C

With osmium(VIII) oxide; lithium aluminium tetrahydride; barium chlorate; dimethylsulfide borane complex; 8aS-Me-5-oxo-3R-Ph-hexahydro-oxazolo[3,2-a]pyridine-8S-COOMe; Phenylselenyl bromide; lithium hexamethyldisilazane; In tetrahydrofuran; water;
DOI:10.1016/j.tetlet.2004.04.121