(2S,3R,4R,5S)-1-Benzyl-4-benzyloxy-2-(2-hydroxy-ethyl)-piperidine-3,5-diol

Base Information

Chemical Name:(2S,3R,4R,5S)-1-Benzyl-4-benzyloxy-2-(2-hydroxy-ethyl)-piperidine-3,5-diol
CAS No.:247144-50-9
Molecular Formula:C₂₁H₂₇NO₄
Molecular Weight:357.45
Hs Code.:

Synonyms:(2S,3R,4R,5S)-1-Benzyl-4-benzyloxy-2-(2-hydroxy-ethyl)-piperidine-3,5-diol

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Chemical Property of (2S,3R,4R,5S)-1-Benzyl-4-benzyloxy-2-(2-hydroxy-ethyl)-piperidine-3,5-diol

Chemical Property:

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Technology Process of (2S,3R,4R,5S)-1-Benzyl-4-benzyloxy-2-(2-hydroxy-ethyl)-piperidine-3,5-diol

There total 6 articles about (2S,3R,4R,5S)-1-Benzyl-4-benzyloxy-2-(2-hydroxy-ethyl)-piperidine-3,5-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: 84.0%

: 247144-49-6
(3aS,6S,7R,7aR)-4-Benzyl-7-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]pyridin-2-one

: 247144-50-9
(2S,3R,4R,5S)-1-Benzyl-4-benzyloxy-2-(2-hydroxy-ethyl)-piperidine-3,5-diol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 2h;
DOI:10.1039/a905440e

Reference yield:

: 23558-05-6
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

: 247144-50-9
(2S,3R,4R,5S)-1-Benzyl-4-benzyloxy-2-(2-hydroxy-ethyl)-piperidine-3,5-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 24 percent / acetonitrile / 2 h / Heating

2.1: TFA; H₂O / 20 °C

3.1: AcOH / methanol / 2 h / -78 °C

3.2: 79 percent / NaCNBH₃; AcOH / methanol / 24 h / 20 °C

4.1: 84 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

With lithium aluminium tetrahydride; water; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; acetonitrile; 1.1: Condensation / 2.1: Ring cleavage / 3.1: Ring cleavage / 3.2: Reduction / 4.1: Ring cleavage;
DOI:10.1039/a905440e

Reference yield:

: 108788-48-3
ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

: 247144-50-9
(2S,3R,4R,5S)-1-Benzyl-4-benzyloxy-2-(2-hydroxy-ethyl)-piperidine-3,5-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: TFA; H₂O / 20 °C

2.1: AcOH / methanol / 2 h / -78 °C

2.2: 79 percent / NaCNBH₃; AcOH / methanol / 24 h / 20 °C

3.1: 84 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

With lithium aluminium tetrahydride; water; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; 1.1: Ring cleavage / 2.1: Ring cleavage / 2.2: Reduction / 3.1: Ring cleavage;
DOI:10.1039/a905440e