(2R,3R,4R,5S,6S)-4-Benzyloxy-2-benzyloxymethyl-6-vinyl-piperidine-3,5-diol

Base Information

Chemical Name:(2R,3R,4R,5S,6S)-4-Benzyloxy-2-benzyloxymethyl-6-vinyl-piperidine-3,5-diol
CAS No.:606970-48-3
Molecular Formula:C₂₂H₂₇NO₄
Molecular Weight:369.461
Hs Code.:

Synonyms:(2R,3R,4R,5S,6S)-4-Benzyloxy-2-benzyloxymethyl-6-vinyl-piperidine-3,5-diol

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Chemical Property of (2R,3R,4R,5S,6S)-4-Benzyloxy-2-benzyloxymethyl-6-vinyl-piperidine-3,5-diol

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Technology Process of (2R,3R,4R,5S,6S)-4-Benzyloxy-2-benzyloxymethyl-6-vinyl-piperidine-3,5-diol

There total 4 articles about (2R,3R,4R,5S,6S)-4-Benzyloxy-2-benzyloxymethyl-6-vinyl-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: 66.0%

: 606970-47-2
(S)-1-((3aS,5S,6R,6aS)-6-Benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-allylamine

: 606970-48-3
(2R,3R,4R,5S,6S)-4-Benzyloxy-2-benzyloxymethyl-6-vinyl-piperidine-3,5-diol

Guidance literature:: (S)-1-((3aS,5S,6R,6aS)-6-Benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-allylamine; With trifluoroacetic acid; In water; for 36h;

With sodium cyanoborohydride; acetic acid; In methanol; for 24h;
DOI:10.1021/ol035117h

Reference yield:

: 302788-33-6
3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydo-hexos-5-ulo-2,5-furanose

: 606970-48-3
(2R,3R,4R,5S,6S)-4-Benzyloxy-2-benzyloxymethyl-6-vinyl-piperidine-3,5-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / CH₂Cl₂ / 2 h / 4 °C

2.1: 76 percent / diethyl ether / 24 h / 0 - 20 °C

3.1: 80 percent / Ndimethylbarbituric acid / Pd(PPh₃)4 / CH₂Cl₂ / 3 h / 35 °C

4.1: TFA / H₂O / 36 h

4.2: 66 percent / NaBH₃CN; AcOH / methanol / 24 h

With 1,3-dimethylbarbituric acid; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In diethyl ether; dichloromethane; water;
DOI:10.1021/ol035117h

Reference yield:

: Allyl-[1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-meth-(E)-ylidene]-amine

: 606970-48-3
(2R,3R,4R,5S,6S)-4-Benzyloxy-2-benzyloxymethyl-6-vinyl-piperidine-3,5-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 76 percent / diethyl ether / 24 h / 0 - 20 °C

2.1: 80 percent / Ndimethylbarbituric acid / Pd(PPh₃)4 / CH₂Cl₂ / 3 h / 35 °C

3.1: TFA / H₂O / 36 h

3.2: 66 percent / NaBH₃CN; AcOH / methanol / 24 h

With 1,3-dimethylbarbituric acid; trifluoroacetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In diethyl ether; dichloromethane; water;
DOI:10.1021/ol035117h