ethyl [(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetate

Base Information

Chemical Name:ethyl [(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetate
CAS No.:741686-18-0
Molecular Formula:C₃₄H₄₁NO₆
Molecular Weight:559.703
Hs Code.:

Synonyms:ethyl [(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetate

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Chemical Property of ethyl [(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetate

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Technology Process of ethyl [(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetate

There total 5 articles about ethyl [(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetate 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: 73.0%

: 741686-07-7
ethyl [(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}piperidin-2-yl]acetate

: 741686-18-0
ethyl [(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1002/ejoc.200300805

Reference yield:

: 741685-83-6
ethyl (3R,4S,5R,6R,7R)-3-(allylamino)-4,5,6-tris(benzyloxy)-7,8-dihydroxyoctanoate

: 741686-18-0
ethyl [(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

2.1: 96 percent / aq. Na₂CO₃ / dioxane / 2 h

3.1: PCC; molecular sieves (4 Angstroem) / CH₂Cl₂ / 12 h

4.1: piperidine / dimethylformamide / 0.33 h

4.2: 140 mg / Na₂SO₄; AcOH; NaBH(OAc)3 / 1,2-dichloro-ethane / 6 h

5.1: 73 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

With piperidine; 1H-imidazole; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium carbonate; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300805

Reference yield:

: 741685-92-7
ethyl (3R,4S,5R,6R,7R)-3-(allylamino)-4,5,6-tris(benzyloxy)-8-[(tert-butyldiphenylsilyl)oxy]-7-hydroxyoctanoate

: 741686-18-0
ethyl [(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / aq. Na₂CO₃ / dioxane / 2 h

2.1: PCC; molecular sieves (4 Angstroem) / CH₂Cl₂ / 12 h

3.1: piperidine / dimethylformamide / 0.33 h

3.2: 140 mg / Na₂SO₄; AcOH; NaBH(OAc)3 / 1,2-dichloro-ethane / 6 h

4.1: 73 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

With piperidine; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium carbonate; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300805