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

Base Information

Chemical Name:[(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetic acid
CAS No.:741686-22-6
Molecular Formula:C₃₂H₃₇NO₆
Molecular Weight:531.649
Hs Code.:

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

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

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

There total 6 articles about [(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetic acid 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: 97.0%

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

: 741686-22-6
[(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 3h;
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

: 741686-22-6
[(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetic acid

Guidance literature:: Multi-step reaction with 6 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

6.1: 97 percent / LiOH / aq. methanol; tetrahydrofuran / 3 h / 20 °C

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

Reference yield:

: 741686-00-0
ethyl (3R,4S,5R,6R,7R)-3-{allyl[(9H-fluoren-9-yl)methoxycarbonyl]amino}-4,5,6-tris(benzyloxy)-8-[(tert-butyldiphenylsilyl)oxy]-7-hydroxyoctanoate

: 741686-22-6
[(2R,3S,4R,5R,6R)-1-allyl-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)piperidin-2-yl]acetic acid

Guidance literature:: Multi-step reaction with 4 steps

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

2.1: piperidine / dimethylformamide / 0.33 h

2.2: 140 mg / Na₂SO₄; AcOH; NaBH(OAc)3 / 1,2-dichloro-ethane / 6 h

3.1: 73 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

4.1: 97 percent / LiOH / aq. methanol; tetrahydrofuran / 3 h / 20 °C

With piperidine; lithium hydroxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300805