(3S,4S,5R)-1-benzyl-5-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3,4-dihydroxypiperidine

Base Information

Chemical Name:(3S,4S,5R)-1-benzyl-5-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3,4-dihydroxypiperidine
CAS No.:849402-63-7
Molecular Formula:C₂₅H₃₄N₂O₄
Molecular Weight:426.556
Hs Code.:

Synonyms:(3S,4S,5R)-1-benzyl-5-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3,4-dihydroxypiperidine

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Chemical Property of (3S,4S,5R)-1-benzyl-5-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3,4-dihydroxypiperidine

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Technology Process of (3S,4S,5R)-1-benzyl-5-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3,4-dihydroxypiperidine

There total 4 articles about (3S,4S,5R)-1-benzyl-5-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3,4-dihydroxypiperidine 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: 42.0%

: 849402-62-6
(2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine

: 849402-63-7
(3S,4S,5R)-1-benzyl-5-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3,4-dihydroxypiperidine

Guidance literature:: (2R,3S,4R)-1-benzyl-4-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3-hydroxy-2-hydroxymethylpyrrolidine; With trifluoroacetic anhydride; In tetrahydrofuran; at -78 ℃; for 3h;

With triethylamine; for 17h; Heating;

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 2h;
DOI:10.3987/COM-04-S(P)13

Reference yield:

: 849402-57-9
(2R,3S,4S)-1-benzyl-4-benzylaminomethyl-3-hydroxy-2-hydroxymethylpyrrolidine

: 849402-63-7
(3S,4S,5R)-1-benzyl-5-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3,4-dihydroxypiperidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 69 percent / triethylamine / CH₂Cl₂ / 4 h / 0 °C

2.1: trifluoroacetic anhydride / tetrahydrofuran / 3 h / -78 °C

2.2: triethylamine / 17 h / Heating

2.3: 42 percent / NaOH / tetrahydrofuran; H₂O / 2 h / 20 °C

With triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane;
DOI:10.3987/COM-04-S(P)13

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 849402-63-7
(3S,4S,5R)-1-benzyl-5-(N-benzyl-N-tert-butyloxycarbonylamino)methyl-3,4-dihydroxypiperidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 69 percent / triethylamine / CH₂Cl₂ / 4 h / 0 °C

2.1: trifluoroacetic anhydride / tetrahydrofuran / 3 h / -78 °C

2.2: triethylamine / 17 h / Heating

2.3: 42 percent / NaOH / tetrahydrofuran; H₂O / 2 h / 20 °C

With triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane;
DOI:10.3987/COM-04-S(P)13