(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-cyclohexylpyrrolidine-2-carboxamide

Base Information

Chemical Name:(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-cyclohexylpyrrolidine-2-carboxamide
CAS No.:1437657-58-3
Molecular Formula:C₃₃H₄₀N₂O₄
Molecular Weight:528.692
Hs Code.:

Synonyms:(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-cyclohexylpyrrolidine-2-carboxamide

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Chemical Property of (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-cyclohexylpyrrolidine-2-carboxamide

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Technology Process of (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-cyclohexylpyrrolidine-2-carboxamide

There total 14 articles about (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-cyclohexylpyrrolidine-2-carboxamide 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: 58.0%

: (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-cyclohexyl-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide

: 1437657-58-3
(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-cyclohexylpyrrolidine-2-carboxamide

Guidance literature:: With water; sodium hydroxide; In methanol; at 20 ℃;
DOI:10.1021/acs.joc.5b00335

Reference yield: 29.0%

: 1437657-25-4
C₃₈H₄₆N₂O₅

: 1437657-58-3
(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-cyclohexylpyrrolidine-2-carboxamide

Guidance literature:: With iodine; In tetrahydrofuran; water; for 0.25h;
DOI:10.1021/ol4012053

Reference yield:

: 100-39-0
benzyl bromide

: 1437657-58-3
(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-cyclohexylpyrrolidine-2-carboxamide

Guidance literature:: Multi-step reaction with 11 steps

1.1: acetyl chloride

1.2: 2 h / 20 °C

2.1: sulfuric acid / acetic acid / 1 h / 100 °C

3.1: sodium tetrahydroborate / ethanol / 5 h / 0 - 20 °C

4.1: triethylamine; dmap / dichloromethane / 144 h

5.1: pyridine / 0 - 4 °C

6.1: sodium azide; 15-crown-5; tetra(n-butyl)ammonium hydrogensulfate / N,N-dimethyl-formamide / 48 h / 100 °C

7.1: toluene-4-sulfonic acid / methanol; chloroform / 6 h

8.1: Dess-Martin periodane / dichloromethane / 0 - 4 °C

9.1: trimethylphosphane / methanol; toluene / 1 h / 0 °C

10.1: methanol / 0 - 4 °C

11.1: iodine / water; tetrahydrofuran / 0.25 h

With pyridine; dmap; sodium tetrahydroborate; sodium azide; 15-crown-5; sulfuric acid; iodine; tetra(n-butyl)ammonium hydrogensulfate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; acetyl chloride; trimethylphosphane; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; acetic acid; N,N-dimethyl-formamide; toluene; 10.1: |Ugi Condensation;
DOI:10.1021/ol4012053