(3R,4R,5R)-5-aminomethyl-3,4-di-O-benzyl-tetrahydrofuran-3-carboxylic acid methyl ester

Base Information

Chemical Name:(3R,4R,5R)-5-aminomethyl-3,4-di-O-benzyl-tetrahydrofuran-3-carboxylic acid methyl ester
CAS No.:1333323-26-4
Molecular Formula:C₂₁H₂₅NO₅
Molecular Weight:371.433
Hs Code.:

Synonyms:(3R,4R,5R)-5-aminomethyl-3,4-di-O-benzyl-tetrahydrofuran-3-carboxylic acid methyl ester

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Chemical Property of (3R,4R,5R)-5-aminomethyl-3,4-di-O-benzyl-tetrahydrofuran-3-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (3R,4R,5R)-5-aminomethyl-3,4-di-O-benzyl-tetrahydrofuran-3-carboxylic acid methyl ester

There total 2 articles about (3R,4R,5R)-5-aminomethyl-3,4-di-O-benzyl-tetrahydrofuran-3-carboxylic acid methyl ester 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: 100.0%

: 1333323-23-1
(3R,4R,5R)-5-azidomethyl-3,4-di-O-benzyltetrahydrofuran-3-carboxylic acid methyl ester

: 1333323-26-4
(3R,4R,5R)-5-aminomethyl-3,4-di-O-benzyl-tetrahydrofuran-3-carboxylic acid methyl ester

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; for 3h;
DOI:10.1007/s00726-011-0849-7

Reference yield:

: 100-39-0
benzyl bromide

: 1333323-26-4
(3R,4R,5R)-5-aminomethyl-3,4-di-O-benzyl-tetrahydrofuran-3-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 0.08 h / Molecular sieve; Inert atmosphere

1.2: 2.5 h / Molecular sieve; Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 3 h

With palladium 10% on activated carbon; hydrogen; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1007/s00726-011-0849-7

Reference yield:

: 1333323-26-4
(3R,4R,5R)-5-aminomethyl-3,4-di-O-benzyl-tetrahydrofuran-3-carboxylic acid methyl ester

: 1333323-29-7
C₄₀H₄₂N₄O₉

Guidance literature:: Multi-step reaction with 2 steps

1.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 19 h / Inert atmosphere

2.1: sodium hydroxide / 1,4-dioxane; water / Inert atmosphere

2.2: Amberlite IR-120 [H⁺] / Inert atmosphere

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In 1,4-dioxane; water; N,N-dimethyl-formamide;
DOI:10.1007/s00726-011-0849-7