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

Base Information

• Chemical Name: (3R,4R,5R)-5-azidomethyl-3,4-di-O-benzyltetrahydrofuran-3-carboxylic acid methyl ester
• CAS No.: 1333323-23-1
• Molecular Formula: C₂₁H₂₃N₃O₅
• Molecular Weight: 397.431
• Mol file: 1333323-23-1.mol

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

Chemical Property of (3R,4R,5R)-5-azidomethyl-3,4-di-O-benzyltetrahydrofuran-3-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R)-5-azidomethyl-3,4-di-O-benzyltetrahydrofuran-3-carboxylic acid methyl ester

There total 1 articles about (3R,4R,5R)-5-azidomethyl-3,4-di-O-benzyltetrahydrofuran-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: 54.0%

(3R,4R,5R)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylic acid methyl ester + benzyl bromide (100-39-0) → (3R,4R,5R)-5-azidomethyl-3,4-di-O-benzyltetrahydrofuran-3-carboxylic acid methyl ester (1333323-23-1) + (3R,4R,5R)-5-azidomethyl-3,4-di-O-benzyl-tetrahydrofuran-3-carboxylic acid benzyl ester (1333323-24-2)

Guidance literature:

(3R,4R,5R)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylic acid methyl ester; benzyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; for 0.0833333h; Molecular sieve; Inert atmosphere;

With sodium hydride; In N,N-dimethyl-formamide; for 2.5h; Molecular sieve; Inert atmosphere;

DOI:10.1007/s00726-011-0849-7

Reference yield: 100.0%

(3R,4R,5R)-5-azidomethyl-3,4-di-O-benzyltetrahydrofuran-3-carboxylic acid methyl ester (1333323-23-1) → (3R,4R,5R)-5-aminomethyl-3,4-di-O-benzyl-tetrahydrofuran-3-carboxylic acid methyl ester (1333323-26-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; for 3h;

DOI:10.1007/s00726-011-0849-7

Reference yield:

(3R,4R,5R)-5-azidomethyl-3,4-di-O-benzyltetrahydrofuran-3-carboxylic acid methyl ester (1333323-23-1) → C41H46N2O9 (1333323-31-1)

Guidance literature:

Multi-step reaction with 3 steps

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

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

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

With palladium 10% on activated carbon; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1007/s00726-011-0849-7

upstream raw materials:

benzyl bromide

Downstream raw materials:

C₄₀H₄₂N₄O₉

C₄₁H₄₆N₂O₉

(3R,4R,5R)-5-azidomethyl-3,4-di-O-benzyl-tetrahydrofuran-3-carboxylic acid

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