(2S,3S,4S,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid benzylamide

Base Information

• Chemical Name: (2S,3S,4S,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid benzylamide
• CAS No.: 258501-85-8
• Molecular Formula: C₂₃H₃₈N₂O₅Si
• Molecular Weight: 450.651
• Mol file: 258501-85-8.mol

Synonyms:(2S,3S,4S,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid benzylamide

Chemical Property of (2S,3S,4S,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid benzylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid benzylamide

There total 1 articles about (2S,3S,4S,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid benzylamide 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: 91.0%

benzylamine (100-46-9) + Trifluoro-methanesulfonic acid (R)-((2R,3S,4S)-4-amino-5-oxo-3-triethylsilanyloxy-tetrahydro-furan-2-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester (196494-69-6) → (2S,3S,4S,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid benzylamide (258501-85-8)

Guidance literature:

In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(99)01844-4

Reference yield: 60.0%

(2S,3S,4S,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid benzylamide (258501-85-8) → (2S,3S,4S,5S)-5-((S)-1,2-Dihydroxy-ethyl)-3,4-dihydroxy-pyrrolidine-2-carboxylic acid benzylamide (258502-00-0)

Guidance literature:

In water; trifluoroacetic acid;

DOI:10.1016/S0040-4039(99)01844-4

Reference yield:

(2S,3S,4S,5R)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-3-triethylsilanyloxy-pyrrolidine-2-carboxylic acid benzylamide (258501-85-8) → (2R,3S,4S,5S)-2-(Benzylamino-methyl)-5-((S)-1,2-dihydroxy-ethyl)-pyrrolidine-3,4-diol

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / H₂O; trifluoroacetic acid

2: 74 percent / imidazole / dimethylformamide / 80 °C

3: BH₃*SMe₂ / tetrahydrofuran / Heating

4: 90 percent / H₂O; trifluoroacetic acid

With 1H-imidazole; dimethylsulfide borane complex; In tetrahydrofuran; water; N,N-dimethyl-formamide; trifluoroacetic acid; 1: Hydrolysis / 2: silylation / 3: Reduction / 4: Hydrolysis;

DOI:10.1016/S0040-4039(99)01844-4

upstream raw materials:

benzylamine

Trifluoro-methanesulfonic acid (R)-((2R,3S,4S)-4-amino-5-oxo-3-triethylsilanyloxy-tetrahydro-furan-2-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester

Downstream raw materials:

(2S,3S,4S,5S)-5-((S)-1,2-Dihydroxy-ethyl)-3,4-dihydroxy-pyrrolidine-2-carboxylic acid benzylamide

(2S,3S,4S,5S)-5-((S)-1,2-Bis-triethylsilanyloxy-ethyl)-3,4-bis-triethylsilanyloxy-pyrrolidine-2-carboxylic acid benzylamide