(2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Base Information

• Chemical Name: (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester
• CAS No.: 95863-88-0
• Molecular Formula: C₁₄H₁₇NO₆
• Molecular Weight: 295.292
• Mol file: 95863-88-0.mol

Synonyms:(2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Chemical Property of (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

There total 27 articles about (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl 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: 88.0%

benzyl (2S,4S,5R)-4-acetoxy-2-carboxy-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1-carboxylate (337975-48-1) → (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (95863-88-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; Heating;

DOI:10.1016/S0040-4039(01)00071-5

Reference yield:

benzyl (2R,3S,5S)-3-acetoxy-2-((tert-butyldimethylsilyloxy)methyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate (337975-50-5) → (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (95863-88-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / NaIO₄ / RuCl₃ / acetonitrile; CCl₄; H₂O / 0 °C

2: 88 percent / aq. HCl / tetrahydrofuran / Heating

With hydrogenchloride; sodium periodate; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(01)00071-5

Reference yield:

Acetic acid (2R,3S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-pyrrolidin-3-yl ester → (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (95863-88-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / aq. NaHCO₃ / CH₂Cl₂ / 20 °C

2: 80 percent / NaIO₄ / RuCl₃ / acetonitrile; CCl₄; H₂O / 0 °C

3: 88 percent / aq. HCl / tetrahydrofuran / Heating

With hydrogenchloride; sodium periodate; sodium hydrogencarbonate; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(01)00071-5

upstream raw materials:

(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid

benzyl chloroformate

benzyl (2S,4S,5R)-4-acetoxy-2-carboxy-5-[(tert-butyldimethylsilyloxy)methyl]pyrrolidine-1-carboxylate

benzyl (2R,3S,5S)-3-acetoxy-2-((tert-butyldimethylsilyloxy)methyl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate

Downstream raw materials:

(2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester

(2S,4S,5R)-4-Acetoxy-5-acetoxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

(2R,4S,5S)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-2-carboxylic acid

(2S,4S,5S)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-2-carboxylic acid