L-Proline, 4-hydroxy-5-(hydroxymethyl)-, (4S,5R)- (9CI)

Base Information

• Chemical Name: L-Proline, 4-hydroxy-5-(hydroxymethyl)-, (4S,5R)- (9CI)
• CAS No.: 95863-87-9
• Molecular Formula: C₆H₁₁NO₄
• Molecular Weight: 161.158
• Mol file: 95863-87-9.mol

Synonyms:L-Proline,4-hydroxy-5-(hydroxymethyl)-, (2a,4a,5b)-; (-)-Bulgecinine; Bulgecinine

Chemical Property of L-Proline, 4-hydroxy-5-(hydroxymethyl)-, (4S,5R)- (9CI)

Chemical Property:

• PSA: 89.79000
• LogP: -1.51650

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Proline, 4-hydroxy-5-(hydroxymethyl)-, (4S,5R)- (9CI)

There total 105 articles about L-Proline, 4-hydroxy-5-(hydroxymethyl)-, (4S,5R)- (9CI) 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: 90.0%

(2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (95863-88-0) → (2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid (95863-87-9,159247-18-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃;

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

Reference yield: 82.0%

Methanesulfonic acid (S)-2-((2S,4S)-4-amino-5-oxo-tetrahydro-furan-2-yl)-2-hydroxy-ethyl ester (108428-47-3) → (2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid (95863-87-9,159247-18-4) + 2,4-cis-4,5-trans-4,5-dihydroxypipecolic acid (38146-56-4)

Guidance literature:

With potassium hydroxide; In ethanol; at 20 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(00)84755-3

Reference yield: 70.0%

(2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-(2-trimethylsilanyl-ethyl) ester (132592-40-6) → (2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid (95863-87-9,159247-18-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; a) 24h, c) 2h, 50-60 deg C;

DOI:10.1021/jo00008a040

upstream raw materials:

(5R,4S,2S)-4-acetoxy-5-hydroxymethyl-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) diester

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

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

(2S,4S,5S)-5-bromo-2-<<(tert-butyl)oxycarbonyl>amino>-6-hydroxyhexano-4-lactone

Downstream raw materials:

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

(1S,4S,6R)-6-Hydroxymethyl-3-oxo-2-oxa-5-aza-bicyclo[2.2.1]heptane-5-carboxylic acid benzyl ester

(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-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester; compound with dicyclohexyl-amine

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