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

Base Information

• Chemical Name: D-Proline, 4-hydroxy-5-(hydroxymethyl)-, (4R,5S)- (9CI)
• CAS No.: 159247-18-4
• Molecular Formula: C₆H₁₁NO₄
• Molecular Weight: 161.158
• Mol file: 159247-18-4.mol

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

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

Chemical Property:

• PSA: 0.00000
• LogP: 0.00000

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 152 articles about D-Proline, 4-hydroxy-5-(hydroxymethyl)-, (4R,5S)- (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: 78.0%

(2R,4R,5S)-4-(hydroxy)-5-(hydroxymethyl)-1-N-(p-toluenesulfonyl)pyrrolidine-2-carboxylic acid → (+)-bulgecinine (159247-18-4)

Guidance literature:

With ammonia; sodium; at -70 ℃; for 3h;

DOI:10.1016/j.carres.2020.107931

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