D-Proline, 3,4-dihydroxy-, (3R,4R)- (9CI)

Base Information

• Chemical Name: D-Proline, 3,4-dihydroxy-, (3R,4R)- (9CI)
• CAS No.: 302593-22-2
• Molecular Formula: C₅H₉NO₄
• Molecular Weight: 147.131
• Mol file: 302593-22-2.mol

Synonyms:D-Proline, 3,4-dihydroxy-, (3R,4R)- (9CI)

Chemical Property of D-Proline, 3,4-dihydroxy-, (3R,4R)- (9CI)

Chemical Property:

• Boiling Point: 411.5±45.0 °C(Predicted)
• PKA: 1.82±0.60(Predicted)
• PSA: 89.79000
• Density: 1.617±0.06 g/cm3(Predicted)
• LogP: -1.90660

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-Proline, 3,4-dihydroxy-, (3R,4R)- (9CI)

There total 10 articles about D-Proline, 3,4-dihydroxy-, (3R,4R)- (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:

(2S,3R,4R)-4-Azido-3-hydroxy-5-oxo-tetrahydro-furan-2-carbaldehyde (111651-95-7) → 2R,3R,4R-dihydroxyproline (302593-22-2,654083-19-9)

Guidance literature:

With hydrogen; palladium; In water; for 96h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(01)89972-5

Reference yield:

Methyl 2-azido-2-deoxy-3,4:5,6-O-diisopropylidene-L-idonate → 2R,3R,4R-dihydroxyproline (302593-22-2,654083-19-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: H₂ / 10 percent Pd/C / ethyl acetate / 5 h / 20 °C

2.1: 6.14 g / Pb(NO₃)2; Et₃N / CH₂Cl₂ / 48 h / 20 °C

3.1: 95 percent / Dowex 50W-X₈ / methanol / 20 h / 20 °C

4.1: aq. NaIO₄ / ethanol / 1 h / 20 °C

5.1: 0.80 g / NaBH₄ / aq. ethanol / 0.5 h / 0 °C

6.1: 96 percent / Et₃N / tetrahydrofuran / 0.25 h / 0 °C

7.1: I₂ / methanol / 8 h / Heating

7.2: Dowx 50W-X₈ / methanol / 2 h / Heating

With sodium tetrahydroborate; sodium periodate; lead(II) nitrate; Dowex 50W-X₈; hydrogen; iodine; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; 1.1: Reduction / 2.1: Substitution / 3.1: Ring cleavage / 4.1: Oxidation / 5.1: Reduction / 6.1: Substitution / 7.1: Cyclization / 7.2: Substitution;

DOI:10.1055/s-2000-6408

Reference yield:

α-D-glucurono-γ-lactone (14362-29-9) → 2R,3R,4R-dihydroxyproline (302593-22-2,654083-19-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / sulphuric acid conc. / 4 h / Ambient temperature

2: 99 percent / CH₂Cl₂ / 1.5 h / -40 °C

3: 83 percent / sodium azide / dimethylformamide / 2.5 h / -20 °C

4: 82 percent / trifluoroacetic acid-water (3:1) / 3.5 h / Ambient temperature

5: sodium periodate / aq. ethanol / 0.42 h / Ambient temperature

6: H₂ / Pd / H₂O / 96 h / Ambient temperature

With sodium periodate; sodium azide; sulfuric acid; hydrogen; trifluoroacetic acid; palladium; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)89972-5

upstream raw materials:

(2S,3R,4R)-4-Azido-3-hydroxy-5-oxo-tetrahydro-furan-2-carbaldehyde

N-Tosyl-2,3-trans-3,4-trans-3,4-dihydroxy-L-prolin

methyl 2-deoxy-3,4-O-isopropylidene-5-O-methanesulfonyl-2-[(9-phenyl-9-fluorenyl)-amino]-D-arabinonate

α-D-glucurono-γ-lactone

Refernces

• 1、 Bashyal, Bharat P.,Chow, Hak-Fun,Fellows, Linda E.,Fleet, George W. J.. "THE SYNTHESIS OF POLYHYDROXYLATED AMINO ACIDS FROM GLUCURONOLACTONE: ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE". . p. 415 - 422. Retrieved 2007/10/02.