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trans-4-Hydroxy-D-proline

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Name

trans-4-Hydroxy-D-proline

EINECS 219-963-5
CAS No. 3398-22-9 Density 1.395 g/cm3
PSA 69.56000 LogP -0.87740
Solubility N/A Melting Point 260°C
Formula C5H9NO3 Boiling Point 355.2 °C at 760 mmHg
Molecular Weight 131.131 Flash Point 168.6 °C
Transport Information N/A Appearance White crystal or crystalline powder
Safety 24/25-36/37-26 Risk Codes 22-36/37/38-43
Molecular Structure Molecular Structure of 3398-22-9 (trans-4-Hydroxy-D-proline) Hazard Symbols HarmfulXn
Synonyms

D-Proline,4-hydroxy-, trans-;(2R,4S)-(+)-4-Hydroxy-D-proline;4-(S)-Hydroxypyrrolidine-2-(R)-carboxylic acid;D-Hydroxyproline;D-trans-4-Hydroxyproline;NSC 206273;trans-4-Hydroxy-D-proline;

Article Data 9

trans-4-Hydroxy-D-proline Synthetic route

(2R,4S)-4-(benzyloxy)-1-N-tosylpyrrolidine-2-carboxylic acid

3398-22-9

trans-4-hydroxyproline

Conditions
ConditionsYield
With ammonia; sodium at -70℃; for 3.5h; Inert atmosphere;79%
77449-96-8

N-Acetyl-allo-4-(p-toluenesulfonyloxy)-D-proline

3398-22-9

trans-4-hydroxyproline

Conditions
ConditionsYield
With sodium hydroxide Erhitzen des Reaktionsprodukts mit wss. HCl;
114673-33-5

trans-1-(3,5-dinitro-benzoyl)-4-hydroxy-D-proline

3398-22-9

trans-4-hydroxyproline

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride
1-anilinoformyl-d-a-<4-oxy-proline >

1-anilinoformyl-d-a-<4-oxy-proline >

3398-22-9

trans-4-hydroxyproline

Conditions
ConditionsYield
With ammonia at 95 - 100℃;
77449-96-8

N-Acetyl-allo-4-(p-toluenesulfonyloxy)-D-proline

aqueous NaOH

aqueous NaOH

3398-22-9

trans-4-hydroxyproline

Conditions
ConditionsYield
anschliessend Erhitzen mit wss. HCl;
618-28-0

trans-4-hydroxy-D,L-proline

3398-22-9

trans-4-hydroxyproline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous NaOH
2: (1S,2S)-2-amino-1-<4-nitro-phenyl>-propane-1,3-diol
3: aqueous HCl
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide
2: (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol
3: hydrogenchloride
View Scheme
77449-95-7

N-Acetyl-allo-4-(p-toluenesulfonyloxy)-D-proline Methyl Ester

3398-22-9

trans-4-hydroxyproline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous methanol. NaOH
2: aqueous NaOH / Erhitzen des Reaktionsprodukts mit wss. HCl
View Scheme
103078-90-6, 114673-32-4, 114673-33-5

trans-1-(3,5-dinitro-benzoyl)-4-hydroxy-DL-proline

3398-22-9

trans-4-hydroxyproline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: brucine
2: aqueous HCl
View Scheme
Multi-step reaction with 2 steps
1: (1S,2S)-2-amino-1-<4-nitro-phenyl>-propane-1,3-diol
2: aqueous HCl
View Scheme
Multi-step reaction with 2 steps
1: (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol
2: hydrogenchloride
View Scheme
618-28-0

trans-4-hydroxy-D,L-proline

A

3398-22-9

trans-4-hydroxyproline

B

51-35-4

4R-4-hydroxyproline

Conditions
ConditionsYield
With shaking calcined L-Pro chiral ordered mesoporous silica Resolution of racemate;

(3S,5R)-3-(benzyloxy)-2-hydroxy-5-(hydroxymethyl)-1-N-tosylpyrrolidine

3398-22-9

trans-4-hydroxyproline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 30 °C / Inert atmosphere
2: Jones reagent / acetone / 4 h / 0 °C / Inert atmosphere
3: ammonia; sodium / 3.5 h / -70 °C / Inert atmosphere
View Scheme

trans-4-Hydroxy-D-proline Chemical Properties

Molecular Formula:C5H9NO3
Molar mass:131.12986g/mol
Structure of trans-4-Hydroxy-D-proline(3398-22-9):
                         
Synonyms of trans-4-Hydroxy-D-proline(3398-22-9):L-Hydroxyproline;H-D-PRO(4-HYDROXY)-OH;H-D-PRO(TRANS-4-HYDROXY)-OH;H-D-HYP-OH;Proline, 4-hydroxy-;TRANS-D-HYDROXYPROLINE;4-Hydroxiproline(2R,4S)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;
Density:1.395 g/cm3                              
Flash Point:168.6 °C                 
Boiling Point:355.2 °C at 760 mmHg       
Index of Refraction:1.54            
Vapour Pressure:1.8E-06 mmHg at 25°C  
Melting point:260°C

trans-4-Hydroxy-D-proline Safety Profile

Hazard Codes:Xn
Risk Statements:
22:  Harmful if swallowed 
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin
43:  May cause sensitization by skin contact 
Safety Statements:
24:  Avoid contact with skin
25:  Avoid contact with eyes
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice36:  Wear suitable protective clothing 
37:  Wear suitable gloves

trans-4-Hydroxy-D-proline Specification

Product Categories of trans-4-Hydroxy-D-proline(3398-22-9):Pyrrolidines;Carboxylic Acids;Carboxylic Acids;Chiral Compound

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