ChemicalBook CAS DataBase List 2584-71-6

2584-71-6

Name	cis-4-Hydroxy-D-proline
CAS	2584-71-6
EINECS(EC#)	219-963-5
Molecular Formula	C5H9NO3
MDL Number	MFCD00005252
Molecular Weight	131.13
MOL File	2584-71-6.mol

Synonyms

(2R,4R)-(-)-4-HYDROXY-2-PYRROLINECARBOXYLIC ACID (2R,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID (4R,2R)-4-HYDROXY-PYRROLIDINE-2-CARBOXYLIC ACID CIS-4-HYDROXY-D-PROLINE CIS-D-4-HYDROXYPROLINE CIS-D-HYDROXYPROLINE D-ALLO-4-HYDROXY-2-PYRROLIDINE-CARBOXYLIC ACID D-ALLO-HYDROXYPROLINE D-CIS-4-HYDROXYPROLINE D-CIS-HYDROXYPROLINE H-D-CIS-HYP-OH HYDROXY-D-PROLINE [ALLO] D-trans-Hydroxyproline cis-4-D-Hydroxyproline (2R,4R)-(+)-4-Hydroxy-2-pyrrolidinecarboxylic acid D-ALLO-4-HYDROXYPROLINE D-Proline, 4-hydroxy-, (4R)- (2R,4R)-(-)-4-Hydroxypyrrolidin-2-ylcarboxylic acid D-CIS-HYDROXYPROLINE, (2R,4R)-(-)-4-HYDROXY-2-PYRROLINECARBOXYLIC ACID (2R,4R)-4-HYDROXY-D-PROLINE

Chemical Properties

Appearance	white powder
Melting point	243 °C (dec.)(lit.)
alpha	58 º (c=2, water 24 ºC)
Boiling point	242.42°C (rough estimate)
density	1.3121 (rough estimate)
refractive index	1.4300 (estimate)
storage temp.	Store at RT.
solubility	Water (Slightly)
form	Powder
pka	2.14±0.40(Predicted)
color	White
Optical Rotation	56.1°(C=0.93 g/100ml H2O)
Water Solubility	5 g/100 mL
BRN	81439
InChI	1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m1/s1
InChIKey	PMMYEEVYMWASQN-QWWZWVQMSA-N
SMILES	O[C@H]1CN[C@H](C1)C(O)=O
LogP	-1.840 (est)
CAS DataBase Reference	2584-71-6(CAS DataBase Reference)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H315-H319-H335
Precautionary statements	P261-P271-P280
Hazard Codes	Xi
Risk Statements	R36/37/38:Irritating to eyes, respiratory system and skin . less more
Safety Statements	S24/25:Avoid contact with skin and eyes . S22:Do not breathe dust . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S27:Take off immediately all contaminated clothing . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . less more
WGK Germany	3
F	10
HS Code	29339900
Storage Class	13 - Non Combustible Solids

Hazard Information

Chemical Properties

white powder

Uses

cis-4-Hydroxy-D-proline (cas# 2584-71-6) is a compound useful in organic synthesis.

Definition

ChEBI: D-proline in which a hydrogen at the 4-position of the pyrrolidine ring is substituted by a hydroxy group (R-configuration).

Biochem/physiol Actions

Cis-4-Hydroxy-D-proline may be used as a starting material for the 13-step synthesis of new conformationally restricted PNA adenine monomer and the synthesis of N-Benzyl pyrrolidinyl sordaricin derivatives. Cis-4-Hydroxy-D-proline is a substrate that may be used to study the specificity and kinetics of D-alanine dehydrogenase. Cis-4-Hydroxy-D-proline may be used to analyze the substrate specificity of amino acid transporter PAT1.

Synthesis

51-35-4

2584-71-6

General procedure for the synthesis of cis-4-hydroxy-D-proline using L-hydroxyproline as starting material: a synthetic route has been successfully developed for the other two stereoisomers in the pro4 monomer class. A controlled differential isomerization strategy [34] was employed to convert 30 g of trans-4-hydroxy-(L)-proline 5 into its diastereoisomer cis-4-hydroxy-(D)-proline 14 in 57% isolated yield. Further processing of the intermediate by the synthetic method described in Scheme 1 allowed the synthesis of two additional enantiomers of the pro4 structural unit class 3, pro4(2R,4R) and pro4(2R,4S) (see Scheme 3 for details).

References

[1] Tetrahedron Asymmetry, 2003, vol. 14, # 20, p. 3141 - 3152
[2] Tetrahedron Asymmetry, 2002, vol. 13, # 2, p. 197 - 201
[3] Tetrahedron, 2009, vol. 65, # 4, p. 862 - 876
[4] Patent: US2004/77879, 2004, A1. Location in patent: Page 13
[5] Patent: WO2018/13867, 2018, A1. Location in patent: Paragraph 339

Spectrum Detail

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