cis-4-Hydroxy-D-proline Chemical Properties

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. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Water (Slightly)

form 

Powder

pka

2.14±0.40(Predicted)

color 

White

optical activity

56.1°(C=0.93 g/100ml H2O)

Water Solubility 

5 g/100 mL

BRN 

81439

InChIKey

PMMYEEVYMWASQN-QWWZWVQMSA-N

LogP

-1.840 (est)

CAS DataBase Reference

2584-71-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-22-36/37/39-27-26

WGK Germany 

3

F 

10

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

cis-4-Hydroxy-D-proline Usage And Synthesis

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

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

cis-4-Hydroxy-D-proline(2584-71-6)Related Product Information

• D-Proline
• CHLOROPHOSPHONAZO III
• L-PROLINE-(4-3H(N))
• cis-Octahydro-isoindole
• alpha-Cypermethrin
• L-Proline
• L-Hydroxyproline
• trans-4-Hydroxy-D-proline
• CIS-4-HYDROXY-L-PROLINE,CIS-4-HYDROXY-L-PROLINE NATURAL ISOMER
• CIS-4-HYDROXY-D-PROLINE HCL ,cis-4-Hydroxy-D-proline hydrochloride
• CIS-4-HYDROXY-L-PROLINE METHYL ESTER HCL,CIS-4-HYDROXY-L-PROLINE METHYL ESTER HYDROCHLORIDE
• cis-4-Hydroxycyclohexanecarboxylic acid
• Cyclohexanecarboxylic acid, 4-hydroxy-, Methyl ester, cis-
• (4S)-4-hydroxy-L-proline hydrochloride
• cis-2,6-Dimethylpiperidine
• cis-2,6-Dimethylmorpholine
• cis-2,6-Dimethylpiperazine
• CIS-1,2,3,6-TETRAHYDROPHTHALIMIDE