Name | N-t-BOC-cis-4-hydroxy-L-proline |
Synonyms | cis-boc-Hyp-OH CIS-BOC-L-HYP-OH BOC-cis-4-hydroxy-L-proline N-Boc-cis-4-hydroxy-L-proine N-Boc-Cis-4-Hydroxy-L-Proline cis-N-Boc-4-hydroxy-L-proline N-t-BOC-cis-4-hydroxy-L-proline N-(tert-butoxycarbonyl)-cis-4-hydroxy-L-proline (4S)-1-(tert-butoxycarbonyl)-4-hydroxy-L-proline N-Boc-cis-4-hydroxypyrrolidine-2-carboxylic acid cis-1-(tert-Butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (2S,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (2S,4S)-cis-1-N-Boc-4-hydroxy-proline, N- Boc-cis-4-hydroxypyrrolidine-2-carboxylic acid |
CAS | 87691-27-8 |
EINECS | 627-315-1 |
InChI | InChI=1/C10H17NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h6-7,12H,4-5H2,1-3H3,(H,13,14)/t6-,7-/m0/s1 |
InChIKey | BENKAPCDIOILGV-BQBZGAKWSA-N |
Molecular Formula | C10H17NO5 |
Molar Mass | 231.25 |
Density | 1.312±0.06 g/cm3(Predicted) |
Melting Point | 146 °C (D) (lit.) |
Boling Point | 390.9±42.0 °C(Predicted) |
Specific Rotation(α) | -50 º (c=0.67, MeOH) |
Flash Point | 190.2°C |
Vapor Presure | 9.99E-08mmHg at 25°C |
Appearance | Powder or Crystalline Powder |
Color | White to off-white |
pKa | 3.80±0.40(Predicted) |
Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
Refractive Index | 1.531 |
MDL | MFCD02094406 |
Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R50 - Very Toxic to aquatic organisms |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
UN IDs | UN 3077 9 / PGIII |
WGK Germany | 3 |
HS Code | 29339900 |
Hazard Class | IRRITANT |
Introduction | the melting point of N-Boc-cis-4-hydroxy-l-proline is 146°C(D). (lit.), the specific optical rotation is -50 °(c = 0.67,MeOH), the boiling point is 390.9±42.0 ° c (Predicted), the density is 1.312±0.06g/cm3(Predicted), and the acidity coefficient (pKa). Is 3.80±0.40(Predicted). Proline derivative N-Boc-cis-4-hydroxy-l-proline is a kind of important organic functional compounds which can be used in medicine, agriculture, chemistry and other fields. |
uses | the unnatural amino acid N-Boc-cis-4-hydroxyproline is a very important class of small organic molecules, it is often used to modify the synthesis of peptides, improve the resistance to proteolytic enzyme degradation, and regulate the physical and biochemical properties of bioactive peptides and asymmetric chiral inducers. |
synthetic method | commercially available (Aldrich) compound 6(525mg,4mmol) was dissolved in water (10ml) and THF(5L). NaOH (aqueous solution) was added to bring the pH to 9-10. Boc anhydride (959mg,4.4mmol) was dissolved in THF(2ml) and added dropwise to the reaction. The reaction was maintained at pH 9-10 with NaOH (aqueous). After completion, the reaction was acidified to pH 3 with dilute HCl (AQ) and extracted with EtOAc(2x). The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain Boc-protected proline (compound 6a). The solid was washed with hexane (3x) and dried under high vacuum to give an intermediate. Solid 1, 5-cis-4-hydroxy-l-proline, yield (N-Boc mg,95%). |