Lot numbers can be found on the outside label of a product:
N-Boc-cis-4-Hydroxy-D-proline
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CAS No. 135042-12-5
- Cat. No. CS-W002887
- Purity≥97%
- MDL No.MFCD02094407
*For research and further manufacturing use only, not for direct human use.
Structure of 135042-12-5
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General Information
- CAS No. 135042-12-5
- Cat. No. CS-W002887
- Purity ≥97%
- MDL No. MFCD02094407
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₀H₁₇NO₅
- Molecular Weight None
- Synonym(s) None
- SMILES CC(C)(C)OC(N1[C@H](C[C@H](C1)O)C(O)=O)=O
Description
N-Boc-cis-4-Hydroxy-D-proline is a stereochemically defined proline derivative featuring a cis-configured hydroxyl group at the C4 position and a robust Boc protecting group. This configuration enhances its utility in peptide synthesis, particularly for incorporating constrained D-hydroxyproline motifs into bioactive sequences. The molecule exhibits excellent stability under standard bench conditions and facilitates efficient incorporation into cyclic or linear peptides without racemization.
Application
N-Boc-cis-4-Hydroxy-D-proline serves as a key chiral building block for the synthesis of peptidomimetics and bioactive heterocycles. Its cis-configured pyrrolidine ring and protected amine enable efficient incorporation into peptide backbones, while the 4-hydroxyl group facilitates downstream functionalization via oxidation or glycosylation. The Boc group ensures stability during storage and compatibility with standard coupling protocols, offering predictable reactivity in solid-phase and solution-phase synthesis.
Synthesis
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References
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WARNER-LAMBERT COMPANY LLC Patent: WO2006/38119 A1, 2006 ; Location in patent: Page/Page column 19 ;
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Route2
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1070-19-5 -
In-stock
2584-71-6 - ~85%
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In-stock
135042-12-5
References
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Nakamura, Takako; Matsuyama, Haruo; Kamigata, Nobumasa; Iyoda, Masahiko Journal of Organic Chemistry, 1992 , vol. 57, # 14 p. 3783 - 3789
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References
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Pandey, Anil K.; Naduthambi, Devan; Thomas, Krista M.; Zondlo, Neal J. Journal of the American Chemical Society, 2013 , vol. 135, # 11 p. 4333 - 4363
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 87.07
- LogP 0.4413
- H_Acceptors 4
- H_Donors 2
- Rotatable_Bonds 1
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Other Classifications
- Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives
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- Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Antibody-Drug Conjugates (ADC) Preparation Research Reagents Cross-Linkers
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Key Words
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