Cas no 88971-40-8 (L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-)

L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-, is a protected derivative of L-alanine featuring two tert-butoxycarbonyl (Boc) groups. This compound is primarily used in peptide synthesis, where the Boc groups serve as protective moieties for the amino and carboxyl functionalities, ensuring selective reactivity during coupling reactions. Its stability under basic conditions and ease of deprotection under acidic conditions make it a valuable intermediate in organic and medicinal chemistry. The dual protection enhances control over synthetic pathways, minimizing side reactions and improving yield. This derivative is particularly useful in solid-phase peptide synthesis (SPPS) and other applications requiring precise amino acid modification.
L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]- structure
88971-40-8 structure
Product Name:L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-
CAS No:88971-40-8
MF:C13H24N2O6
MW:304.339464187622
CID:710634
PubChem ID:2755947
Update Time:2025-05-23

L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]- Chemical and Physical Properties

Names and Identifiers

    • L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-
    • BOC-L-DPA(BOC)-OH
    • Boc-dap(Boc)-OH
    • Boc-Dpr(Boc)-OH
    • Boc-L-Dap(Boc)-OH
    • L-ALANINE,N-[(1,1-DIMETHYLETHOXY)CARBONYL]-3-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]
    • N,N'-di-Boc-2,3-L-Dap-OH
    • N,N'-di-t-boc-(S)-2,3-diaminopropionic acid
    • RARECHEM EM WB 0105
    • N-[(1,1-Dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-L-alanine (ACI)
    • (2S)-2,3-Bis(tert-butoxycarbonylamino)propanoic acid
    • 2,3-Bis((tert-butoxycarbonyl)amino)propionic acid
    • (2S)-2,3-BIS[(TERT-BUTOXYCARBONYL)AMINO]PROPANOIC ACID
    • (2S)-2,3-bis({[(tert-butoxy)carbonyl]amino})propanoic acid
    • AKOS027321180
    • (S)-2,3-Bis((tert-butoxycarbonyl)amino)propanoic acid
    • CS-0099805
    • AS-70407
    • (S)-2,3-Bis((tert-butoxycarbonyl)amino)propanoicacid
    • D,L-N,N'-Di-tert-butoxycarbonyl-2,3-diaminopropionic acid
    • (2S)-2,3-bis[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
    • 88971-40-8
    • SCHEMBL3544394
    • (S)-2,3-bis(tert-butoxycarbonylamino)propanoic acid
    • D76029
    • 3-N-Boc-amino-N-Boc-L-alanine
    • Inchi: 1S/C13H24N2O6/c1-12(2,3)20-10(18)14-7-8(9(16)17)15-11(19)21-13(4,5)6/h8H,7H2,1-6H3,(H,14,18)(H,15,19)(H,16,17)/t8-/m0/s1
    • InChI Key: UDZLUXXCXDIIOK-QMMMGPOBSA-N
    • SMILES: [C@H](C(=O)O)(NC(=O)OC(C)(C)C)CNC(=O)OC(C)(C)C

Computed Properties

  • Exact Mass: 304.16300
  • Monoisotopic Mass: 304.163
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 10
  • Complexity: 394
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.3
  • Topological Polar Surface Area: 114?2

Experimental Properties

  • PSA: 113.96000
  • LogP: 2.27080

L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]- Customs Data

  • HS CODE:2924199090
  • Customs Data:

    China Customs Code:

    2924199090

    Overview:

    2924199090. Other acyclic amides(Including acyclic carbamates)(Including its derivatives and salts). VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, packing

    Summary:

    2924199090. other acyclic amides (including acyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]- Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sulfuric acid Solvents: Ethyl acetate ,  Water ;  cooled
Reference
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Nair, Shrikumar A.; Kolodziej, Andrew F.; Bhole, Gandhali; Greenfield, Matthew T.; McMurry, Thomas J.; et al, Angewandte Chemie, 2008, 47(26), 4918-4921

Production Method 2

Reaction Conditions
1.1 Reagents: Sodium bicarbonate Solvents: 1,4-Dioxane ,  Water ;  4 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Dichloromethane ,  Water ;  pH 2.5
Reference
Tetrahydroimidazo[1,2-a]pyrazine Derivatives: Synthesis and Evaluation as Gαq-Protein Ligands
Kueppers, Jim; Benkel, Tobias ; Annala, Suvi; Kimura, Kenichi; Reinelt, Lisa; et al, Chemistry - A European Journal, 2020, 26(55), 12615-12623

Production Method 3

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: tert-Butanol ,  Water ;  15 °C; 4 h, 15 °C
1.2 Reagents: Potassium bisulfate Solvents: Water ;  pH 2 - 3
Reference
Synthesis and characterization of new first generation dendrimers with high-density amine groups
Jiang, De-hong; Zheng, Hu; Qi, Qing-rong, Huaxi Yaoxue Zazhi, 2010, 25(6), 647-649

Production Method 4

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  15 min, rt
1.2 12 h, rt
Reference
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Dutta, Pradip; Kumari, Smita; Paulraj, Justin; Sharma, Rupali; Vijaykumar, Gonela; et al, New Journal of Chemistry, 2021, 45(23), 10524-10533

Production Method 5

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Acetone ,  Water ;  12 h, rt
Reference
Synthesis and nematicidal activity of piperazinedione derivatives based on the natural product Barettin
Sun, Haiyang; Li, Hui; Wang, Jiayi; Song, Gonghua, Chinese Chemical Letters, 2018, 29(6), 977-980

L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]- Raw materials

L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]- Preparation Products

Additional information on L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-

L-Alanine,N-[(1,1-Dimethylethoxy)Carbonyl]-3-[[(1,1-Dimethylethoxy)Carbonyl]Amino] (CAS No. 88971-40-8)

The compound L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino], also known by its CAS number 88971-40-8, is a significant molecule in the field of synthetic chemistry and biochemistry. This compound is a derivative of L-alanine, a naturally occurring amino acid that plays a crucial role in various biological processes. The introduction of the (1,1-dimethylethoxy)carbonyl group into the structure of L-alanine enhances its chemical properties, making it a valuable intermediate in the synthesis of complex molecules.

L-Alanine is one of the 20 standard amino acids that are essential for protein synthesis. Its structure consists of a central carbon atom bonded to an amino group (-NH2), a carboxyl group (-COOH), a hydrogen atom, and a methyl group (-CH3). The addition of the (1,1-dimethylethoxy)carbonyl group to L-alanine introduces steric hindrance and improves the molecule's stability. This modification is particularly useful in peptide synthesis, where protecting groups like the (1,1-dimethylethoxy)carbonyl group are employed to prevent unwanted side reactions.

The synthesis of L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino] involves multi-step chemical reactions. The process typically begins with the activation of L-alanine using an appropriate coupling agent. The (1,1-dimethylethoxy)carbonyl group is then introduced through a protection reaction. This step ensures that the amino and carboxyl groups are properly shielded during subsequent reactions. The final product is purified using chromatographic techniques to ensure high purity and quality.

In terms of applications, this compound is widely used in peptide synthesis as a building block for constructing more complex molecules. Its protected form allows for precise control over the reaction steps, making it ideal for synthesizing bioactive compounds such as peptides and proteins. Recent studies have highlighted its potential in drug discovery programs targeting various diseases.

Recent research has focused on optimizing the synthesis and application of this compound. For instance, scientists have explored new methods to enhance the efficiency of peptide bond formation using this compound as an intermediate. Additionally, advancements in analytical techniques have enabled better characterization of this compound's physical and chemical properties.

In conclusion, L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino] (CAS No. 88971-40-8) is a vital molecule in modern synthetic chemistry. Its unique structure and versatile applications make it an essential tool for researchers in various fields. As technology continues to evolve, this compound will likely find new uses in drug development and other areas of biotechnology.

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