Boc-D-Phe-OH | Amino Acid Derivatives

Boc-D-Phe-OH is a protected D-phenylalanine derivative with the amino group protected by tert-butoxycarbonyl (Boc), used for constructing D-phenylalanine residues.

Synonyms: Boc-D-Phe-OH

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Quality Control of Boc-D-Phe-OH Purity: 98% SDS Specification

COA

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NMR

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CNMR

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HPLC

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LC-MS

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Product Details of Boc-D-Phe-OH

CAS No. :	18942-49-9
Formula :	C₁₄H₁₉NO₄
M.W :	265.31
SMILES Code :	[H][C@](CC1=CC=CC=C1)(NC(=O)OC(C)(C)C)C(O)=O
Synonyms :	Boc-D-Phe-OH
MDL No. :	MFCD00063149
InChI Key :	ZYJPUMXJBDHSIF-LLVKDONJSA-N
Pubchem ID :	637610

Safety of Boc-D-Phe-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of Boc-D-Phe-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 18942-49-9 ]

[ 18942-49-9 ] Synthesis Path-Downstream 1~35

1
[ 18942-49-9 ]
[ 29390-67-8 ]
[ 122855-45-2 ]

References: [1]Tetrahedron Asymmetry,1990,vol. 1,p. 367 - 370.

2
[ 18942-49-9 ]
[ 18650-39-0 ]
[ 172422-78-5 ]

References: [1]Tetrahedron,1995,vol. 51,p. 11235 - 11250.

3
[ 18942-49-9 ]
[ 104091-08-9 ]
[ 590-86-3 ]
3-[(2R,5R)-5-Benzyl-1-(3-methyl-butyl)-3,6-dioxo-piperazin-2-yl]-propionic acid [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 6573 - 6593.

4
[ 13836-37-8 ]
[ 84624-27-1 ]
[ 18942-49-9 ]
[ 47355-10-2 ]
N^α-Boc-His(N^ϖ-Bom), N^α-Boc-Asp(N^β-Fmo) [ No CAS ]
[ 137668-62-3 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 118 - 123.

5
[ 13836-37-8 ]
[ 84624-27-1 ]
[ 18942-49-9 ]
[ 47355-10-2 ]
N^α-Boc-His(N^ϖ-Bom), N^α-Boc-Asp(N^β-Fmo), acetic ahydride [ No CAS ]
[ 137668-63-4 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 118 - 123.

6
[ 13836-37-8 ]
[ 84624-27-1 ]
[ 18942-49-9 ]
[ 47355-10-2 ]
N^α-Boc-His(N^ϖ-Bom), N^α-Boc-Asp(N^β-Fmo), hexanoic acid [ No CAS ]
[ 137668-64-5 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 118 - 123.

7
[ 13836-37-8 ]
[ 84624-27-1 ]
[ 18942-49-9 ]
[ 47355-10-2 ]
N^α-Boc-His(N^ϖ-Bom), N^α-Boc-Asp(N^β-Fmo), decanoic acid [ No CAS ]
[ 137668-65-6 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 118 - 123.

8
[ 13836-37-8 ]
[ 84624-27-1 ]
[ 18942-49-9 ]
[ 47355-10-2 ]
N^α-Boc-His(N^ϖ-Bom), N^α-Boc-Asp(N^β-Fmo), myristic acid [ No CAS ]
[ 137668-66-7 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 118 - 123.

9
[ 13836-37-8 ]
[ 84624-27-1 ]
[ 18942-49-9 ]
[ 47355-10-2 ]
N^α-Boc-His(N^ϖ-Bom), N^α-Boc-Asp(N^β-Fmo), palmitoyl chloride [ No CAS ]
[ 137668-67-8 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 118 - 123.

10
[ 4530-20-5 ]
[ 13836-37-8 ]
[ 18942-49-9 ]
[ 47355-10-2 ]
N^im-Tos-His, N^α-Boc-γ-Bzl-Glu, N^α-Boc-Nle, N-acetylimidazole [ No CAS ]
[ 82263-58-9 ]

References: [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1022 - 1027.

11
[ 13836-37-8 ]
[ 84624-27-1 ]
[ 18942-49-9 ]
[ 47355-10-2 ]
N^α-Boc-His(N^ϖ-Bom), N^α-Boc-Asp(β-Fmo), N^α-Boc-Nle, Ac2O [ No CAS ]
[ 121062-08-6 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2555 - 2561.

12
[ 18942-49-9 ]
Fmoc-D-Trp(Boc)-OHFmoc-Val-OH [ No CAS ]
[ 38675-10-4 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1984 - 2008.

13
[ 18942-49-9 ]
[ 38675-10-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 45 - 49.
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 226 - 231.
[3]Journal of Medicinal Chemistry,1993,vol. 36,p. 314 - 319.
[4]Journal of Medicinal Chemistry,2016,vol. 59,p. 7576 - 7583.
[5]Patent: WO2017/21004,2017,A1 .
[6]Cell Chemical Biology,2021,vol. 28,p. 221 - 7,227.

14
[ 18942-49-9 ]
[ 17664-93-6 ]
[ 1024829-63-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃;	These syntheses were carried out according to the scheme shown in FIG. 4. The intermediates described below correspond to those shown in FIG. 4. To a suspension of Boc-D-Phe-OH intermediate I-1 (7.96 g, 30.0 mmol), D-Leu-OBn p-TsOH intermediate I-2 (11.80 g, 30.0 mmol), HOBt monohydrate (4.46 g, 33.0 mmol) and DIEA (8.53 g, 66.0 mmol) in anhydrous THF (250 mL) cooled in an ice-water bath was added EDCI (6.33 g, 33.0 mmol) in four portions over 20 minutes with 5 minutes between each addition. The suspension was stirred overnight from a starting temperature of 0 C. to room temperature. After evaporation of THF, the residue was dissolved in ethyl acetate and washed sequentially with 10% citric acid, saturated NaHCO3 and water. The organic phase was dried over sodium sulfate and evaporated under reduced pressure. The residue was dissolved in DCM, passed through a silica gel plug and eluted with 20% ethyl acetate in hexanes. The eluant was evaporated to give the pure product, Boc-D-Phe-D-Leu-OBn, intermediate I-3 (12.40 g, 88%) as a clear oil. LC-MS: m/z=469 (M+H).; FIG. 4: General scheme used in the synthesis of compounds (25)-(37). Steps a-h were carried out with the following reactants or conditions: a) EDCI, HOBt, DIEA, THF; b) TFA, DCM; c) Boc-D-Phe-OH, EDCI, HOBt, DIEA; d) H2, Pd/C; e) D-Lys(Boc)-OAll, TBTU, DIEA, DMF; f) Pd(PPh3)4, pyrrolidine; g) HNRaRb, HBTU; h) HCl, dioxane.

References: [1]Patent: US7402564,2008,B1 .Location in patent: Page/Page column 6; 63; sheet 4.

15
Fmoc-D-allo-MeIle-OH [ No CAS ]
[ 35661-60-0 ]
[ 18942-49-9 ]
[ 109425-51-6 ]
[ 104091-08-9 ]
calpinactam [ No CAS ]