(2S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoic acid

• ChemBase编号: 69916
• 分子式: C11H13NO5
• 平均质量: 239.22462
• 单一同位素质量: 239.07937252
• SMILES: C(=O)([C@@H](NC(=O)OCc1ccccc1)CO)O
• Canonical SMILES: OC[C@@H](C(=O)O)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C11H13NO5/c13-6-9(10(14)15)12-11(16)17-7-8-4-2-1-3-5-8/h1-5,9,13H,6-7H2,(H,12,16)(H,14,15)/t9-/m0/s1
• InChIKey: GNIDSOFZAKMQAO-VIFPVBQESA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoic acid
• IUPAC传统名: (2S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoic acid
• 别名: N-苄氧羰基-L-丝氨酸; Z-L-丝氨酸; 苄氧羰基-L-丝氨酸; Carbobenzyloxy-L-serine; Z-L-Serine; N-Cbz-L-serine; N-Benzyloxycarbonyl-L-serine; Z-Ser-OH; (2S)-2-[(Benzyloxycarbonyl)amino]-3-hydroxypropanoic Acid; Benzyloxycarbonyl-L-serine; N-(Benzyloxycarbonyl)-L-serine; N-Carbobenzoxy-L-serine; N-Carbobenzyloxy-L-serine; N-[(Phenylmethoxy)carbonyl]serine; NSC 286604; N-Carboxy-L-serine N-Benzyl Ester; Z-Ser-OH; N-Cbz-L-Serine

登记号

• CAS号: 1145-80-8
• EC号: 214-546-4
• MDL号: MFCD00002662
• Beilstein号: 2058314
• PubChem SID: 24888517; 162035641
• PubChem CID: 100310

理论计算性质

• Acid pKa: 3.5838287
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): -1.3739644
• LogD (pH = 7.4): -2.8116252
• Log P: 0.53698957
• 摩尔折射率: 57.721 cm^3
• 极化性: 22.675972 Å^3
• 极化表面积: 95.86 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 116-119 °C; 116-119 °C(lit.); 117-120°C
• 比旋光度: [α]20/D +5.8°, c = 2.7 in acetic acid; [α]20/D +6.0±0.5°, c = 7% in acetic acid; +6 (c=7 in acetic acid)

安全信息

• 保存注意事项: IRRITANT
• 德国WGK号: 3
• TSCA收录: false; 否
• 保存温度: -20°C

产品相关信息

• 纯度: ≥99%; ≥99.0% (T); 95+%; 99%
• 级别: puriss.
• 线性分子式: HOCH2CH(NHCO2CH2C6H5)CO2H

详细说明

Sigma Aldrich - C5252

Application
肽合成的结构单元；通过 β-内酯合成各种 α-氨基酸的原料1

Sigma Aldrich - 860700

Application
肽合成的结构单元；通过 β-内酯合成各种 α-氨基酸的原料1
包装
25 g in poly bottle

Sigma Aldrich - 97190

Application
肽合成的结构单元；通过 β-内酯合成各种 α-氨基酸的原料1

Toronto Research Chemicals - C182415

Building block in peptide synthesis.

参考文献

• Pansare, S. V.; Org. Synth. 70, 10(1992)
• Mitsunobu conversion to the ?-lactone and subsequent reaction with pyrazole is an example of a versatile route to N-protected ɑ-amino acids: Org. Synth. Coll., 9, 58 (1998) and references therein:
  
• For a different synthesis of racemic pyrazoloaniline, see 2-Acetamidoacrylic acid, L01649.