Triethylamine → HCID 86624083, 화합물

HRID 548515노트

반응식

HRID 548515 반응식
Cl.[OH:2][CH:3]1[O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]([OH:7])[C@@H:4]1[NH2:5].C(N([CH2:19][CH3:20])CC)C>CN(C=O)C>[C:3]([NH:5][C@H:4]1[C@@H:6]([OH:7])[C@H:8]([OH:9])[C@@H:10]([CH2:12][OH:13])[O:11][CH:3]1[OH:2])(=[O:2])[CH2:4][CH2:6][C:19]#[CH:20]

참가 물질

4

반응물 2

HCID 8471TriethylamineHCID 9964480(3S,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

생성물 1

HCID 86624083HCID 86624083, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of D-mannosamine hydrochloride (863 mg, 4.0 mmol), N-succinimidyl 4-pentynoate 9 (Salmain M, Vessieres A, Butler I S, Jaouen G (1991) Bioconjug Chem 2:13-15.) (781 mg, 4.0 mmol), triethylamine (1.67 ml, 12.0 mmol) in DMF (31 ml) was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, and the residue was purified by flash column chromatography (CHCl3/MeOH 8:1) to give N-4-Pentynoylmannosamine, 10 (898 mg, 87%); 1H-NMR (500 MHz, D2O)□ 2.37 (t, 2.63H, J=2.5 Hz), 2.48-2.63 (m, 10.5H), 3.38-3.42 (m, 1H), 3.52 (t, 1H, J=10 Hz), 3.63 (t, 1.63H, J=10 Hz), 3.69-3.91 (m, 7.89H), 4.05 (dd, 1.63H, J=4.5 and 10 Hz), 4.35 (dd, 1.63H, J=1.5 and 4.5 Hz), 4.47 (dd, 1H, J=1.5 and 4.5 Hz), 5.03 (d, 1H, J=1.5 Hz), 5.13 (d, 1.63H, J=1.5 Hz); 13C-NMR (125 MHz, D2O)□ 14.78, 14.91, 34.62, 34.79, 53.67, 54.50, 60.91, 60.93, 67.01, 67.28, 69.25, 70.56, 70.71, 72.47, 72.50, 76.80, 84.04, 84.45, 93.36, 93.67, 175.68, 176.41; ESI-TOF-HRMS m/e calculated for (M+H)+ C11H17NO6 260.1129; found 260.1120.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash column chromatography (CHCl3/MeOH 8:1)

출처 및 근거

ORD 기록
ord-abfb9f7fb1894b788c52791baae0e35f
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943330B2

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