Stearic Acid → C18-Ceramide

HRID 468224ノート

反応式

HRID 468224 の反応式
[OH:1][CH2:2][C@@H:3]([C@@H:5](/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[OH:6])[NH2:4].CCN=C=NCCCN(C)C.[C:33](O)(=[O:51])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:33]([NH:4][C@H:3]([C@H:5]([OH:6])/[CH:7]=[CH:8]/[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:2][OH:1])(=[O:51])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]

参加物

6

反応物 3

HCID 5281Stearic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 5280335Sphingosine

生成物 1

HCID 5283565C18-Ceramide収率 75%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of sphingosine (100 mg, 0.33 mmol) in CH2Cl2 (3 mL) was added EDCI (128 mg, 0.66 mmol) and DMAP (cat.). Under stirring, stearic acid (95 mg, 0.33 mmol in 10 mL CH2Cl2) was added dropwise over a period time of 16 h. The reaction was stirred under argon for 24 h at rt. Solvent was evaporated and the residue was applied to silica gel column chromatography (CHCl3:MeOH=9:1, Rf=0.43) to afford 8 as a white powder (140 mg, 75%). 1H NMR (600 MHz, CDCl3) δ 0.88 (t, J=6.8 Hz, 6H), 1.26-1.40 (m, 50H), 1.64 (t, J=7.2 Hz, 2H), 2.06 (dd, J=14.4, 7.2 Hz, 2H), 2.24 (t, J=7.2 Hz, 2H), 3.71 (m, 1H), 3.91-3.97 (m, 2H), 4.32 (m, 1H), 5.42 (dd, J=15.6, 6.6 Hz, 1H), 5.79 (dt, J=15.6, 6.6 Hz, 1H), 6.28 (d, J=7.2 Hz, 1H). 13C NMR (150 MHz, CDCl3) δ 14.3, 22.9, 26.0, 29.4, 29.5, 29.6, 29.7, 29.8, 29.9, 32.2, 32.6, 54.7, 62.8, 74.9, 129.0, 134.6, 174.2. ESIMS calc'd for C36H71NNaO3 [M+Na]+ 588.53. found: 588.18.

後処理

  1. stirringThe reaction was stirred under argon for 24 h at rt
  2. customSolvent was evaporated

出典と根拠

ORDレコード
ord-538136b6a2d84d62a4c62c8bcb36a263
出典データセット
uspto-grants-2014_01
特許番号
US08624006B2

反応ノート

読み込み中…