1-Bromohexadecane → hexadecyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside

HRID 128202

반응식

HRID 128202 반응식
[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@H:9]([CH3:20])[O:8][C@@H:6]1[SH:7])(=[O:3])[CH3:2].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C(N(CC)CC)C>ClCCl>[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@H:9]([CH3:20])[O:8][C@@H:6]1[S:7][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 82131-BromohexadecaneHCID 8471TriethylamineHCID 232389082,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranose

생성물 1

HCID 22815172hexadecyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside수율 55.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranose (2.0 g, 6.5 mmol) and 1-bromohexadecane (2.0 g, 6.5 mmol) in dichloromethane (40 ml) containing triethylamine (1 ml) is kept under nitrogen for 2 days at room temperature. The reaction is worked up in the usual manner to give a syrup which is put on a silica gel column and eluted with 2-5% ethyl acetate in chloroform. The desired fractions are pooled and concentrated to dryness. Crystallization from aqueous ethanol gives hexadecyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside (1.9 g, 55%), m.p. 49°-50°, [α]D +9° (c, 1.5, chloroform).

후처리

  1. customto give a syrup which
  2. washeluted with 2-5% ethyl acetate in chloroform
  3. concentrationconcentrated to dryness
  4. customCrystallization from aqueous ethanol

출처 및 근거

ORD 기록
ord-07c5a7bbf3e042ecad9e6da09d899969
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04259324

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