Benzene → Octyl 2,6-di-O-benzoyl-4-O-(4-O-acetyl-2,6-di-O-benzoyl-beta-D-galacto-pyranosyl)-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-beta-D-glucopyranoside

HRID 2627

反応式

HRID 2627 の反応式
[C:1]([O:9][C@@H:10]1[C@@H:24]([O:25][C@@H:26]2[O:55][C@@H:54]([CH3:56])[C@@H:45]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C@@H:36]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:27]2[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:23]([O:57][C@@H:58]2[O:74][C@H:73]([CH2:75][O:76][C:77](=[O:84])[C:78]3[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=3)[C@H:71]([OH:72])[C@H:69]([OH:70])[C@H:59]2[O:60][C:61](=[O:68])[C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[C@@H:22]([CH2:85][O:86][C:87](=[O:94])[C:88]2[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=2)[O:21][C@H:11]1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC=CC=1.C([C:103](CC)(CC)[C:104]([O-])([O-])[O-:105])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(N(CC)CC)C>[C:1]([O:9][C@@H:10]1[C@@H:24]([O:25][C@@H:26]2[O:55][C@@H:54]([CH3:56])[C@@H:45]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C@@H:36]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C@@H:27]2[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:23]([O:57][C@@H:58]2[O:74][C@H:73]([CH2:75][O:76][C:77](=[O:84])[C:78]3[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=3)[C@H:71]([O:72][C:104](=[O:105])[CH3:103])[C@H:69]([OH:70])[C@H:59]2[O:60][C:61](=[O:68])[C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[C@@H:22]([CH2:85][O:86][C:87](=[O:94])[C:88]2[CH:89]=[CH:90][CH:91]=[CH:92][CH:93]=2)[O:21][C@H:11]1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 21875354TriethylorthoaceateHCID 22868661Octyl 2,6-di-O-benzoyl-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-4-O-(2,6-di-O-benzoyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside

生成物 1

HCID 22868663Octyl 2,6-di-O-benzoyl-4-O-(4-O-acetyl-2,6-di-O-benzoyl-beta-D-galacto-pyranosyl)-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-beta-D-glucopyranoside収率 91.3%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

Compound 22 (5 g) was dissolved a 1:1 mixture of benzene and triethylorthoacetate (110 mL), containing 4-toluenesulfonic acid (0.2 g), and the mixture was stirred for 1 h at room temperature. The acid was neutralized with triethylamine, and the mixture evaporated to dryness. The residue was dissolved in 80% aqueous acetic acid (75 mL) and stirred for 40 min at room temperature. The acetic acid was evaporated under diminished pressure and the last traces were removed by co-evaporation with toluene to yield 23 (4.7 g, 91.3%); [α]D, -4.5° (c 0.8, chloroform), t.l.c. (5:1 ethyl acetate-toluene). 13C NMR (CDCl3): δ170.98 (COCH3), 166.75, 166.33, 166.18, 165.07 (4×PhCO), 102.03, 101.08 (C-1, C-1'), 98.16 (C-1 fuc), 80.07, 78.23 (C-3, C-4), 74.69, 73.53, 73.24 (3×PhCH2), 70.66 [OCH2 (CH2)6 ], 63.23, 61.42 (C-6, C-6'), 32.25-23.14 [(CH2)6CH3 ], 21.20 (COCH3), 17.49 (C-6 fuc), and 14.63 (CH3).

後処理

  1. customthe mixture evaporated to dryness
  2. dissolutionThe residue was dissolved in 80% aqueous acetic acid (75 mL)
  3. stirringstirred for 40 min at room temperature
  4. customThe acetic acid was evaporated under diminished pressure
  5. customthe last traces were removed by co-evaporation with toluene

出典と根拠

ORDレコード
ord-794405d5658443eaa2988d9f4b124f36
出典データセット
uspto-grants-1998_03
特許番号
US05728685

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