反应 #1824360

ord-15d7f2a22e2048e09245a2652f7cb420

反应方程式

C=CCO[C@H]1[C@H](O[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](Cl)O[C@@H]2COC(C)=O)O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O
Chloride
C=CCO[C@H]1[C@H](O[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](Cl)O[C@@H]2COC(C)=O)O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O
2,3,6-Tri-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-O-allyl-β-D-galactopyranosyl)-α-D-glucopyranosyl choride
CO
MeOH
→
C=CCO[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](OC)O[C@@H]2CO)O[C@H](CO)[C@H](O)[C@@H]1O
4
收率 67.0%
C=CCO[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](OC)O[C@@H]2CO)O[C@H](CO)[C@H](O)[C@@H]1O
Methyl 4-O-(2-O-allyl-β-D-galactopyranosyl)-β-D-glucopyranoside
收率 67.0%

反应物

C=CCO[C@H]1[C@H](O[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](Cl)O[C@@H]2COC(C)=O)O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O
Chloride
C=CCO[C@H]1[C@H](O[C@H]2[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](Cl)O[C@@H]2COC(C)=O)O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O
2,3,6-Tri-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-O-allyl-β-D-galactopyranosyl)-α-D-glucopyranosyl choride
CO
MeOH
—
50W

试剂

无

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    过滤the suspension was filtered
  2. 2
    其他the filtrate was crystallized from EtOH

实验过程

Chloride 3 (4.4 g, 6.74 mmol) was dissolved in dry MeOH and left at room temperature for two days. The mixture was neutralized with Dowex 50W (H+) resin, the suspension was filtered and the filtrate was crystallized from EtOH to give 4 (1.8 g, 67%), [α]D -1.8° (c 0.2, H2O), m.p. 22-223° C.; 1H NMR (D2O) δ 5.99 (m, 1H, Hc), 5.36 (m, 1H, Hb), 5.28 (m, 1H, Ha), 4.49 (d, 1H, J1',2' =7.9 Hz, H-1'), 4.41 (d, 1H, J1,2 =8.0 Hz, H-1), 4.34 (m, 1H, Hd), 4.26 (m, 1H, He), 3.99 (broad d, 1H, H-6a), 3.83-3.62 (m, 8H, H-3, H-4, H-5, H-6b, H-3', H-5', H-6', H-6'b), 3.58 (s, 3H, Me), 3.4dd, 1H, J2',3' =10.0 Hz, H-2'), 3.32 (m, H-2). Cale'd for C16H28O11 (396.38) C, 48.48; H, 7.12. Found C, 48.47, H, 7.12.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US05962423uspto-grants-1999_10