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HRID1862753

反应详情

EQUATION

反应方程式

HRID 1862753 的结构方程式

REACTANTS

反应物

4
结构：CCOCC.FB(F)F
HCID8000

Ethane, 1,1'-oxybis-, compd. with trifluoroborane (1:1)

C4H10BF3O

结构：Cc1ccccc1S
HCID8712

2-Methylbenzenethiol

C7H8S

结构：CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](NC(=O)OCC(Cl)(Cl)Cl)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
HCID11038656

未命名化合物

结构：CC(=O)OC[C@H]1O[C@H](Sc2ccc(C)cc2)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
HCID11775389

未命名化合物

PRODUCTS

生成物

1
结构：CC(=O)OC[C@H]1O[C@@H](Sc2ccc(C)cc2)[C@H](NC(=O)OCC(Cl)(Cl)Cl)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
HCID15497894

未命名化合物

收率 89%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：ClCCl
溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

The tittle compound was prepared from 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxylcarbonylamino)-β-D-glucopyranose (Boullanger, P. et al Carbohydr. Res. 1990, 202, 151) (11.8 g, 22.5 mmol), thiocresol (3.07 g, 24.75 mmol) and BF3-Et2O (10 mL) in dry CH2Cl2 (60 mL) by the procedure described above (see compound 1) The crude product was crystallization from ether to give 21 (11.8 g, 89%) as white crystals: m.p. 175-176° C.; [α]D22 +3° (c, 0.5, CHCl3); 1H-NMR (400 MHz, CDCl3) δ 2.00 (s, 3H), 2.01 (s, 3H), 2.09 (s, 3H), 2.35 (s, 3H), 3.71-3.73 (m, 1H), 4.11-4.25 (m, 2H), 4.73 (d, 1H, J=12.0 Hz), 4.79 (d, 1H, J=10.8 Hz), 5.01 (t, 1H, J=9.8 Hz), 5.26 (d, 1H, J=9.8 Hz), 5.31 (d, 1H, J=9.1 Hz), 7.11 (d, 2H, J=8.0 Hz), 7.41 (d, 2H, J=8.0 Hz); 13C-NMR (400 MHz, CDCl3); δ 20.56, 20.61, 20.73, 21.15, 54.93, 62.25, 68.44, 73.14, 74.47, 75.70, 86.65, 95.36, 127.84, 129.71, 133.62, 138.70, 153.85, 169.45, 170.61; HRMS for C22H26NO9SCl3Na (M+Na) calcd 610.0266, found 610.0286. Anal. Calcd for C22H26NO9SCl3: C, 45.03; H, 4.47; N, 2.39. Found: C, 45.46; H, 4.26; N, 2.30.

WORKUP

后处理

  1. customcrystallization from ether