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HRID1486462

反应详情

EQUATION

反应方程式

HRID 1486462 的结构方程式

REACTANTS

反应物

2
结构：NC(N)=S
HCID2723790

Thiourea

CH4N2S

结构：CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
HCID2734143

α-Acetobromogalactose

C14H19BrO9

PRODUCTS

生成物

1
结构：CC(=O)OC[C@H]1O[C@@H](SC(N)=[NH2+])[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O.[Br-]
HCID86698937

未命名化合物

收率 91%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC(C)=O
溶剂HCID180

Acetone

C3H6O

CONDITIONS

反应条件

温度
20 °C

PROCEDURE

实验过程

2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (6; 15.00 g, 36.48 mmol) and thiourea (3.05 g, 40.07 mmol) were dissolved in acetone (75 mL). The solution was heated to reflux for 2 hours, and subsequently filtered and cooled to 20° C. Addition of pentane (75 mL) resulted in the precipitation of the product as a white, crystalline solid (16.11 g, 91%). 1H-NMR (400 MHz, [D6]DMSO,): δ=1.95 (s, 3H, CH3), 2.01 (s, 3H, CH3), 2.08 (s, 3H, CH3), 2.14 (s, 3H, CH3), 4.09 (m, 2H, H6, H6′), 4.45 (t, J=6.4 Hz, 1H, H5), 5.11 (t, J2,3=10 Hz, 1H, H2), 5.22 (dd, J2,3=9.9 Hz, J3,4=3.2 Hz, 1H, H3), 5.39 (d, J=3.2 Hz, 1H, H4), 5.71 (d, J1,2=10 Hz, 1H, H1), 9.11 (br, 2H, NH2), 9.35 (br, 2H, NH2).

WORKUP

后处理

  1. temperatureThe solution was heated
  2. temperatureto reflux for 2 hours
  3. filtrationsubsequently filtered
  4. additionAddition of pentane (75 mL)