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HRID25680

反应详情

EQUATION

反应方程式

HRID 25680 的结构方程式

REACTANTS

反应物

1
结构：COc1ccc(Cn2c(=O)ccn([C@@H]3O[C@H]([C@H](O)[C@@H](C(=O)OC(C)(C)C)N(Cc4ccccc4)Cc4ccccc4)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)c2=O)cc1
HCID59065879

未命名化合物

PRODUCTS

生成物

1
结构：COc1ccc(Cn2c(=O)ccn([C@@H]3O[C@H]([C@H](O)[C@H](N)C(=O)OC(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)c2=O)cc1
HCID12137063

未命名化合物

收率 25%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：[Pd]
催化剂HCID23938

Palladium

Pd

结构：CO
溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

tert-Butyl (2S,3R)-3-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl-(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-2-(dibenzylamino)-3-hydroxy-propanoate (3.0 g, 3.33 mmole, obtained from Reference Example 4) was hydrogenated using 10% palladium on carbon (2 g) in methanol (70 ml) under atmospheric pressure. The catalyst was removed, and the volatile was removed in vacuo. The residue was chromatographed (flash column, silica gel, methylene chloride:methanol:diethyl ether=92:4:4) to give the recovered starting material (1.2 g, 50%) and tert-butyl (2S,3R)-2-amino-3-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl-(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-3-hydroxypropanoate (600 mg, 25%) as a white amorphous solid.

WORKUP

后处理

  1. customThe catalyst was removed
  2. customthe volatile was removed in vacuo
  3. customThe residue was chromatographed (flash column, silica gel, methylene chloride:methanol:diethyl ether=92:4:4)