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HRID339150

反应详情

EQUATION

反应方程式

HRID 339150 的结构方程式

REACTANTS

反应物

5
结构：c1c[nH]cn1
HCID795

Imidazole

C3H4N2

结构：Cc1cccc(C)n1
HCID7937

2,6-Dimethylpyridine

C7H9N

结构：CC(C)(C)[Si](C)(C)Cl
HCID28928

Chloro(1,1-dimethylethyl)dimethylsilane

C6H15ClSi

结构：C=CC[C@@H](C(=O)OC)[C@H](O)CCOCc1ccccc1
HCID67234162

未命名化合物

结构：C[SiH](C)OC(C)(C)C
HCID71403863

tert-Butoxy(dimethyl)silane

C6H16OSi

PRODUCTS

生成物

1
结构：COC(=O)[C@H](CC=O)[C@@H](CCOCc1ccccc1)O[Si](C)(C)C(C)(C)C
HCID86654300

未命名化合物

收率 88%

AUXILIARIES

试剂、催化剂与溶剂

4
结构：[O]=[Os](=[O])(=[O])=[O]
催化剂HCID30318

Osmium tetroxide

O4Os

结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

结构：CC(C)(C)O
溶剂HCID6386

tert-Butyl alcohol

C4H10O

结构：C1COCCO1.O
溶剂HCID21886435

1,4-Dioxane--water (1/1)

C4H10O3

CONDITIONS

反应条件

温度
25 °C

PROCEDURE

实验过程

The compound obtained in example 3e was protected as the tert-butyl dimethyl silyl ether by treatment with tert-butyldimethylchlorosilane and imidazole in DMF. This compound was treated with 2,6-lutidine and OsO4 2.5% in 2-methyl-2-propanol, followed by NalO4 in 1,4-dioxane-water (3:1) at room temperature. The reaction was stirred at 25° C. for 2 hrs, quenched, and the product purified by chromatography to provide (2R,3R)-5-benzyloxy-3-(tert-butyldimethylsilanyloxy)-2-(2-oxoethyl)pentanoic acid methyl ester in 88% yield.

WORKUP

后处理

  1. customquenched
  2. customthe product purified by chromatography