تفاعل #83107

ord-4157e3b36b154ed298b12651e76816a0

معادلة التفاعل

CC(C)(C)[Si](OC[C@@H]1CCC(O)S1)(c1ccccc1)c1ccccc1
5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranose
CC(O)=S
thioacetic acid
Cc1ccccc1S(=O)(=O)O
toluenesulfonic acid
→
CC(=O)[SH]1C(O)CC[C@H]1CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C
desired product
المردود 67.1%
CC(=O)[SH]1C(O)CC[C@H]1CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C
1-S-Acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranose
المردود 67.1%

المتفاعلات

CC(C)(C)[Si](OC[C@@H]1CCC(O)S1)(c1ccccc1)c1ccccc1
5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranose
CC(O)=S
thioacetic acid
Cc1ccccc1S(=O)(=O)O
toluenesulfonic acid

الكواشف

لا شيء

المذيبات

ClCCl
methylene chloride

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىflash chromatographed on silica gel

الإجراء التجريبي

Two grams of 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thioribofuranose (prepared according to J. A. Secrist et al., J. Med. Chem., 1992,35,533) is stirred with 0.456 g of thioacetic acid in 25 ml of methylene chloride and 0.0.025 g of toluenesulfonic acid for 68 hours. On workup the reactiion is adsorbed onto magnesium silicate and then flash chromatographed on silica gel to give 1.5 g of the desired product.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05623081uspto-grants-1997_04