تفاعل #6141

ord-d279cfea5adb4eb4852a26d5438186a3

معادلة التفاعل

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1
3-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
C[O-].[Na+]
sodium methylate
→
N#Cc1cccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c1
expected product
المردود 85.0%
N#Cc1cccc(O[C@@H]2SC[C@@H](O)[C@H](O)[C@H]2O)c1
3-cyanophenyl 5-thio-β-D-xylopyranoside
المردود 85.0%

المتفاعلات

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1
3-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
—
solution
C[O-].[Na+]
sodium methylate

الكواشف

لا شيء

المذيبات

CO
methanol
CO
methanol

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىIf the procedure described in Preparation LXXXIV

الإجراء التجريبي

If the procedure described in Preparation LXXXIV is followed starting from 2.12 g (5.4.10-3 mol) of 3-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside and 0.2 ml of a solution of sodium methylate in methanol (8% w/v of Na), reacted in 60 ml of methanol for 30 min, 1.22 g (yield: 85%) of the expected product are obtained after precipitation in ether and lyophilization.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05246961uspto-grants-1993_09