تفاعل #565301

ord-5c303ad0276b4530abf8587f28e23270

معادلة التفاعل

OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O
α,β-D-mannopyranose
CC(=O)OC(C)=O
acetic acid anhydride
→
CC(=O)OC[C@H]1OC(OC(C)=O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
above-mentioned title compound
المردود 96.7%
CC(=O)OC[C@H]1OC(OC(C)=O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
1,2,3,4,6-Penta-O-acetyl-α,β-D-mannopyranose
المردود 96.7%

المتفاعلات

—
II
OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O
α,β-D-mannopyranose
CC(=O)OC(C)=O
acetic acid anhydride

الكواشف

لا شيء

المذيبات

—
Carbohydrate
c1ccncc1
pyridine

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىyields

الإجراء التجريبي

Analogously to what is described in the literature [M. L. Wolfrom and A. Thompson in Methods in Carbohydrate Chemistry (R. L. Whistler, M. L. Wolfrom and J. N. BeMiller, Eds.), Academic Press, New York, Vol. II, 53, pp. 211-215, (1963)], the reaction of 150 g (832.5 mmol) of α,β-D-mannopyranose with a mixture that consists of 1500 ml of absolute pyridine and 1500 ml of acetic acid anhydride yields, after working-up, 315 g (96.7%) of the above-mentioned title compound as a crude product in the form of a viscous and colorless oil. By 1H-NMR spectroscopic study of the thus obtained title compound, it was possible to determine the α to β ratio of both anomers at 4:1. Separation of α,β-anomers of the above-mentioned title compound can be eliminated to perform the subsequent reaction step.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US06641797B2uspto-grants-2003_11