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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 23, Number 1
JKCSEZ 23(1)
February 20, 1979 

The Efficient Synthesis of 6-O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-D-galactopyranose and Its Derivatives

6-O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-D-galactopyranose 및 유도체의 합성
Bong Young Chung, Young Key Sim

정봉영, 심영기
Silver triflate와 syn-collidine 존재하에서 3,4,6-tri-O-acetyl-2-phthalimido-β-D-glucopyranosyl bromide (2)와 1,2;3,4-di-O-isopropylidene-α-D-galactopyranose (3)를 반응시켜 1,2;3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-galactopyranose (4)를 86%의 수득률로 얻었다. 화합물 4를 hydrazine과 작용시켜 phthalimido기와 acetyl기를 동시에 제거한후, 다시 acetyl화하고 isopropylidene기와 O-acetyl기를 가수분해하면 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-D-galactopyranose (1)가 총수득율 65.8%로 얻어졌다. 또한 화합물 4를 변형시켜 특정위치에 hydroxyl기를 가진 몇 가지 유도체도 합성하였다.

Condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (2) with 1,2;3,4-di-O-isopropylidene-α-D-galactopyranose (3) in the presence of silver triflate and syn-collidine gave 1,2;3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-galactopyranose (4) in 86% yield. Cleavage of phthalimido group and de-O-acetylation with hydrazine, acetylation, and hydrolysis of isopropylidene and O-acetyl groups furnished 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-D-galactopyranose (1) with overall yield of 65.8 % starting from 3. Some other derivatives of 1 which have free hydroxyl groups at the specific position have also been prepared from 4. These compounds could be used as precursors for further glycosidation reactions.

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