Kaji E, Osa Y, Takahashi K, Zen S
School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
Chem Pharm Bull (Tokyo). 1996 Jan;44(1):15-20. doi: 10.1248/cpb.44.15.
A novel alpha-D-talosaminyl donor, 2-(benzoyloxyimino)-2-deoxy-alpha-D-lyxo-hexopyranosyl bromide has been synthesized in a total yield of 32% over 6 steps from D-galactose. The utility of the donor was evaluated for the elaboration of alpha-D-TalNAc-(1-->6)-alpha-D-Gal, alpha-D-TalNAc-(1-->6)-alpha-D-Glc, and alpha-D-TalNAc-(1-->3)-L-serine derivatives by a simple 3-step sequence, comprising alpha-selective glycosylation of appropriately protected acceptors of D-galactose, D-glucose, and L-serine, talo-selective hydroboration of the oxyimino function to an amino group, and N-acetylation.
一种新型的α-D-塔罗糖胺基供体，即2-(苯甲酰氧基亚氨基)-2-脱氧-α-D-来苏糖己吡喃糖基溴，已从D-半乳糖经6步反应合成，总产率为32%。通过一个简单的三步序列对该供体用于合成α-D-塔罗糖胺-(1→6)-α-D-半乳糖、α-D-塔罗糖胺-(1→6)-α-D-葡萄糖和α-D-塔罗糖胺-(1→3)-L-丝氨酸衍生物的效用进行了评估，该序列包括对D-半乳糖、D-葡萄糖和L-丝氨酸的适当保护的受体进行α-选择性糖基化、将氧亚氨基官能团进行塔罗糖选择性硼氢化转化为氨基以及N-乙酰化。
