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【结 构 式】

【分子编号】65657

【品名】 

【CA登记号】 

【 分 子 式 】C19H31O4

【 分 子 量 】323.45274

【元素组成】C 70.55% H 9.66% O 19.79%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XV)

The C1-C6 building block (V) (segment A) can be obtained as follows. Protection of (–)-pantolactone (X) as the tetrahydropyranyl ether (XI) using dihydropyran and pyridinium tosylate, followed by reduction of the lactone ring with DIBAL in cold toluene, gives the lactol (XII). Subsequent Wittig reaction of the cyclic hemiacetal (XII) with methylene triphenylphosphorane affords the hydroxy olefin (XIII), which is protected as the benzyl ether (XIV) by treatment with benzyl bromide and potassium tert-butoxide. Hydroboration of olefin (XIV) followed by quenching with alkaline H2O2 provides the primary alcohol (XV) as the major isomer, which is converted to the acetonide (XVI) by treatment with 2,2-dimethoxypropane and p-toluenesulfonic acid. After catalytic hydrogenolysis of the benzyl ether (XVI), the deprotected alcohol (XVII) is oxidized to aldehyde (XVIII) under Swern conditions. Then, addition of 3-butenylmagnesium bromide (XIX) to the aldehyde (XVIII) provides alcohol (XX), which is oxidized to the target ketone (V) by treatment with N-methylmorpholine N-oxide and a catalytic amount of tetrapropylammonium perruthenate (3). Scheme 2.

3 Klar, U., Rohr, B., Kuczynski,F., Schwede, W., Berger, M., Skuballa, W., Buchmann, B. Efficient chiral pool synthesis of the C1-C6 fragment of epothilone. Synthesis 2005, (2): 301-5.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 65648     C14H24O3 详情 详情
(X) 51427 D-Pantolactone; R(-)-2-Hydroxy-3,3-dimethyl-gamma-butyrolactone 599-04-2 C6H10O3 详情 详情
(XI) 65653     C11H19O4 详情 详情
(XII) 65654     C11H21O4 详情 详情
(XIII) 65655     C12H23O3 详情 详情
(XIV) 65656     C19H28O3 详情 详情
(XV) 65657     C19H31O4 详情 详情
(XVI) 65658     C17H26O3 详情 详情
(XVII) 65659     C10H20O3 详情 详情
(XVIII) 65660     C10H18O3 详情 详情
(XIX) 35896 bromo(3-butenyl)magnesium 7103-09-5 C4H7BrMg 详情 详情
(XX) 65661     C14H26O3 详情 详情
Extended Information