(2R)-5-methyl-5-hexene-1,2-diol -Drug Synthesis Database

【结构式】

【分子编号】52831

【品名】(2R)-5-methyl-5-hexene-1,2-diol

【CA登记号】

【分子式】C₇H₁₄O₂

【分子量】130.18696

【元素组成】C 64.58% H 10.84% O 24.58%

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：(III)

The chiral cyclohexenone intermediate (VII) was prepared as follows. Epoxide ring opening of (S)-glycidol (I) with the Grignard reagent (II) produced diol (III), which was protected as the isopropylidene ketal (IV) by treatment with 2,2-dimethoxypropane. Addition of bromine to olefin (IV) and further cyclization of the resultant dibromide in the presence of potassium hexamethyldisilazide gave rise to the spiro cyclopentene (V). Ozonolysis of (V), followed by reductive work-up, yielded the keto aldehyde (VI), which upon treatment with KOH underwent intramolecular aldol condensation to the target cyclopentenone (VII).

参考文献中间体

合成目标

【1】 Taber, D.F.; et al.; Synthesis of (-)-fumagillin. J Am Chem Soc 1999, 121, 23, 5589.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	19241	(2S)oxiranylmethanol	60456-23-7	C₃H₆O₂	详情	详情
(II)	52830	2-Methylallylmagnesium chloride		C₄H₇ClMg	详情	详情
(III)	52831	(2R)-5-methyl-5-hexene-1,2-diol		C₇H₁₄O₂	详情	详情
(IV)	52832	(4R)-2,2-dimethyl-4-(3-methyl-3-butenyl)-1,3-dioxolane		C₁₀H₁₈O₂	详情	详情
(V)	52833	(5S)-2,2,7-trimethyl-1,3-dioxaspiro[4.4]non-6-ene		C₁₀H₁₆O₂	详情	详情
(VI)	52834	(4R)-2,2-dimethyl-4-(3-oxobutyl)-1,3-dioxolane-4-carbaldehyde		C₁₀H₁₆O₄	详情	详情
(VII)	52835	(5S)-2,2-dimethyl-1,3-dioxaspiro[4.5]dec-6-en-8-one		C₁₀H₁₄O₃	详情	详情

Extended Information