1,1-dimethoxycyclohexane; 1-methoxycyclohexyl methyl ether -Drug Synthesis Database

【结构式】

【分子编号】42385

【品名】1,1-dimethoxycyclohexane; 1-methoxycyclohexyl methyl ether

【CA登记号】933-40-4

【分子式】C₈H₁₆O₂

【分子量】144.21384

【元素组成】C 66.63% H 11.18% O 22.19%

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：(XIX)

Synthesis of intermediate (XX): The oxidation of silylated diol (XV) with OsO4, Pb(OAc)4 and N-methylmorpholine-N-oxide (NMO) in acetone/benzene gives the aldehyde (XVI), which is condensed with formaldehyde by means of KOtBu and B-iodo-9-borabicyclo[3.3.1]nonane (B-I-9-BBN) to yield the iodovinyl compound (XVII). The desilylation of (XVII) with HF and pyridine in THF affords the diol (XVIII), which is treated with 1,1-dimethoxycyclohexane (XIX) and pyridinium p-toluenesulfonate (PPTS) to provide the desired intermediate (XX).

参考文献中间体

合成目标

【1】 Guo, J.; et al.; Total synthesis of altohyrtin A (spongistatin 1): Part 1. Angew Chem. Int Ed Engl 1998, 37, 1-2, 187.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XV)	42381	(5S,6R)-2,2,3,3,6,9,9,10,10-nonamethyl-5-[(1R)-1-methyl-2-propenyl]-4,8-dioxa-3,9-disilaundecane; tert-butyl(dimethyl)silyl (2R,3S,4R)-3-[[tert-butyl(dimethyl)silyl]oxy]-2,4-dimethyl-5-hexenyl ether		C₂₀H₄₄O₂Si₂	详情	详情
(XVI)	42382	(3R,4S,5R)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethylhexanal		C₂₀H₄₄O₃Si₂	详情	详情
(XVII)	42383	tert-butyl(dimethyl)silyl (2R,3R,4S)-3-[[tert-butyl(dimethyl)silyl]oxy]-5-iodo-2,4-dimethyl-5-hexenyl ether; (5R,6R)-5-[(1S)-2-iodo-1-methyl-2-propenyl]-2,2,3,3,6,9,9,10,10-nonamethyl-4,8-dioxa-3,9-disilaundecane		C₂₀H₄₃IO₂Si₂	详情	详情
(XVIII)	42384	(2R,3R,4S)-5-iodo-2,4-dimethyl-5-hexene-1,3-diol		C₈H₁₅IO₂	详情	详情
(XIX)	42385	1,1-dimethoxycyclohexane; 1-methoxycyclohexyl methyl ether	933-40-4	C₈H₁₆O₂	详情	详情
(XX)	42386	(2R,3R)-2-[(1S)-2-iodo-1-methyl-2-propenyl]-3-methyl-1,5-dioxaspiro[5.5]undecane		C₁₄H₂₃IO₂	详情	详情

Extended Information