(2S,3S,4R)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-2,4-dimethylpentanal -Drug Synthesis Database

【结构式】

【分子编号】64637

【品名】(2S,3S,4R)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-2,4-dimethylpentanal

【CA登记号】

【分子式】C₁₃H₂₈O₃Si

【分子量】260.44902

【元素组成】C 59.95% H 10.84% O 18.43% Si 10.78%

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：(XLIX)

Dithiane intermediate (LII). The ozonolysis of the allylic diol (XLVIII) with O3 and PPh3 in dichloromethane/methanol gives the aldehyde (XLIX), which is condensed with propane-1,3-dithiol (L) by means of BF3/OEt2 in dichloromethane to yield the dihydroxylated 1,3-dithiane derivative (LI). Finally, this compound is protected with 3,4-Dmp-CHO (A) and PPTS to afford the desired dithiane intermediate (LII).

参考文献中间体

合成目标

【1】 Smith, A.B.; et al.; The spongistatins: Architecturally complex natural products - Part one: A formal synthesis of (+)-spongistatin 1 by construction of an advanced ABCD fragment. Angew Chem. Int Ed 2001, 40, 1, 191.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	46036	3,4-dimethylbenzaldehyde	5973-71-7	C₉H₁₀O	详情	详情
(XVIII)	64636	(2R,3R,4R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2,4-dimethyl-5-hexen-3-ol		C₁₄H₃₀O₂Si	详情	详情
(XLIX)	64637	(2S,3S,4R)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-2,4-dimethylpentanal		C₁₃H₂₈O₃Si	详情	详情
(L)	29729	1,3-propanedithiol; 3-sulfanylpropylhydrosulfide	109-80-8	C₃H₈S₂	详情	详情
(LI)	64638	(2R,3S,4S)-4-(1,3-dithian-2-yl)-2-methyl-1,3-pentanediol		C₁₀H₂₀O₂S₂	详情	详情
(LII)	64639	(4S,5R)-2-(3,4-dimethylphenyl)-4-[(1S)-1-(1,3-dithian-2-yl)ethyl]-5-methyl-1,3-dioxane		C₁₉H₂₈O₂S₂	详情	详情

Extended Information