(5S)-4-[2-(1,3-dioxolan-2-yl)-6-(methoxymethoxy)phenyl]-2,8,10,10-tetramethyl-9-[(E)-(phenylsulfanyl)methylidene]-1,3-dioxa-2-boraspiro[4.5]dec-7-en-7-yl triisopropylsilyl ether -Drug Synthesis Database

【结构式】

【分子编号】27207

【品名】(5S)-4-[2-(1,3-dioxolan-2-yl)-6-(methoxymethoxy)phenyl]-2,8,10,10-tetramethyl-9-[(E)-(phenylsulfanyl)methylidene]-1,3-dioxa-2-boraspiro[4.5]dec-7-en-7-yl triisopropylsilyl ether

【CA登记号】

【分子式】C₃₈H₅₅BO₇SSi

【分子量】694.813

【元素组成】C 65.69% H 7.98% B 1.56% O 16.12% S 4.62% Si 4.04%

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：(IV)

The reaction of the chiral hydroxyaldehyde (I) with the phenyllithium derivative (II) gives the condensation product (III), which is protected with methylboronic acid yielding the cyclic boronate (IV). The cyclization of (IV) by means of TiCl4 followed by a treatment with HF affords the tricyclic tetrol (V), which is finally selectively benzoylated with benzoic acid and DCC to give the target monobenzoate.

参考文献中间体

合成目标

【1】 Morihira, K.; Nishimori, T.; Kusama, H.; Horiguchi, Y.; Kuwajima, I.; Tsuruo, T.; Synthesis of C-ring aromatic taxoids and evaluation of their multi-drug resistance reversing activity. Bioorg Med Chem Lett 1998, 8, 21, 2973.

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)	27204	(1S)-1-hydroxy-4,6,6-trimethyl-5-[(E)-(phenylsulfanyl)methylidene]-3-[(triisopropylsilyl)oxy]-3-cyclohexene-1-carbaldehyde		C₂₆H₄₀O₃SSi	详情	详情
(II)	27205	[2-(1,3-dioxolan-2-yl)-6-(methoxymethoxy)phenyl]lithium		C₁₁H₁₃LiO₄	详情	详情
(III)	27206	(1S)-1-[[2-(1,3-dioxolan-2-yl)-6-(methoxymethoxy)phenyl](hydroxy)methyl]-4,6,6-trimethyl-5-[(E)-(phenylsulfanyl)methylidene]-3-[(triisopropylsilyl)oxy]-3-cyclohexen-1-ol		C₃₇H₅₄O₇SSi	详情	详情
(IV)	27207	(5S)-4-[2-(1,3-dioxolan-2-yl)-6-(methoxymethoxy)phenyl]-2,8,10,10-tetramethyl-9-[(E)-(phenylsulfanyl)methylidene]-1,3-dioxa-2-boraspiro[4.5]dec-7-en-7-yl triisopropylsilyl ether		C₃₈H₅₅BO₇SSi	详情	详情
(V)	27208	(1S,2S,9R,10R)-1,2,4-trihydroxy-9-(2-hydroxyethoxy)-12,15,15-trimethyl-10-(phenylsulfanyl)tricyclo[9.3.1.0(3,8)]pentadeca-3,5,7,11-tetraen-13-one		C₂₆H₃₀O₆S	详情	详情
(VI)	27209	2-nitroacetamide		C₂H₄N₂O₃	详情	详情
(VII)	10202	Benzoic acid	65-85-0	C₇H₆O₂	详情	详情

Extended Information