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【结 构 式】

【分子编号】48937

【品名】(2S,3R,4S,5S)-3,5-bis(acetoxy)-2-(phenylsulfanyl)tetrahydro-2H-pyran-4-yl acetate

【CA登记号】

【 分 子 式 】C17H20O7S

【 分 子 量 】368.4076

【元素组成】C 55.42% H 5.47% O 30.4% S 8.7%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(II)

Synthesis of intermediate monosaccharide (VIII): The reaction of the tetraacetyl-L-arabinose (I) with Ph-SH and SnCl4 gives the thioglycoside (II), which is deacetylated with NaOMe in methanol, yielding compound (III). The reaction of (III) with 2,2-dimethoxypropane (IV) and CSA in dichloromethane affords the acetonide (V), which is acetylated with Ac2O, DMAP and TEA to provide the acetate (VI). Elimination of the acetonide group of (VI) with Amberlite IR-118B furnishes diol (VII), which is selectively silylated with Tes-OTf and lutidine in dichloromethane to afford the desired intermediate monosaccharide (VIII).

1 Jin, Z.; Yu, W.; A new strategy for the stereoselective introduction of steroid side chain via alpha-alkoxy vinyl cuprates: Total synthesis of a highly potent antitumor natural product OSW-1. J Am Chem Soc 2001, 123, 14, 3369.
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) 48936 D-Arabinose tetraacetate C13H18O9 详情 详情
(II) 48937 (2S,3R,4S,5S)-3,5-bis(acetoxy)-2-(phenylsulfanyl)tetrahydro-2H-pyran-4-yl acetate C17H20O7S 详情 详情
(III) 48938 (2S,3R,4S,5S)-2-(phenylsulfanyl)tetrahydro-2H-pyran-3,4,5-triol C11H14O4S 详情 详情
(IV) 10722 1-Methoxy-1-methylethyl methyl ether; 2,2-Dimethoxypropane 77-76-9 C5H12O2 详情 详情
(V) 48939 (3aS,6S,7R,7aR)-2,2-dimethyl-6-(phenylsulfanyl)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol C14H18O4S 详情 详情
(VI) 48940 (3aS,6S,7R,7aS)-2,2-dimethyl-6-(phenylsulfanyl)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-yl acetate C16H20O5S 详情 详情
(VII) 48941 (2S,3R,4S,5S)-4,5-dihydroxy-2-(phenylsulfanyl)tetrahydro-2H-pyran-3-yl acetate C13H16O5S 详情 详情
(VIII) 48942 (2S,3R,4R,5S)-4-hydroxy-2-(phenylsulfanyl)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl acetate C19H30O5SSi 详情 详情

合成路线2

该中间体在本合成路线中的序号:(II)

. L- Arabinose monosaccharide intermediate (VIII): The reaction of tetraacetyl-L-arabinose (I) with Ph-SH by means of SnCl4 in dichloromethane gives the acetylated thioglycoside (II), which is deacetylated by means of NaOMe in methanol to yield thioglycoside (III). The reaction of (III) with 2,2-dimethoxypropane (IV) and CSA in dichloromethane affords the acetonide (V), which is acetylated with Ac2O, TEA and DMAP to provide monoacetate (VI). The cleavage of the acetonide group of (VI) by means of Amberlite IR-118H leads to the monoacetylated thioglycoside (VII), which is finally selectively monosilylated with Tms-OTf and lutidine in dichloromethane the target L-arabinose intermediate (VIII)

1 Yu, W.; Jin, Z.; Total synthesis of the anticancer natural product OSW-1. J Am Chem Soc 2002, 124, 23, 6576.
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) 48936 D-Arabinose tetraacetate C13H18O9 详情 详情
(II) 48937 (2S,3R,4S,5S)-3,5-bis(acetoxy)-2-(phenylsulfanyl)tetrahydro-2H-pyran-4-yl acetate C17H20O7S 详情 详情
(III) 48938 (2S,3R,4S,5S)-2-(phenylsulfanyl)tetrahydro-2H-pyran-3,4,5-triol C11H14O4S 详情 详情
(IV) 10722 1-Methoxy-1-methylethyl methyl ether; 2,2-Dimethoxypropane 77-76-9 C5H12O2 详情 详情
(V) 48939 (3aS,6S,7R,7aR)-2,2-dimethyl-6-(phenylsulfanyl)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol C14H18O4S 详情 详情
(VI) 48940 (3aS,6S,7R,7aS)-2,2-dimethyl-6-(phenylsulfanyl)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-yl acetate C16H20O5S 详情 详情
(VII) 48941 (2S,3R,4S,5S)-4,5-dihydroxy-2-(phenylsulfanyl)tetrahydro-2H-pyran-3-yl acetate C13H16O5S 详情 详情
(VIII) 48942 (2S,3R,4R,5S)-4-hydroxy-2-(phenylsulfanyl)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl acetate C19H30O5SSi 详情 详情
Extended Information