(1S,2S,3R,4S,5S)-1-(hydroxymethyl)-5-(methylamino)-1,2,3,4-cyclohexanetetrol -Drug Synthesis Database

【结构式】

【分子编号】24265

【品名】(1S,2S,3R,4S,5S)-1-(hydroxymethyl)-5-(methylamino)-1,2,3,4-cyclohexanetetrol

【CA登记号】

【分子式】C₈H₁₇NO₅

【分子量】207.22672

【元素组成】C 46.37% H 8.27% N 6.76% O 38.6%

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：(VI)

The acylation of valienamine (I) with benzyloxycarbonyl chloride (II) by means of NaHCO3 in ethyl acetate gives the corresponding N-benzyloxycarbonyl derivative (III), which by reaction with Br2 in water is converted to the cyclic carbamate (IV). Elimination of bromine from (IV) with NaBH4 in water affords the new cyclic carbamate (V), which by hydrolysis with Ba(OH)2 in refluxing water is converted to valiolamine (VI). Finally, this compound is reductocondensed with 1,3-dihydroxyacetone (VII) and sodium cyanoborohydride in DMF 2N HCl.

参考文献中间体

合成目标

【1】 Horii, S.; et al.; Synthesis and alpha-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents. J Med Chem 1986, 29, 6, 1038.
【2】 Horii, S.; Kameda, Y.; Fukase, H. (Takeda Chemical Industries, Ltd.); N-substituted pseudo-aminosugars, their production and use. EP 0056194; US 4701559; US 4777294; US 4803303 .
【3】 Prous, J.; Castaner, J.; AO-128. Drugs Fut 1986, 11, 9, 729.

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)	24260	(1S,2S,3R,6S)-4-(hydroxymethyl)-6-(methylamino)-4-cyclohexene-1,2,3-triol		C₈H₁₅NO₄	详情	详情
(II)	24261	1-[2-(chlorooxy)-2-oxoethyl]benzene		C₈H₇ClO₂	详情	详情
(III)	24262	(1S,2S,3R,6S)-4-(hydroxymethyl)-6-[methyl[(2-phenylacetyl)oxy]amino]-4-cyclohexene-1,2,3-triol		C₁₆H₂₁NO₆	详情	详情
(IV)	24263	(1S,5R,6S,7R,8S,9S)-9-bromo-6,7,8-trihydroxy-1-(hydroxymethyl)-4-methyl-2-oxa-4-azabicyclo[3.3.1]nonan-3-one		C₉H₁₄BrNO₆	详情	详情
(V)	24264	(1S,5S,6S,7R,8S)-6,7,8-trihydroxy-1-(hydroxymethyl)-4-methyl-2-oxa-4-azabicyclo[3.3.1]nonan-3-one		C₉H₁₅NO₆	详情	详情
(VI)	24265	(1S,2S,3R,4S,5S)-1-(hydroxymethyl)-5-(methylamino)-1,2,3,4-cyclohexanetetrol		C₈H₁₇NO₅	详情	详情
(VII)	14575	Dihydroxyacetone; 1,3-dihydroxyacetone	96-26-4	C₃H₆O₃	详情	详情

Extended Information