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【结 构 式】

【分子编号】45943

【品名】(2R,3R,4R,5R)-1,2,3,4,5-heptanepentol

【CA登记号】

【 分 子 式 】C7H16O5

【 分 子 量 】180.20104

【元素组成】C 46.66% H 8.95% O 44.39%

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:(I)

The reaction of D-mannitol (I) with acetone and ZnCl2 gives the diacetonide (II), which is oxidized with Pb(OAc)4 to yield the acetonide of (R)-glyceraldehyde (III). The reduction of (III) with H2 over Pd/C affords the (S)-glycerin acetonide (IV), which is treated with TsCl in pyridine to provide the corresponding tosylate (V). The condensation of (V) with the urea derivative (VI) by means of KOH in DMSO gives the adduct (VII), which is deprotected with HCl in acetone to yield the diol (VIII). Monotosylation of (VIII) with TsCl in pyridine affords the primary tosylate (IX), which is treated with Na in methanol to provide the epoxide (X). Finally this compound is treated with tert-butylamine to furnish the target (R)-enantiomer.

1 Hofer, O.; Schlogl, K.; Absolute configuration and enantiomeric purity of celiprolol. Arzneim-Forsch Drug Res 1986, 36, 8, 1157.
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) 45943 (2R,3R,4R,5R)-1,2,3,4,5-heptanepentol C7H16O5 详情 详情
(II) 45944 (1S,2S)-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2-ethanediol 1707-77-3 C12H22O6 详情 详情
(III) 36759 (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 15186-48-8 C6H10O3 详情 详情
(IV) 12698 [(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]methanol 14347-78-5 C6H12O3 详情 详情
(V) 15208 (S)-(+)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxolane-p-toluenesulfonate; [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate 23735-43-5 C13H18O5S 详情 详情
(VI) 33817 N'-(3-acetyl-4-hydroxyphenyl)-N,N-diethylurea C13H18N2O3 详情 详情
(VII) 45945 N'-(3-acetyl-4-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]phenyl)-N,N-diethylurea C19H28N2O5 详情 详情
(VIII) 45946 N'-(3-acetyl-4-[[(2R)-2,3-dihydroxypropyl]oxy]phenyl)-N,N-diethylurea C16H24N2O5 详情 详情
(IX) 45947 (2S)-3-(2-acetyl-4-[[(diethylamino)carbonyl]amino]phenoxy)-2-hydroxypropyl 4-methylbenzenesulfonate C23H30N2O7S 详情 详情
(X) 45948 N'-[3-acetyl-4-[(2R)oxiranylmethoxy]phenyl]-N,N-diethylurea C16H22N2O4 详情 详情
(XI) 17895 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine 75-64-9 C4H11N 详情 详情
Extended Information