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【结 构 式】

【分子编号】44153

【品名】methyl 3,4,5-tris(acetoxy)-6-[4-(hydroxymethyl)phenoxy]tetrahydro-2H-pyran-2-carboxylate

【CA登记号】

【 分 子 式 】C20H24O11

【 分 子 量 】440.40396

【元素组成】C 54.55% H 5.49% O 39.96%

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:(XIII)

Intermediate (VIII) can be obtained as follows: Bromination of glucuronate derivative (X) by means of TiBr4 in CH2Cl2 followed by reaction with p-hydroxybenzaldehyde (XI) in acetonitrile in the presence of Ag2O affords derivative (XII), whose aldehyde moiety is then reduced by means of NaBH4 and silica gel in isopropanol/CHCl3 to provide benzyl alcohol (XIII). Finally, O-acetyl groups of (XIII) are cleaved by means of NaOMe in MeOH to furnish intermediate (VIII).

1 Leu, Y.-L.; Roffler, S.R.; Chern, J.-W.; Design and synthesis of water-soluble glucuronide derivatives of camptothecin for cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy (ADEPT). J Med Chem 1999, 42, 18, 3623.
2 Chern, J.-W.; Roffler, S.; Leu, Y.-L. (Academia Sinica); Proactive antitumor cpds.. EP 0990661; US 6043367 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 44150 methyl 3,4,5-trihydroxy-6-[4-(hydroxymethyl)phenoxy]tetrahydro-2H-pyran-2-carboxylate C14H18O8 详情 详情
(X) 13433 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde 123-08-0 C7H6O2 详情 详情
(XI) 44154 methyl 3,4,5,6-tetrakis(acetoxy)tetrahydro-2H-pyran-2-carboxylate C15H20O11 详情 详情
(XII) 44152 methyl 3,4,5-tris(acetoxy)-6-(4-formylphenoxy)tetrahydro-2H-pyran-2-carboxylate C20H22O11 详情 详情
(XIII) 44153 methyl 3,4,5-tris(acetoxy)-6-[4-(hydroxymethyl)phenoxy]tetrahydro-2H-pyran-2-carboxylate C20H24O11 详情 详情
Extended Information