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【结 构 式】

【分子编号】19237

【品名】(2R)-1-(benzyloxy)-2-propanol

【CA登记号】

【 分 子 式 】C10H14O2

【 分 子 量 】166.21996

【元素组成】C 72.26% H 8.49% O 19.25%

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:(XII)

2) The reaction of the previously described (R)-2-(2-tetrahydropyranyloxy)-1-propanol (III) with benzyl bromide (XI) by means of NaH in DMF, followed by a treatment with Dowex 50X, gives 1-benzyloxy-2(R)-propanol (XII), which is condensed with tosyloxymethylphosphonic acid diisopropyl ester (IX) by means of NaH in THF, yielding 2-benzyloxy-1(R)-methylethoxymethylphosphonic acid diisopropyl ester (XIII). The hydrogenolysis of (XIII) over Pd/C in methanol affords 2-hydroxy-1(R)-methylethoxymethylphosphonic acid diisopropyl ester (XIV), which is tosylated with tosyl chloride/dimethyl-aminopyridine in pyridine to give the expected tosylate (XV). The condensation of (XV) with adenine (VI) by means of Cs2CO3 in hot DMF yields 9-[2(R)-(diisopropoxyphosphorylmethoxy)propyl]adenine (X), which is finally hydrolyzed as before.

1 Masojídková, M.; Holý, A.; Synthesis of enantiomeric N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases. I. The stepwise approach. Coll Czech Chem Commun 1995, 60, 7, 1196.
2 Sorbera, L.A.; Castañer, J.; (R)-PMPA and Bis(POC)PMPA. Drugs Fut 1998, 23, 12, 1279.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 19228 (2S)-2-(tetrahydro-2H-pyran-2-yloxy)-1-propanol 76946-21-9 C8H16O3 详情 详情
(V) 10343 9H-Purin-6-amine; 9H-Purin-6-ylamine; Adenine 73-24-5 C5H5N5 详情 详情
(IX) 19234 (diisopropoxyphosphoryl)methyl 4-methylbenzenesulfonate C14H23O6PS 详情 详情
(X) 19235 diisopropyl [[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethyl]oxy]methylphosphonate C15H26N5O4P 详情 详情
(XI) 12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
(XII) 19237 (2R)-1-(benzyloxy)-2-propanol C10H14O2 详情 详情
(XIII) 19238 diisopropyl [[(1S)-2-(benzyloxy)-1-methylethyl]oxy]methylphosphonate C17H29O5P 详情 详情
(XIV) 19239 diisopropyl [[(1S)-2-hydroxy-1-methylethyl]oxy]methylphosphonate C10H23O5P 详情 详情
(XV) 19240 (2S)-2-[(diisopropoxyphosphoryl)methoxy]propyl 4-methylbenzenesulfonate C17H29O7PS 详情 详情
Extended Information