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【结 构 式】

【分子编号】57539

【品名】(3R)-3-[(4-methoxybenzyl)oxy]tetradecyl methanesulfonate

【CA登记号】

【 分 子 式 】C23H40O5S

【 分 子 量 】428.6336

【元素组成】C 64.45% H 9.41% O 18.66% S 7.48%

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:(XVI)

The chiral diol (XII) is converted to the dioxane derivative (XIV) by treatment with anisaldehyde dimethyl acetal (XIII) in the presence of p-toluenesulfonic acid. Reductive cleavage of dioxane (XIV) by means of DIBAL produces regioselectively the mono-p-methoxybenzyl ether (XV). The primary alcohol group of (XV) is then converted to the corresponding mesylate (XVI) employing methanesulfonyl chloride and triethylamine. Alkylation of the protected glucosamine (XVII) with mesylate (XVI) in the presence of NaH yields ether (XVIII). After basic hydrolysis of the trifluoroacetamide (XVIII), the resultant amine (XIX) is reprotected as the trichloroethyl carbamate (XX) by using trichloroethyl chloroformate and NaHCO3. Subsequent hydrolysis of the acetonide group of (XX) provides diol (XXI).

1 Nishijima, M.; Kurakata, S.-I.; Shiozaki, M.; Mochizuki, T.; Kanai, S.; Watanabe, Y.; Synthesis of lipid A type pyran carboxylic acids with ether chains and their biological activities. Carbohydr Res 2001, 333, 3, 203.
2 Shiozaki, M.; Kurakata, S.; Kanai, S.; Kazama, Y. (Sankyo Co., Ltd.); Ether type lipid A1-carboxylic acid analogues. EP 1152007; JP 2000297096; US 2002161221; US 6511965; WO 0047595 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XII) 57536 (3R)-1,3-tetradecanediol C14H30O2 详情 详情
(XIII) 26485 1-(dimethoxymethyl)-4-methoxybenzene 2186-92-7 C10H14O3 详情 详情
(XIV) 57537 (4R)-2-(4-methoxyphenyl)-4-undecyl-1,3-dioxane; methyl 4-[(4R)-4-undecyl-1,3-dioxan-2-yl]phenyl ether C22H36O3 详情 详情
(XV) 57538 (3R)-3-[(4-methoxybenzyl)oxy]-1-tetradecanol C22H38O3 详情 详情
(XVI) 57539 (3R)-3-[(4-methoxybenzyl)oxy]tetradecyl methanesulfonate C23H40O5S 详情 详情
(XVII) 57540 N-[(4aR,6S,7R,8R,8aS)-6-(allyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2,2,2-trifluoroacetamide C14H20F3NO6 详情 详情
(XVIII) 57541 N-((4aR,6S,7R,8R,8aS)-6-(allyloxy)-8-{[(3R)-3-(2-[1,1'-biphenyl]-4-ylethoxy)tetradecyl]oxy}-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)-2,2,2-trifluoroacetamide C42H60F3NO7 详情 详情
(XIX) 57542 (4aR,6S,7R,8R,8aS)-6-(allyloxy)-8-{[(3R)-3-(2-[1,1'-biphenyl]-4-ylethoxy)tetradecyl]oxy}-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-amine; (4aR,6S,7R,8R,8aS)-6-(allyloxy)-8-{[(3R)-3-(2-[1,1'-biphenyl]-4-ylethoxy)tetradecyl]oxy}-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-ylamine C40H61NO6 详情 详情
(XX) 57543 2,2,2-trichloroethyl (4aR,6S,7R,8R,8aS)-6-(allyloxy)-8-{[(3R)-3-(2-[1,1'-biphenyl]-4-ylethoxy)tetradecyl]oxy}-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-ylcarbamate C43H62Cl3NO8 详情 详情
(XXI) 57544 2,2,2-trichloroethyl (2S,3R,4R,5S,6R)-2-(allyloxy)-4-{[(3R)-3-(2-[1,1'-biphenyl]-4-ylethoxy)tetradecyl]oxy}-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-ylcarbamate C40H58Cl3NO8 详情 详情
Extended Information