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【结 构 式】 
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【分子编号】26401 【品名】8-(Benzyloxymethoxy)-2-[6-bromo-4-O-(2-chloroacetyl)-2,6-dideoxy-2-(phenylsulfanyl)-3-O-(triethylsilyl)-beta-D-glucopyranosyloxy]-6,9-bis(2(E)-butenyloxy)-3(S)-[1(S)-methoxy-2-[5(R)-methylspiro[1,3-dioxolane-2,1'-cyclopent]-4(S)-yl]-2-oxoethyl]-1,2,3,4-tetrahydroanthracen-1-one; 8-(Benzyloxymethoxy)-2-[6-bromo-4-O-(2-chloroacetyl)-2,6-dideoxy-2-(phenylsulfanyl)-3-O-(triethylsilyl)-beta-D-glucopyranosyloxy]-6,9-bis(2(E)-butenyloxy)-3(S)-[1(S)-methoxy-2-[5(R)-methylspiro[1,3-dioxolane-2,1'-cyclopent]-4(S)-yl]-2-oxoethyl]-1,2,3,4-tetrahydroanthracen-1-one 【CA登记号】 |
【 分 子 式 】C61H76BrClO14SSi 【 分 子 量 】1208.77424 【元素组成】C 60.61% H 6.34% Br 6.61% Cl 2.93% O 18.53% S 2.65% Si 2.32% |
合成路线1
该中间体在本合成路线中的序号：(III)The condensation of the protected aglucone (I) with the glucoside (II) by means of TBS triflate gives the condensed alpha-glucoside (III), which is worked up to yield the bis-chloroacetylated intermediate that is desilylated to compound (IV). The condensation of (IV) with disaccharide (V) gives the trisaccharide (VI), which by deprotection of the phenolic chloroacetate and condensation with disaccharide (VII) affords the pentasaccharide (VIII).
| 【1】 Roush, W.R.; et al.; Total synthesis of olivomycin A. J Am Chem Soc 1999, 121, 9, 1990. |
| 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) | 26399 | (3R)-8-[(benzyloxy)methoxy]-6,9-bis[(E)-2-butenyloxy]-2-hydroxy-3-[(1S)-1-methoxy-2-[(2R,3R)-3-methyl-1,4-dioxaspiro[4.4]non-2-yl]-2-oxoethyl]-3,4-dihydro-1(2H)-anthracenone | C41H48O10 | 详情 | 详情 | |
| (II) | 26400 | (2S,3R,4S,5R,6R)-2-(bromomethyl)-5-(phenylsulfanyl)-6-[(2,2,2-trichloroethanimidoyl)oxy]-4-[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 2-chloroacetate | C22H30BrCl4NO5SSi | 详情 | 详情 | |
| (III) | 26401 | 8-(Benzyloxymethoxy)-2-[6-bromo-4-O-(2-chloroacetyl)-2,6-dideoxy-2-(phenylsulfanyl)-3-O-(triethylsilyl)-beta-D-glucopyranosyloxy]-6,9-bis(2(E)-butenyloxy)-3(S)-[1(S)-methoxy-2-[5(R)-methylspiro[1,3-dioxolane-2,1'-cyclopent]-4(S)-yl]-2-oxoethyl]-1,2,3,4-tetrahydroanthracen-1-one; 8-(Benzyloxymethoxy)-2-[6-bromo-4-O-(2-chloroacetyl)-2,6-dideoxy-2-(phenylsulfanyl)-3-O-(triethylsilyl)-beta-D-glucopyranosyloxy]-6,9-bis(2(E)-butenyloxy)-3(S)-[1(S)-methoxy-2-[5(R)-methylspiro[1,3-dioxolane-2,1'-cyclopent]-4(S)-yl]-2-oxoethyl]-1,2,3,4-tetrahydroanthracen-1-one | C61H76BrClO14SSi | 详情 | 详情 | |
| (IV) | 26402 | 8-(Benzyloxymethoxy)-2-[6-bromo-4-O-(2-chloroacetyl)-2,6-dideoxy-2-(phenylsulfanyl)-3-O-(triethylsilyl)-beta-D-glucopyranosyloxy]-6-(2-chloroacetoxy)-9-hydroxy-3(S)-[1(S)-methoxy-2-[5(R)-methylspiro[1,3-dioxolane-2,1'-cyclopent]-4(S)-yl]-2-oxoethyl]-1,2,3,4-tetrahydroanthracen-1-one; 8-(Benzyloxymethoxy)-2-[6-bromo-4-O-(2-chloroacetyl)-2,6-dideoxy-2-(phenylsulfanyl)-3-O-(triethylsilyl)-beta-D-glucopyranosyloxy]-6-(2-chloroacetoxy)-9-hydroxy-3(S)-[1(S)-methoxy-2-[5(R)-methylspiro[1,3-dioxolane-2,1'-cyclopent]-4(S)-yl]-2-oxoethyl]-1,2,3,4-tetrahydroanthracen-1-one | C49H51BrCl2O15S | 详情 | 详情 | |
| (V) | 26403 | (2S,3S,4R,5R,6S)-6-([(2S,3S,4S,5R,6R)-2-(bromomethyl)-3-[(2-chloroacetyl)oxy]-5-(phenylsulfanyl)-6-[(2,2,2-trichloroethanimidoyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4-hydroxy-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-yl 2-methylpropanoate | C27H33BrCl4INO9S | 详情 | 详情 | |
| (VI) | 26404 | C72H81Br2Cl2IO22S2 | 详情 | 详情 | ||
| (VII) | 26405 | (2R,3S,4S,5R,6S)-6-hydroxy-4-[[(2R,3S,4S,5R,6R)-4-hydroxy-3-iodo-5-methoxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-2-methyl-5-(phenylselanyl)tetrahydro-2H-pyran-3-yl acetate | C21H29IO8Se | 详情 | 详情 | |
| (VIII) | 26406 | C93H108Br2Cl2I2O29S2Se | 详情 | 详情 |