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【结 构 式】 
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【分子编号】26404 【品名】 【CA登记号】 |
【 分 子 式 】C72H81Br2Cl2IO22S2 【 分 子 量 】1720.17181 【元素组成】C 50.27% H 4.75% Br 9.29% Cl 4.12% I 7.38% O 20.46% S 3.73% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of disulfide (I) with SOCl2 gives the corresponding acyl chloride (II), which is then condensed with L-isoleucine (III) by means of NaHCO3 in THF.
| 【1】 Fiore, P.J.; et al.; Development and pilot-scale demonstration of a process for inhibitors of the HIV nucleocapsid protein, NCp7. Org Process Res Dev 1998, 2, 3, 151. |
合成路线2
该中间体在本合成路线中的序号：(I)The reaction of disulfide (I) with SOCl2 gives the corresponding acyl chloride (II), which is condensed with L-isoleucine (III) by means of NaHCO3 in THF yielding the disulfide intermediate (IV). Finally, this compound is submitted to an oxidative cyclization with Br2 in acetic acid.
| 【1】 Fiore, P.J.; et al.; Development and pilot-scale demonstration of a process for inhibitors of the HIV nucleocapsid protein, NCp7. Org Process Res Dev 1998, 2, 3, 151. |
| 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) | 26404 | C72H81Br2Cl2IO22S2 | 详情 | 详情 | ||
| (II) | 20405 | 2-[[2-(chlorocarbonyl)phenyl]disulfanyl]benzoyl chloride | C14H8Cl2O2S2 | 详情 | 详情 | |
| (III) | 32739 | L-2-Amino-3-methylpentanoic acid; L-isoleucine | 73-32-5 | C6H13NO2 | 详情 | 详情 |
| (IV) | 32740 | (2S,3S)-2-[(2-[[2-([[(1S,2S)-1-carboxy-2-methylbutyl]amino]carbonyl)phenyl]disulfanyl]benzoyl)amino]-3-methylpentanoic acid | C26H32N2O6S2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(VI)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 |