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【结 构 式】 
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【分子编号】36470 【品名】(1R,2R,3R,11S,12R,14R)-12-cyano-6-methoxy-5-(methoxymethoxy)-7,21,30-trimethyl-26,27-dioxo-17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.1(3,11).0(2,13).0(4,9).0(15,23).0(16,20)]triaconta-4,6,8,15,20,22-hexaen-22-yl acetate 【CA登记号】 |
【 分 子 式 】C33H35N3O10S 【 分 子 量 】665.72112 【元素组成】C 59.54% H 5.3% N 6.31% O 24.03% S 4.82% |
合成路线1
该中间体在本合成路线中的序号：(XXII)The esterification of the primary OH group of (XVIII) with the protected cysteine (XIX) by means of EDC and DMAP in dichloromethane gives ester (XX), which is cyclized by means of trifluoromethanesulfonic anhydride and DMSO yielding the bridged lactone (XXI). The oxidation of (XXI) with N-methylpyridinium-4-carbaldehyde (NMPA), DBU and PdCl2(PPh3)2 affords the oxolactone (XXII), which is finally cyclized with 2-(3-hydroxy-4-methoxyphenyl)ethylamine (XXIII) by means of TFA and AgNO3 in water.
| 【1】 Gin, D.Y.; Corey, E.J.; Kania, R.S.; Enantioselective total synthesis of Ecteinascidin 743. J Am Chem Soc 1996, 118, 38, 9202-03. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
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| (XVIII) | 36466 | (1R,2S,4R,13R,15R,16S)-4-hydroxy-13-(hydroxymethyl)-21-methoxy-22-(methoxymethoxy)-6,20,24-trimethyl-5-oxo-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-6,11,18,20,22-pentaene-15-carbonitrile | C28H33N3O8 | 详情 | 详情 | |
| (XIX) | 36467 | (2R)-2-[[(allyloxy)carbonyl]amino]-3-[(9H-fluoren-9-ylmethyl)sulfanyl]propionic acid | C21H21NO4S | 详情 | 详情 | |
| (XX) | 36468 | C49H52N4O11S | 详情 | 详情 | ||
| (XXI) | 36469 | (1R,2R,3R,11S,12R,14R)-26-[[(allyloxy)carbonyl]amino]-12-cyano-6-methoxy-5-(methoxymethoxy)-7,21,30-trimethyl-27-oxo-17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.1(3,11).0(2,13).0(4,9).0(15,23).0(16,20)]triaconta-4,6,8,15,20,22-hexaen-22-yl | C37H42N4O11S | 详情 | 详情 | |
| (XXII) | 36470 | (1R,2R,3R,11S,12R,14R)-12-cyano-6-methoxy-5-(methoxymethoxy)-7,21,30-trimethyl-26,27-dioxo-17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.1(3,11).0(2,13).0(4,9).0(15,23).0(16,20)]triaconta-4,6,8,15,20,22-hexaen-22-yl acetate | C33H35N3O10S | 详情 | 详情 | |
| (XXIII) | 36471 | 5-(2-aminoethyl)-2-methoxyphenol | C9H13NO2 | 详情 | 详情 |