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【结 构 式】

【分子编号】36467

【品名】(2R)-2-[[(allyloxy)carbonyl]amino]-3-[(9H-fluoren-9-ylmethyl)sulfanyl]propionic acid

【CA登记号】

【 分 子 式 】C21H21NO4S

【 分 子 量 】383.46808

【元素组成】C 65.78% H 5.52% N 3.65% O 16.69% S 8.36%

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:(XIX)

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
(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
Extended Information