　 -Drug Synthesis Database

【结构式】

【分子编号】41790

【品名】　

【CA登记号】

【分子式】C₃₄H₃₅Cl₃N₄O₁₀S

【分子量】798.09696

【元素组成】C 51.17% H 4.42% Cl 13.33% N 7.02% O 20.05% S 4.02%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XVII)

Reaction of (IX) with MOM-Br and DIEA as before affords the ether (X), which is treated with Zn/HOAc in order to regenerate the primary amino group giving (XI). The reaction of (XI) with NaNO2 and HOAc eliminates the NH2 group, affording the primary alcohol (XII), which is esterified with the protected (S)-cysteine (XIII) by means of EDC and DMAP in dichloromethane furnishing the cysteine ester (XIV). Reaction of (XIV) with Bu3SnH and PdCl2(PPh3)2, followed by oxidation with (PhSeO)2O in dichloromethane gives the hydroxyketone (XV), which is cyclized with Tf2O and Ac2O yielding the heptacyclic compound (XVI). Elimination of the MOM protecting group with TMSCl and NaI in CH3CN/CH2Cl2 affords the phenolic compound (XVII).

参考文献中间体

合成目标

【1】 Cuevas, C.; Martin, M.J.; Perez, M.; et al.; Synthesis of ecteinascidin ET-743 and phathalascidin Pt-650 from cyanosafracin B. Org Lett 2000, 2, 16, 2545.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IX)	41782	2,2,2-trichloroethyl [(1S,2S,13R,15R,16R)-5-(allyloxy)-15-cyano-22-hydroxy-21-methoxy-6,20,24-trimethyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,18,20,22-hexaen-13-yl]methylcarbamate	C₃₂H₃₅Cl₃N₄O₇	详情	详情
(X)	41783	2,2,2-trichloroethyl [(1S,2S,13R,15R,16R)-5-(allyloxy)-15-cyano-21-methoxy-22-(methoxymethoxy)-6,20,24-trimethyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,18,20,22-hexaen-13-yl]methylcarbamate	C₃₄H₃₉Cl₃N₄O₈	详情	详情
(XI)	41784	(1S,2S,13R,15R,16R)-5-(allyloxy)-13-(aminomethyl)-21-methoxy-22-(methoxymethoxy)-6,20,24-trimethyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,18,20,22-hexaene-15-carbonitrile	C₃₁H₃₈N₄O₆	详情	详情
(XII)	41785	(1S,2S,13R,15R,16R)-5-(allyloxy)-13-(hydroxymethyl)-21-methoxy-22-(methoxymethoxy)-6,20,24-trimethyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,18,20,22-hexaene-15-carbonitrile	C₃₁H₃₇N₃O₇	详情	详情
(XIII)	41786	(2S)-3-[(9H-fluoren-9-ylmethyl)sulfanyl]-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]propionic acid	C₂₀H₁₈Cl₃NO₄S	详情	详情
(XIV)	41787	[(1S,2S,13R,15R,16R)-5-(allyloxy)-15-cyano-21-methoxy-22-(methoxymethoxy)-6,20,24-trimethyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,18,20,22-hexaen-13-yl]methyl (2S)-3-[(9H-fluoren-9-ylmethyl)sulfanyl	C₅₁H₅₃Cl₃N₄O₁₀S	详情	详情
(XV)	41788		C₄₈H₄₉Cl₃N₄O₁₁S	详情	详情
(XVI)	41789		C₃₆H₃₉Cl₃N₄O₁₁S	详情	详情
(XVII)	41790		C₃₄H₃₅Cl₃N₄O₁₀S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XVII)

Intermediate (XVII) by a treatment with Zn and HOAc eliminates the Troc protecting group, giving the primary amine (XVIII). This compound by treatment with 4-formyl-1-methylpyridinium iodide (NMPC), DBU and oxalic acid in order to convert the nitrile group into an alcohol, provides compund (XIX), which is finally cyclized with 2-(3-hydroxy-4-methoxyphenyl)ethylamine (XX) by means of SiO2 / EtOH, followed treatment with and AgNO3 in acetonitrile/water.

参考文献中间体

合成目标

【1】 Cuevas, C.; Martin, M.J.; Perez, M.; et al.; Synthesis of ecteinascidin ET-743 and phathalascidin Pt-650 from cyanosafracin B. Org Lett 2000, 2, 16, 2545.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XVII)	41790		C₃₄H₃₅Cl₃N₄O₁₀S	详情	详情
(XVIII)	41791	(1R,2R,3S,11R,12R,14R,26R)-26-amino-12-cyano-5-hydroxy-6-methoxy-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 acetate	C₃₁H₃₄N₄O₈S	详情	详情
(XIX)	41792	(1R,2R,3S,11R,12S,14R,26R)-26-amino-5,12-dihydroxy-6-methoxy-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 acetate	C₃₀H₃₅N₃O₉S	详情	详情
(XX)	36471	5-(2-aminoethyl)-2-methoxyphenol	C₉H₁₃NO₂	详情	详情

Extended Information