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【结 构 式】

【分子编号】46215

【品名】(2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-(tritylsulfanyl)propionic acid

【CA登记号】

【 分 子 式 】C37H31NO4S

【 分 子 量 】585.72348

【元素组成】C 75.87% H 5.33% N 2.39% O 10.93% S 5.47%

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:(XI)

The same synthesis can be performed but following an Fmoc/tBu strategy: Derivative (IV) is coupled to cysteines (XI) and (VI) by means of HBTU to yield compound (XII), which is then subjected to simultaneous Trt removal and oxidation by means of iodine in CHCl3/MeOH to provide cystine derivative (XIII). Basic deprotection of (XIII) followed by coupling to protected tyrosine (XIV) and final deprotection of the resulting compound furnishes the desired compound. Alternatively, (XII) can be first subjected to basic deprotection to allow next coupling with protected tyrosine (XIV), furnishing derivative (XV), which is finally oxidized with iodine in CHCl3/MeOH and further deprotected to yield the desired cyclic cystine compound.

1 Cook, C.; Kaplan, G.; Fry, D.; Tilley, J.W.; Wolitzky, B.; Hanglow, A.; Joshi, P.; Rowan, K.; Schwinge, V.; Fotouhi, N.; The design and synthesis of potent cyclic peptide VCAM-VLA-4 antagonists incorporating an achiral Asp-Pro mimetic. Bioorg Med Chem Lett 2000, 10, 11, 1171.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 46210 1-(2-azidoethyl)cyclopentanecarboxylic acid C8H13N3O2 详情 详情
(XI) 46215 (2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-(tritylsulfanyl)propionic acid C37H31NO4S 详情 详情
(XII) 46211 tert-butyl (2R)-2-amino-3-(tritylsulfanyl)propanoate C26H29NO2S 详情 详情
(XIII) 46216 tert-butyl (2R)-2-([[1-(2-[[(2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-(tritylsulfanyl)propanoyl]amino]ethyl)cyclopentyl]carbonyl]amino)-3-(tritylsulfanyl)propanoate C71H71N3O6S2 详情 详情
(XIV) 46217 tert-butyl (8R,13R)-13-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-6,14-dioxo-10,11-dithia-7,15-diazaspiro[4.12]heptadecane-8-carboxylate C33H41N3O6S2 详情 详情
(XV) 46218 (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-(4-hydroxyphenyl)propionic acid C24H21NO5 详情 详情
Extended Information