1,2-Dichloroethane → (S)-benzyl 2-{[(benzyloxy)carbonyl]amino}-5-[(2-{[alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl]oxy}ethyl)amino]-5-oxopentanoate

HRID 1488265노트

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HRID 1488265 반응식
[C@H:1]1([O:12][C@H:13]2[C@H:22]([OH:23])[C@@H:21]([CH2:24][O:25][C@H:26]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@@H:27]3[OH:28])[O:20][C@H:15]([O:16][CH2:17][CH2:18][NH2:19])[C@H:14]2[OH:37])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3].[CH2:38]([O:45][C:46](=[O:64])[C@@H:47]([NH:53][C:54]([O:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)=[O:55])[CH2:48][CH2:49][C:50](O)=[O:51])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:57]([O:56][C:54]([NH:53][C@@H:47]([CH2:48][CH2:49][C:50]([NH:19][CH2:18][CH2:17][O:16][C@H:15]1[O:20][C@H:21]([CH2:24][O:25][C@H:26]2[O:34][C@H:33]([CH2:35][OH:36])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@@H:27]2[OH:28])[C@@H:22]([OH:23])[C@H:13]([O:12][C@H:1]2[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]2[OH:3])[C@@H:14]1[OH:37])=[O:51])[C:46]([O:45][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:64])=[O:55])[C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1

참가 물질

6

반응물 3

HCID 111,2-DichloroethaneHCID 6994031(4S)-5-(Benzyloxy)-4-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acidHCID 117136792-Aminoethyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranoside

생성물 1

HCID 131736861(S)-benzyl 2-{[(benzyloxy)carbonyl]amino}-5-[(2-{[alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl]oxy}ethyl)amino]-5-oxopentanoate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-aminoethyl α-D-mannopyranosyl-(1→3)-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranoside (2.6 g, 4.75 mmol), and (S)-5-(benzyloxy)-4-{[(benzyloxy)carbonyl]amino}-5-oxopentanoic acid (2.0 g, 5.39 mmol) in DMF (36 mL) at 0° C. was added DMAP (580 mg, 4.75 mmol) and EDC (3.64 g, 19.00 mmol). The reaction mixture was allowed to gradually warm up to rt. After stirring for 16 hr, the reaction mixture was concentrated and the residue was purified by flash chromatography on C18 reverse phase silica gel (275 g), eluting with 10-55% AcCN in H2O to give the title compound. UPLC Method B: calculated for C40H56N2O21 900.34, observed m/e: 901.26 [M+1]; Rt=2.46 min.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography on C18 reverse phase silica gel (275 g)
  3. washeluting with 10-55% AcCN in H2O

출처 및 근거

ORD 기록
ord-886bd37acf324f94a594226c512abcb1
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09427475B2

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