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HRID1488265

反应详情

EQUATION

反应方程式

HRID 1488265 的结构方程式

REACTANTS

反应物

3
结构：ClCCCl
HCID11

1,2-Dichloroethane

C2H4Cl2

结构：O=C(O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1
HCID6994031

(4S)-5-(Benzyloxy)-4-{[(benzyloxy)carbonyl]amino}-5-oxopentanoic acid

C20H21NO6

结构：NCCO[C@H]1O[C@H](CO[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](O)[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H]1O
HCID11713679

未命名化合物

PRODUCTS

生成物

1
结构：O=C(CC[C@H](NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)NCCO[C@H]1O[C@H](CO[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](O)[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H]1O
HCID131736861

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CN(C)c1ccncc1
催化剂HCID14284

N,N-Dimethylpyridin-4-amine

C7H10N2

结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

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.

WORKUP

后处理

  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