methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
• CAS No.: 678159-17-6
• Molecular Formula: C₆₉H₇₇N₃O₂₁
• Molecular Weight: 1284.38

Synonyms:methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Chemical Property of methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Chemical Property:

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Technology Process of methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

There total 26 articles about methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside (678159-16-5) → methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside (678159-17-6)

Guidance literature:

With trimethylamine-borane; boron trifluoride diethyl etherate; In acetonitrile; at 0 - 20 ℃; for 1.5h;

DOI:10.1021/jo035583k

Reference yield:

2,3-Dimethylmaleic anhydride (766-39-2) → methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside (678159-17-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 68 percent / N₂H₄*AcOH

2: 78 percent / imidazole

3: 73 percent / NaOMe

4: 91 percent / TsOH

5: 85 percent / pyridine / CH₂Cl₂ / 20 °C

6: 63 percent / TBAF; AcOH / tetrahydrofuran; ethyl acetate / 0.5 h / -10 °C

7: 1,8-diazabicyclo[5.4.0]undec-7-ene; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

8: 71 percent / TfOH / CH₂Cl₂; cyclohexane / 2 h / -10 - 20 °C

9: 75 percent / n-Bu₄NF / tetrahydrofuran; ethyl acetate / 1 h / -20 °C

10: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / cooling

11: 55 percent / TfOH; 4 Angstroem molecular sieves / CH₂Cl₂ / -5 °C

12: 62 percent / BH₃*NMe₃; BF₃*Et₂O / acetonitrile / 1.5 h / 0 - 20 °C

With pyridine; 1H-imidazole; trifluorormethanesulfonic acid; trimethylamine-borane; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; hydrazinium monoacetate; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; cyclohexane; ethyl acetate; acetonitrile;

DOI:10.1021/jo035583k

Reference yield:

2-deoxy-2-amino glucose (90-76-6,90-77-7,530-23-4,579-32-8,579-33-9,643-68-5,2596-19-2,6490-68-2,6490-70-6,6490-72-8,6490-73-9,6490-74-0,14196-84-0,14196-86-2,14257-69-3,58381-21-8) → methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside (678159-17-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 68 percent / N₂H₄*AcOH

2: 78 percent / imidazole

3: 73 percent / NaOMe

4: 91 percent / TsOH

5: 85 percent / pyridine / CH₂Cl₂ / 20 °C

6: 63 percent / TBAF; AcOH / tetrahydrofuran; ethyl acetate / 0.5 h / -10 °C

7: 1,8-diazabicyclo[5.4.0]undec-7-ene; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

8: 71 percent / TfOH / CH₂Cl₂; cyclohexane / 2 h / -10 - 20 °C

9: 75 percent / n-Bu₄NF / tetrahydrofuran; ethyl acetate / 1 h / -20 °C

10: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / cooling

11: 55 percent / TfOH; 4 Angstroem molecular sieves / CH₂Cl₂ / -5 °C

12: 62 percent / BH₃*NMe₃; BF₃*Et₂O / acetonitrile / 1.5 h / 0 - 20 °C

With pyridine; 1H-imidazole; trifluorormethanesulfonic acid; trimethylamine-borane; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; hydrazinium monoacetate; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; cyclohexane; ethyl acetate; acetonitrile;

DOI:10.1021/jo035583k

upstream raw materials:

methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

2,3-Dimethylmaleic anhydride

2-deoxy-2-amino glucose

benzaldehyde dimethyl acetal

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