tert-butyldimethylsilyl 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-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 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-glucopyranoside
CAS No.:678159-12-1
Molecular Formula:C₅₃H₆₄N₂O₁₄Si
Molecular Weight:981.182
Hs Code.:

tert-butyldimethylsilyl 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-glucopyranoside

Synonyms:tert-butyldimethylsilyl 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-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl 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-glucopyranoside

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Technology Process of tert-butyldimethylsilyl 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-glucopyranoside

There total 16 articles about tert-butyldimethylsilyl 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-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: 71.0%

: 216877-47-3
tert-butyldimethylsilyl 3,6-di-O-benzyl-2-deoxy-2-dimethylmaleoylamido-glucopyranoside

: 678159-06-3
3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl trichloroacetimidate

: 678159-12-1
tert-butyldimethylsilyl 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-glucopyranoside

Guidance literature:: With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; at -10 - 20 ℃; for 2h;
DOI:10.1021/jo035583k

Reference yield:

: 766-39-2
2,3-Dimethylmaleic anhydride

: 678159-12-1
tert-butyldimethylsilyl 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-glucopyranoside

Guidance literature:: Multi-step reaction with 10 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

With pyridine; 1H-imidazole; trifluorormethanesulfonic acid; 4 A molecular sieve; 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;
DOI:10.1021/jo035583k

Reference yield:

: 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
2-deoxy-2-amino glucose

: 678159-12-1
tert-butyldimethylsilyl 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-glucopyranoside

Guidance literature:: Multi-step reaction with 10 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

With pyridine; 1H-imidazole; trifluorormethanesulfonic acid; 4 A molecular sieve; 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;
DOI:10.1021/jo035583k