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

Base Information

• Chemical Name: methyl 3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 871115-99-0
• Molecular Formula: C₄₄H₅₁NO₁₆
• Molecular Weight: 849.886
• Mol file: 871115-99-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about methyl 3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-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: 100.0%

O-(3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-D-glucopyranosyl) trichloroacetimidate (871115-97-8) + methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → methyl 3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (871115-99-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/ejoc.200500107

Reference yield:

1,3,4,6-tetra-O-benzyl-2-deoxy-2-diglycolylimido-β-D-glucopyranoside (871116-05-1) → methyl 3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (871115-99-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / H₂ / Pd/C / 24 h

2: 98 percent / pyridine

3: 77 percent / hydrazine acetate / dimethylformamide / 1.5 h / 20 °C

4: 80 percent / DBU / CH₂Cl₂ / 20 °C

5: 100 percent / TMSOTf / CH₂Cl₂ / 2 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; hydrogen; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200500107

Reference yield:

[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-((2R,3R,4R,5S,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl)-amine → methyl 3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (871115-99-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 82 percent / HCl / acetone / 0.33 h / Heating

2: 100 percent / pyridine; Et₃N; Ac₂O / 6.5 h / 20 - 80 °C

3: 100 percent / H₂ / Pd/C / 24 h

4: 98 percent / pyridine

5: 77 percent / hydrazine acetate / dimethylformamide / 1.5 h / 20 °C

6: 80 percent / DBU / CH₂Cl₂ / 20 °C

7: 100 percent / TMSOTf / CH₂Cl₂ / 2 h / 20 °C

With pyridine; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; hydrogen; hydrazinium monoacetate; acetic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/ejoc.200500107

upstream raw materials:

O-(3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-D-glucopyranosyl) trichloroacetimidate

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranoside

1,3,4,6-tetra-O-benzyl-2-deoxy-2-diglycolylimido-β-D-glucopyranoside

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-O-(3’,4’,6’-tri-O-acetyl-2’-N-acetyl-2’-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside