allyl 3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranosyl-(1->2)-2,3,6-tri-O-benzyl-α-D-mannopyranoside

Base Information

• Chemical Name: allyl 3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranosyl-(1->2)-2,3,6-tri-O-benzyl-α-D-mannopyranoside
• CAS No.: 871116-00-6
• Molecular Formula: C₄₆H₅₃NO₁₆
• Molecular Weight: 875.924
• Mol file: 871116-00-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about allyl 3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranosyl-(1->2)-2,3,6-tri-O-benzyl-α-D-mannopyranoside 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: 94.0%

O-(3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-D-glucopyranosyl) trichloroacetimidate (871115-97-8) + (2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol (97576-68-6) → allyl 3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranosyl-(1->2)-2,3,6-tri-O-benzyl-α-D-mannopyranoside (871116-00-6)

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) → allyl 3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranosyl-(1->2)-2,3,6-tri-O-benzyl-α-D-mannopyranoside (871116-00-6)

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: 94 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 → allyl 3,4,6-tri-O-acetyl-2-deoxy-2-diglycolylimido-β-D-glucopyranosyl-(1->2)-2,3,6-tri-O-benzyl-α-D-mannopyranoside (871116-00-6)

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: 94 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

(2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

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:

Allyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosid