methyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS No.: 849101-44-6
• Molecular Formula: C₅₀H₆₆N₆O₂₀
• Molecular Weight: 1071.1

Synonyms:methyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property of methyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of methyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 7 articles about methyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-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: 40.0%

6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate (849101-40-2) + methyl (methyl 2-O-acetyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (849101-43-5) → methyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (849101-44-6)

Guidance literature:

With triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at -20 ℃; for 1h;

DOI:10.1016/j.carres.2004.11.029

Reference yield:

pivaloyl chloride (3282-30-2) → methyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (849101-44-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 41 percent / pyridine / dimethylformamide / 48 h / 45 °C

2: 80 percent / N₂H₄*HOAc / dimethylformamide / 2.5 h / 20 °C

3: 58 percent / Cs₂CO₃ / CH₂Cl₂ / 1 h / 0 °C

4: 40 percent / 3A MS; TESOTf / CH₂Cl₂ / 1 h / -20 °C

With pyridine; triethylsilyl trifluoromethyl sulfonate; hydrazinium monoacetate; caesium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2004.11.029

Reference yield:

1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α,β-D-glucopyranose → methyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside (849101-44-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 41 percent / pyridine / dimethylformamide / 48 h / 45 °C

2: 80 percent / N₂H₄*HOAc / dimethylformamide / 2.5 h / 20 °C

3: 58 percent / Cs₂CO₃ / CH₂Cl₂ / 1 h / 0 °C

4: 40 percent / 3A MS; TESOTf / CH₂Cl₂ / 1 h / -20 °C

With pyridine; triethylsilyl trifluoromethyl sulfonate; hydrazinium monoacetate; caesium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2004.11.029

upstream raw materials:

6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate

methyl (methyl 2-O-acetyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

pivaloyl chloride

methyl dimethylthexylsilyl 2-O-acetyl-4-O-levulinoyl-3-O-pivaloyl-β-L-idopyranosiduronate

Downstream raw materials:

methyl (2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

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