benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside

Base Information

• Chemical Name: benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside
• CAS No.: 81086-78-4
• Molecular Formula: C₁₉H₂₇NO₆
• Molecular Weight: 365.426

Synonyms:benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside

Chemical Property of benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside

Chemical Property:

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Technology Process of benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside

There total 2 articles about benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside 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: 88.0%

acetic anhydride (108-24-7) + benzyl 2-deoxy-5,6-O-isopropylidene-2-methylamino-β-D-glucofuranoside (81086-76-2) → benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside (81086-78-4)

Guidance literature:

In methanol; for 0.5h;

DOI:10.1016/S0008-6215(00)80680-1

Reference yield:

benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside (58886-40-1) → benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside (81086-78-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / lithium aluminium hydride / tetrahydrofuran / 19 h / Heating

2: 88 percent / methanol / 0.5 h

With lithium aluminium tetrahydride; In tetrahydrofuran; methanol;

DOI:10.1016/S0008-6215(00)80680-1

Reference yield: 79.0%

L-2-chloropropionic acid (598-78-7,7474-05-7,29617-66-1,62138-52-7) + benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside (81086-78-4) → benzyl 2-(N-acetyl-N-methylamino)-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside (81086-80-8)

Guidance literature:

With sodium hydride; In 1,4-dioxane; 1.) 30 min, 90 deg C; 2.) 1.5 h, 65 deg C;

DOI:10.1016/S0008-6215(00)80680-1

upstream raw materials:

acetic anhydride

benzyl 2-deoxy-5,6-O-isopropylidene-2-methylamino-β-D-glucofuranoside

benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside

Downstream raw materials:

benzyl 2-(N-acetyl-N-methylamino)-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside

benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside

benzyl 2-(N-acetyl-N-methylamino)-2-deoxy-5,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucofuranoside

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