isopropyl O-(2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: isopropyl O-(2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside
• CAS No.: 1420236-27-6
• Molecular Formula: C₅₆H₆₄N₆O₁₅
• Molecular Weight: 1061.16

Synonyms:isopropyl O-(2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside

Chemical Property of isopropyl O-(2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of isopropyl O-(2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside

There total 4 articles about isopropyl O-(2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-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: 91.0%

isopropyl O-(2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(methyl-3-O-benzyl-2-O-pivaloyl-α-L-idopyranosyluronate)-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside (1420236-19-6) → isopropyl O-(2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside (1420236-27-6)

Guidance literature:

isopropyl O-(2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(methyl-3-O-benzyl-2-O-pivaloyl-α-L-idopyranosyluronate)-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside; With dihydrogen peroxide; lithium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 24h;

With potassium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 24h;

DOI:10.1002/chem.201202770

Reference yield:

isopropyl 2-azido-2-deoxy-3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranozide → isopropyl O-(2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside (1420236-27-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium cyanoborohydride; hydrogenchloride / tetrahydrofuran; diethyl ether / 0.17 h / 20 °C / Molecular sieve; Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 20 °C / Inert atmosphere; Molecular sieve

3.1: triethylsilane / dichloromethane / 0.08 h / -78 °C / Inert atmosphere; Molecular sieve

3.2: 0.67 h / -78 - -40 °C / Inert atmosphere

4.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 24 h / 0 - 20 °C

4.2: 24 h / 0 - 20 °C

With hydrogenchloride; triethylsilane; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; sodium cyanoborohydride; lithium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1002/chem.201202770

Reference yield:

O-[methyl 4-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-L-idopyranosyluronate] trichloroacetamidate → isopropyl O-(2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(3-O-benzyl-α-L-idopyranosyluronic acid)-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside (1420236-27-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 20 °C / Inert atmosphere; Molecular sieve

2.1: triethylsilane / dichloromethane / 0.08 h / -78 °C / Inert atmosphere; Molecular sieve

2.2: 0.67 h / -78 - -40 °C / Inert atmosphere

3.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 24 h / 0 - 20 °C

3.2: 24 h / 0 - 20 °C

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; lithium hydroxide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/chem.201202770

upstream raw materials:

isopropyl 2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside

isopropyl O-(2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(methyl-3-O-benzyl-2-O-pivaloyl-α-L-idopyranosyluronate)-(1→4)-2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

C₅₆H₆₈N₂O₂₁S₂

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