dimethylthexylsilyl O-(methyl-2-O-levulinoyl-3,4-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-deoxy-2-azido-3-O-benzyl-6-O-acetyl-β-D-glucopyranoside

Base Information

Chemical Name:dimethylthexylsilyl O-(methyl-2-O-levulinoyl-3,4-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-deoxy-2-azido-3-O-benzyl-6-O-acetyl-β-D-glucopyranoside
CAS No.:1577227-91-8
Molecular Formula:C₄₉H₆₅N₃O₁₄Si
Molecular Weight:948.152
Hs Code.:

dimethylthexylsilyl O-(methyl-2-O-levulinoyl-3,4-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-deoxy-2-azido-3-O-benzyl-6-O-acetyl-β-D-glucopyranoside

Synonyms:dimethylthexylsilyl O-(methyl-2-O-levulinoyl-3,4-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-deoxy-2-azido-3-O-benzyl-6-O-acetyl-β-D-glucopyranoside

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Chemical Property of dimethylthexylsilyl O-(methyl-2-O-levulinoyl-3,4-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-deoxy-2-azido-3-O-benzyl-6-O-acetyl-β-D-glucopyranoside

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Technology Process of dimethylthexylsilyl O-(methyl-2-O-levulinoyl-3,4-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-deoxy-2-azido-3-O-benzyl-6-O-acetyl-β-D-glucopyranoside

There total 6 articles about dimethylthexylsilyl O-(methyl-2-O-levulinoyl-3,4-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-deoxy-2-azido-3-O-benzyl-6-O-acetyl-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: 61.0%

: 1577227-92-9
C₂₈H₃₀Cl₃NO₉

: dimethylthexylsilyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

: 1577227-91-8
dimethylthexylsilyl O-(methyl-2-O-levulinoyl-3,4-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-deoxy-2-azido-3-O-benzyl-6-O-acetyl-β-D-glucopyranoside

Guidance literature:: C₂₈H₃₀Cl₃NO₉; dimethylthexylsilyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside; In dichloromethane; toluene; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With trifluorormethanesulfonic acid; In tetrahydrofuran; toluene; at -30 ℃; Molecular sieve; Inert atmosphere;
DOI:10.1039/c3ob42312c

Reference yield:

: 1577227-58-7
dimethylthexylsilyl 3-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside

: 1577227-91-8
dimethylthexylsilyl O-(methyl-2-O-levulinoyl-3,4-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-deoxy-2-azido-3-O-benzyl-6-O-acetyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: dichloromethane / 1 h / 20 °C / Molecular sieve; Inert atmosphere

1.2: 1 h / -78 °C / Molecular sieve; Inert atmosphere

1.3: Molecular sieve; Inert atmosphere

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 20 °C / Inert atmosphere

3.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

4.1: pyridine hydrogenfluoride / tetrahydrofuran / 18 h / Inert atmosphere

5.1: sodium hydride / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

6.1: dichloromethane; toluene / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

6.2: -30 °C / Molecular sieve; Inert atmosphere

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydride; pyridine hydrogenfluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1039/c3ob42312c

Reference yield:

: 1577228-10-4
dimethylthexylsilyl 3,4-O-benzyl-β-D-glucopyranoside

: 1577227-91-8
dimethylthexylsilyl O-(methyl-2-O-levulinoyl-3,4-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-O-2-deoxy-2-azido-3-O-benzyl-6-O-acetyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 20 °C / Inert atmosphere

2.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

3.1: pyridine hydrogenfluoride / tetrahydrofuran / 18 h / Inert atmosphere

4.1: sodium hydride / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

5.1: dichloromethane; toluene / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

5.2: -30 °C / Molecular sieve; Inert atmosphere

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydride; pyridine hydrogenfluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1039/c3ob42312c