methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate
CAS No.:1448263-58-8
Molecular Formula:C₄₂H₅₅Cl₃N₄O₁₄Si
Molecular Weight:974.362
Hs Code.:

methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

Synonyms:methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

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Chemical Property of methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

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Technology Process of methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

There total 8 articles about methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate 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:

: C₄₀H₅₅N₃O₁₄Si

: 545-06-2
trichloroacetonitrile

: 1448263-58-8
methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 12h; Inert atmosphere;
DOI:10.1021/ja4027727

Reference yield:

: 87326-81-6
methyl 4-O-acetyl-3-O-benzyl-β-L-idopyranuronate 1,2-(methyl orthoacetate)

: 1448263-58-8
methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium methylate / methanol / -10 - 5 °C / Inert atmosphere

2.1: pyridine / -10 - 0 °C / Inert atmosphere

3.1: dichloromethane / 0.25 h / 20 °C / Inert atmosphere; Molecular sieve

3.2: Inert atmosphere; Molecular sieve

4.1: dichloromethane / 0.5 h / -10 - 20 °C / Inert atmosphere; Molecular sieve

4.2: 0.5 h / -30 °C / Inert atmosphere; Molecular sieve

5.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 12 h / 0 °C / Inert atmosphere

With pyridine; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja4027727

Reference yield:

: 87326-79-2
methyl 1,2,4-tri-O-acetyl-3-O-benzyl-β-L-idopyranosyluronate

: 1448263-58-8
methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate-(1→4)-2-azido-3-O-benzyl-6-O-levulinoyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 7 steps

1.1: titanium(IV) bromide / dichloromethane / 16 h / 20 °C / Darkness; Inert atmosphere

1.2: 14 h / 20 °C / Inert atmosphere

2.1: sodium methylate / methanol / -10 - 5 °C / Inert atmosphere

3.1: pyridine / -10 - 0 °C / Inert atmosphere

4.1: dichloromethane / 0.25 h / 20 °C / Inert atmosphere; Molecular sieve

4.2: Inert atmosphere; Molecular sieve

5.1: dichloromethane / 0.5 h / -10 - 20 °C / Inert atmosphere; Molecular sieve

5.2: 0.5 h / -30 °C / Inert atmosphere; Molecular sieve

6.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 12 h / 0 °C / Inert atmosphere

With pyridine; tetrabutyl ammonium fluoride; sodium methylate; titanium(IV) bromide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja4027727