methyl (methyl 2-O-acetyl-4-O-levulinoyl-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 (methyl 2-O-acetyl-4-O-levulinoyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside
CAS No.:849101-49-1
Molecular Formula:C₃₅H₄₇N₃O₁₆
Molecular Weight:765.769
Hs Code.:

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

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

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

There total 3 articles about methyl (methyl 2-O-acetyl-4-O-levulinoyl-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: 75.0%

: 175978-56-0
methyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

: 849101-35-5
methyl 2-O-acetyl-4-O-levulinoyl-3-O-pivaloyl-α-L-idopyranosyluronate trichloroacetimidate

: 849101-49-1
methyl (methyl 2-O-acetyl-4-O-levulinoyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

Guidance literature:: With triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at -20 - -10 ℃; for 3h;
DOI:10.1016/j.carres.2004.11.029

Reference yield:

: 835605-36-2
methyl dimethylthexylsilyl 2-O-acetyl-4-O-levulinoyl-3-O-pivaloyl-β-L-idopyranosiduronate

: 849101-49-1
methyl (methyl 2-O-acetyl-4-O-levulinoyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 64 percent / HOAc; Bu₄NF / tetrahydrofuran / 0 - 20 °C

2: 58 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

3: 75 percent / 4A MS; TESOTf / CH₂Cl₂ / 3 h / -20 - -10 °C

With tetrabutyl ammonium fluoride; triethylsilyl trifluoromethyl sulfonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.carres.2004.11.029

Reference yield:

: methyl 2-O-acetyl-4-O-levulinoyl-3-O-pivaloyl-L-idopyranosuronate

: 849101-49-1
methyl (methyl 2-O-acetyl-4-O-levulinoyl-3-O-pivaloyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 58 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

2: 75 percent / 4A MS; TESOTf / CH₂Cl₂ / 3 h / -20 - -10 °C

With triethylsilyl trifluoromethyl sulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;
DOI:10.1016/j.carres.2004.11.029