(benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose

Base Information

Chemical Name:(benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose
CAS No.:200712-66-9
Molecular Formula:C₃₉H₄₆Cl₃NO₁₆
Molecular Weight:891.15
Hs Code.:

Synonyms:(benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose

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Chemical Property of (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose

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Technology Process of (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose

There total 12 articles about (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose 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: 94.0%

: 545-06-2
trichloroacetonitrile

: (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-D-glucopyranose

: 200712-66-9
(benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose

Guidance literature:: With potassium carbonate; In dichloromethane; for 1.5h; Ambient temperature;
DOI:10.1002/(SICI)1521-3773(19981116)37:21<3009::AID-ANIE3009>3.0.CO;2-F

Reference yield:

: 200712-63-6
methyl (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

: 200712-66-9
(benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose

Guidance literature:: Multi-step reaction with 3 steps

1: 67 percent / trifluoroacetic acid; AcOH / 4 h / 60 °C

2: 74 percent / ethanolamine / tetrahydrofuran / 4 h / 16 °C

3: K₂CO₃ / CH₂Cl₂ / 16 h

With potassium carbonate; ethanolamine; acetic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1: Acetylation / 2: deprotection / 3: Addition;
DOI:10.1016/S0008-6215(99)00067-1

Reference yield:

: 19488-48-3
methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

: 200712-66-9
(benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose

Guidance literature:: Multi-step reaction with 11 steps

1: triflic acid; NIS; 4A molecular sieves / toluene / 2 h / -20 °C

2: 86 percent / NaOMe / methanol; CH₂Cl₂ / 1 h

3: 32.1 g / NaH / dimethylformamide / 20 °C

4: 27.5 g / CF₃COOH; water / CH₂Cl₂ / 0.42 h / 20 °C

5: triethylamine; DMAP / CH₂Cl₂ / 3 h / 50 °C

6: 38.5 g / triethylamine; DMAP / CH₂Cl₂

7: CrO₃; H₂SO₄ / acetone / 5 h / 0 °C

8: KHCO₃ / dimethylformamide / 20 °C

9: 67 percent / trifluoroacetic acid; AcOH / 4 h / 60 °C

10: 74 percent / ethanolamine / tetrahydrofuran / 4 h / 16 °C

11: K₂CO₃ / CH₂Cl₂ / 16 h

With chromium(VI) oxide; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; water; sodium methylate; sodium hydride; potassium carbonate; potassium hydrogencarbonate; ethanolamine; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Etherification / 2: debenzoylation / 3: Methylation / 4: Hydrolysis / 5: Etherification / 6: Acylation / 7: Oxidation / 8: Esterification / 9: Acetylation / 10: deprotection / 11: Addition;
DOI:10.1016/S0008-6215(99)00067-1