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

Base Information

• Chemical Name: methyl (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 200712-63-6
• Molecular Formula: C₄₈H₅₆O₁₄
• Molecular Weight: 856.964

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 9 articles about methyl (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-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:

benzyl bromide (100-39-0) + (2R,3S,4S,5R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid (200712-62-5) → methyl (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (200712-63-6)

Guidance literature:

With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0008-6215(99)00067-1

Reference yield:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → methyl (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (200712-63-6)

Guidance literature:

Multi-step reaction with 8 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

With chromium(VI) oxide; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; water; sodium methylate; sodium hydride; potassium hydrogencarbonate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Etherification / 2: debenzoylation / 3: Methylation / 4: Hydrolysis / 5: Etherification / 6: Acylation / 7: Oxidation / 8: Esterification;

DOI:10.1016/S0008-6215(99)00067-1

Reference yield:

ethyl 2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-1-thio-L-idopyranoside → methyl (benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (200712-63-6)

Guidance literature:

Multi-step reaction with 8 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

With chromium(VI) oxide; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; water; sodium methylate; sodium hydride; potassium hydrogencarbonate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Etherification / 2: debenzoylation / 3: Methylation / 4: Hydrolysis / 5: Etherification / 6: Acylation / 7: Oxidation / 8: Esterification;

DOI:10.1016/S0008-6215(99)00067-1

upstream raw materials:

benzyl bromide

(2R,3S,4S,5R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid

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

methyl(2,3-di-O-methyl-α-L-idopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

(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

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

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

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