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

Base Information

• Chemical Name: methyl O-(benzyl 2-O-benzoyl-4-O-levulinyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside
• CAS No.: 189390-23-6
• Molecular Formula: C₄₈H₅₄O₁₅
• Molecular Weight: 870.948

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about methyl O-(benzyl 2-O-benzoyl-4-O-levulinyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,6-di-O-benzyl-3-O-methyl-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:

levulinic anhydride (40608-06-8) → methyl O-(benzyl 2-O-benzoyl-4-O-levulinyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside (189390-23-6)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h

2: CrO₃, aq. H₂SO₄ / acetone / 3 h / 0 °C

3: 11.6 g / KHCO₃ / dimethylformamide / Ambient temperature

With chromium(VI) oxide; dmap; sulfuric acid; potassium hydrogencarbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm960726z

Reference yield:

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) → methyl O-(benzyl 2-O-benzoyl-4-O-levulinyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside (189390-23-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 79 percent / NaH / dimethylformamide / 1 h

2: 70 percent / HBF₄, NaBH₃CN / tetrahydrofuran; diethyl ether / 1.25 h

3: 89 percent / triflic acid, N-iodosuccinimide, 4A molecular sieves / toluene / 1 h

4: aq. CF₃CO₂H / CH₂Cl₂ / 0.67 h / Ambient temperature

5: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 50 °C

6: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h

7: CrO₃, aq. H₂SO₄ / acetone / 3 h / 0 °C

8: 11.6 g / KHCO₃ / dimethylformamide / Ambient temperature

With chromium(VI) oxide; dmap; N-iodo-succinimide; tetrafluoroboric acid; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; sodium hydride; sodium cyanoborohydride; potassium hydrogencarbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jm960726z

Reference yield:

ethyl 2-O-benzoyl-4,6-O-isopropylidene-3-O-methyl-1-thio-L-idopyranoside → methyl O-(benzyl 2-O-benzoyl-4-O-levulinyl-3-O-methyl-α-L-idopyranosyluronate)-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside (189390-23-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / triflic acid, N-iodosuccinimide, 4A molecular sieves / toluene / 1 h

2: aq. CF₃CO₂H / CH₂Cl₂ / 0.67 h / Ambient temperature

3: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 50 °C

4: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h

5: CrO₃, aq. H₂SO₄ / acetone / 3 h / 0 °C

6: 11.6 g / KHCO₃ / dimethylformamide / Ambient temperature

With chromium(VI) oxide; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; potassium hydrogencarbonate; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jm960726z

upstream raw materials:

benzyl bromide

methyl (2-O-benzoyl-4-O-levulinyl-3-O-methyl-α-L-idopyranosyluronic acid)-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside

levulinic anhydride

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Downstream raw materials:

(2R,3S,4S,5R,6R)-6-((2R,3R,4S,5R)-6-Acetoxy-2-acetoxymethyl-5-benzyloxy-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-methoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

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

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