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

Base Information

Chemical Name: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
CAS No.:189390-22-5
Molecular Formula:C₄₁H₄₈O₁₅
Molecular Weight:780.823
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 9 articles about 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 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:

: 189390-21-4
methyl O-[2-O-benzoyl-4-O-levulinyl-3-O-methyl-6-O-(tert-butyldimethylsilyl)-α-L-idopyranosyl]-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-glucopyranoside

: 189390-22-5
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

Guidance literature:: With chromium(VI) oxide; sulfuric acid; In acetone; at 0 ℃; for 3h; Yield given;
DOI:10.1021/jm960726z

Reference yield:

: 40608-06-8
levulinic anhydride

: 189390-22-5
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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With chromium(VI) oxide; dmap; sulfuric acid; triethylamine; In dichloromethane; acetone;
DOI:10.1021/jm960726z

Reference yield:

: 76375-66-1
methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

: 189390-22-5
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

Guidance literature:: Multi-step reaction with 7 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

With chromium(VI) oxide; dmap; N-iodo-succinimide; tetrafluoroboric acid; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; sodium hydride; sodium cyanoborohydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/jm960726z