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

Base Information

Chemical Name: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
CAS No.:189390-19-0
Molecular Formula:C₄₃H₄₈O₁₃
Molecular Weight:772.846
Hs Code.:

Synonyms: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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Chemical Property of 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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Technology Process of 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

There total 11 articles about 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 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: 90.0%

: 189390-23-6
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

: 189390-19-0
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

Guidance literature:: With hydrazine; In pyridine; acetic acid; at 0 ℃; for 1.5h;
DOI:10.1016/S0960-894X(97)00361-2

Reference yield:

: 100-39-0
benzyl bromide

: 189390-19-0
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

Guidance literature:: Multi-step reaction with 2 steps

1: 11.6 g / KHCO₃ / dimethylformamide / Ambient temperature

2: H₂NNH₂, pyridine, AcOH / 0.5 h / 0 °C

With pyridine; potassium hydrogencarbonate; acetic acid; hydrazine; In N,N-dimethyl-formamide;
DOI:10.1021/jm960726z

Reference yield:

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

: 189390-19-0
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

Guidance literature:: Multi-step reaction with 9 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

9: H₂NNH₂, pyridine, AcOH / 0.5 h / 0 °C

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