methyl [methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate

Base Information

• Chemical Name: methyl [methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate
• CAS No.: 247077-93-6
• Molecular Formula: C₅₉H₆₃N₃O₁₉
• Molecular Weight: 1118.16

Synonyms:methyl [methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate

Chemical Property of methyl [methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of methyl [methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate

There total 11 articles about methyl [methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate 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%

methyl [methyl (methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate (247077-92-5) → methyl [methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate (247077-93-6)

Guidance literature:

With hydrazine hydrate; In pyridine; acetic acid; at 0 ℃; for 0.25h;

DOI:10.1016/S0968-0896(99)00106-6

Reference yield:

phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside (190367-07-8) → methyl [methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate (247077-93-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluorometanesulfonic acid / CH₂Cl₂ / 0 - 20 °C

2: aqueous trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

3: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

4: 1.26 g / triethylamine / CH₂Cl₂ / 20 °C

5: CrO₃; aq. H₂SO₄ / acetone / 4 h / 0 °C

6: 559.6 mg / ethyl acetate; diethyl ether / 0.17 h

7: benzylamine / diethyl ether / 6 h / 0 °C

8: 383.2 mg / 4 Angstroem molecular sieves; 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.5 h

9: 75 percent / 4 Angstroem molecular sieves; tert-butyldimethylsilyl trifluoromethanesulfonate / toluene / 2 h / -20 °C

10: 90 percent / hydrazine hydrate / pyridine; acetic acid / 0.25 h / 0 °C

With chromium(VI) oxide; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; t-butyldimethylsiyl triflate; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; benzylamine; trifluoroacetic acid; In pyridine; diethyl ether; dichloromethane; acetic acid; ethyl acetate; acetone; toluene; 1: Condensation / 2: Hydrolysis / 3: silylation / 4: Acylation / 5: Hydrolysis / 6: Methylation / 7: Deacetylation / 8: Addition / 9: Condensation / 10: hydrazinolysis;

DOI:10.1016/S0968-0896(99)00106-6

Reference yield:

1-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glucopyranose → methyl [methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate (247077-93-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluorometanesulfonic acid / CH₂Cl₂ / 0 - 20 °C

2: aqueous trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

3: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

4: 1.26 g / triethylamine / CH₂Cl₂ / 20 °C

5: CrO₃; aq. H₂SO₄ / acetone / 4 h / 0 °C

6: 559.6 mg / ethyl acetate; diethyl ether / 0.17 h

7: benzylamine / diethyl ether / 6 h / 0 °C

8: 383.2 mg / 4 Angstroem molecular sieves; 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.5 h

9: 75 percent / 4 Angstroem molecular sieves; tert-butyldimethylsilyl trifluoromethanesulfonate / toluene / 2 h / -20 °C

10: 90 percent / hydrazine hydrate / pyridine; acetic acid / 0.25 h / 0 °C

With chromium(VI) oxide; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; t-butyldimethylsiyl triflate; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; benzylamine; trifluoroacetic acid; In pyridine; diethyl ether; dichloromethane; acetic acid; ethyl acetate; acetone; toluene; 1: Condensation / 2: Hydrolysis / 3: silylation / 4: Acylation / 5: Hydrolysis / 6: Methylation / 7: Deacetylation / 8: Addition / 9: Condensation / 10: hydrazinolysis;

DOI:10.1016/S0968-0896(99)00106-6

upstream raw materials:

methyl [methyl (methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-allyl-3-O-benzyl-α-L-idopyranosid]uronate

phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside

2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-1-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glucopyranose

methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate-(1->4)-1-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glucopyranose

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