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

Base Information

Chemical Name: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
CAS No.:247077-92-5
Molecular Formula:C₆₄H₆₉N₃O₂₁
Molecular Weight:1216.26
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 11 articles about 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 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: 75.0%

: 181024-57-7
methyl (methyl 2-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate

: 247077-91-4
(2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R)-5-Azido-4-benzyloxy-2-benzyloxymethyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzoyloxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 247077-92-5
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

Guidance literature:: With 4 A molecular sieve; t-butyldimethylsiyl triflate; In toluene; at -20 ℃; for 2h;
DOI:10.1016/S0968-0896(99)00106-6

Reference yield:

: 40608-06-8
levulinic anhydride

: 247077-92-5
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

Guidance literature:: Multi-step reaction with 6 steps

1: 1.26 g / triethylamine / CH₂Cl₂ / 20 °C

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

3: 559.6 mg / ethyl acetate; diethyl ether / 0.17 h

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

5: 383.2 mg / 4 Angstroem molecular sieves; 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.5 h

6: 75 percent / 4 Angstroem molecular sieves; tert-butyldimethylsilyl trifluoromethanesulfonate / toluene / 2 h / -20 °C

With chromium(VI) oxide; 4 A molecular sieve; sulfuric acid; t-butyldimethylsiyl triflate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; benzylamine; In diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; 1: Acylation / 2: Hydrolysis / 3: Methylation / 4: Deacetylation / 5: Addition / 6: Condensation;
DOI:10.1016/S0968-0896(99)00106-6

Reference yield:

: 190367-07-8
phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside

: 247077-92-5
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

Guidance literature:: Multi-step reaction with 9 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

With chromium(VI) oxide; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; t-butyldimethylsiyl triflate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; benzylamine; trifluoroacetic acid; In diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; 1: Condensation / 2: Hydrolysis / 3: silylation / 4: Acylation / 5: Hydrolysis / 6: Methylation / 7: Deacetylation / 8: Addition / 9: Condensation;
DOI:10.1016/S0968-0896(99)00106-6