methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside
CAS No.:904313-19-5
Molecular Formula:C₃₉H₄₁N₃O₁₃
Molecular Weight:759.767
Hs Code.:

Synonyms:methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

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Chemical Property of methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

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Technology Process of methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 7 articles about methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-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: 92.0%

: 123-76-2
levulinic acid

: 697795-88-3
methyl (2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

: 904313-19-5
methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃;
DOI:10.1016/j.carres.2006.02.020

Reference yield:

: 1,4,6-tri-O-acetyl-2-O-benzoyl-3-O-benzyl-L-idopyranose

: 904313-19-5
methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / 0 - 20 °C

2.1: 4 Angstroem molecular sieves / toluene / 0.5 h / 20 °C

2.2: 95 percent / NIS; AgOTf / toluene / 1 h / 0 - 20 °C

3.1: 88 percent / HCl / methanol / 5 h / 20 °C

4.1: TEMPO; Ca(ClO)2; NaHCO₃ / KBr; t-Bu₄NBr / CH₂Cl₂; H₂O / 0 °C

5.1: tetrahydrofuran; diethyl ether / 20 °C

6.1: 92 percent / DCC; DMAP / CH₂Cl₂ / 0 °C

With hydrogenchloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; calcium hypochlorite; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; tetra(n-tert-butyl)ammonium bromide; potassium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene;
DOI:10.1016/j.carres.2006.02.020

Reference yield:

: ethyl 4,6-di-O-acetyl-2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside

: 904313-19-5
methyl (2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyl)uronate-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 4 Angstroem molecular sieves / toluene / 0.5 h / 20 °C

1.2: 95 percent / NIS; AgOTf / toluene / 1 h / 0 - 20 °C

2.1: 88 percent / HCl / methanol / 5 h / 20 °C

3.1: TEMPO; Ca(ClO)2; NaHCO₃ / KBr; t-Bu₄NBr / CH₂Cl₂; H₂O / 0 °C

4.1: tetrahydrofuran; diethyl ether / 20 °C

5.1: 92 percent / DCC; DMAP / CH₂Cl₂ / 0 °C

With hydrogenchloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; calcium hypochlorite; 4 A molecular sieve; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; tetra(n-tert-butyl)ammonium bromide; potassium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene;
DOI:10.1016/j.carres.2006.02.020