O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose

Base Information

Chemical Name:O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose
CAS No.:890131-38-1
Molecular Formula:C₄₀H₃₈Cl₈N₂O₁₈
Molecular Weight:1118.37
Hs Code.:

O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose

Synonyms:O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose

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Chemical Property of O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose

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Technology Process of O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose

There total 13 articles about O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose 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: 68.0%

: (2S,4S,5R,6R)-4,5-Bis-benzoyloxy-6-[(2R,3R,4R,5R)-3-(2-chloro-acetoxy)-2-(2-chloro-acetoxymethyl)-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yloxy]-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 545-06-2
trichloroacetonitrile

: 890131-38-1
O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 0.333333h;
DOI:10.1002/anie.200503551

Reference yield:

: O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-1,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-D-galactopyranose

: 890131-38-1
O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose

Guidance literature:: Multi-step reaction with 12 steps

1: 89 percent / n-Bu₄NBr; BF₃*Et₂O; TMSBr / 2,4,6-collidine / CH₂Cl₂ / 48 h / 20 °C

2: 90 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h

3: NaOMe / methanol

4: trifluoroacetic acid / 4 h

5: 83 percent / camphorsulfonic acid / dimethylformamide / 1.5 h

6: 92 percent / N,N-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h

7: 79 percent / AcOH / CH₂Cl₂; H₂O / 24 h / 20 °C

8: 95 percent / pyridine / 1 h / 0 °C

9: AcOH / 0.5 h / 100 °C

10: pyridine / CH₂Cl₂ / 1 h / 0 °C

11: 2,3-dichloro-5,6-dicyanobenzoquinone / CH₂Cl₂; methanol / 24 h / 20 °C

12: 68 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.33 h

With pyridine; dmap; trimethylsilyl bromide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-trimethyl-pyridine; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/anie.200503551

Reference yield:

: 890131-32-5
O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-2-trichloromethyl-(4,6-di-O-acetyl-1,2-dideoxy-α-D-galactopyrano)[2,1-d]2-oxazoline

: 890131-38-1
O-(methyl 2,3-di-O-benzoyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-di-O-chloroacetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose

Guidance literature:: Multi-step reaction with 11 steps

1: 90 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h

2: NaOMe / methanol

3: trifluoroacetic acid / 4 h

4: 83 percent / camphorsulfonic acid / dimethylformamide / 1.5 h

5: 92 percent / N,N-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h

6: 79 percent / AcOH / CH₂Cl₂; H₂O / 24 h / 20 °C

7: 95 percent / pyridine / 1 h / 0 °C

8: AcOH / 0.5 h / 100 °C

9: pyridine / CH₂Cl₂ / 1 h / 0 °C

10: 2,3-dichloro-5,6-dicyanobenzoquinone / CH₂Cl₂; methanol / 24 h / 20 °C

11: 68 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.33 h

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/anie.200503551