2-naphthylmethyl O-(methyl 2,3-O-isopropylidene-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Base Information

Chemical Name:2-naphthylmethyl O-(methyl 2,3-O-isopropylidene-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside
CAS No.:890131-34-7
Molecular Formula:C₄₁H₄₄Cl₃NO₁₄
Molecular Weight:881.158
Hs Code.:

2-naphthylmethyl O-(methyl 2,3-O-isopropylidene-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Synonyms:2-naphthylmethyl O-(methyl 2,3-O-isopropylidene-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

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Chemical Property of 2-naphthylmethyl O-(methyl 2,3-O-isopropylidene-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

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Technology Process of 2-naphthylmethyl O-(methyl 2,3-O-isopropylidene-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

There total 8 articles about 2-naphthylmethyl O-(methyl 2,3-O-isopropylidene-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 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%

: 896729-54-7
2-naphthylmethyl O-(methyl 2,3-O-isopropylidene-β-D-glucopyranosyluronate)-(1->3)-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

: 123-76-2
levulinic acid

: 890131-34-7
2-naphthylmethyl O-(methyl 2,3-O-isopropylidene-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 1h;
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

: 890131-34-7
2-naphthylmethyl O-(methyl 2,3-O-isopropylidene-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 6 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

With dmap; trimethylsilyl bromide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium methylate; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,4,6-trimethyl-pyridine; In methanol; dichloromethane; 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

: 890131-34-7
2-naphthylmethyl O-(methyl 2,3-O-isopropylidene-4-O-levulinoyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 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

With dmap; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/anie.200503551