methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate

Base Information

• Chemical Name: methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate
• CAS No.: 275824-46-9
• Molecular Formula: C₃₇H₃₆Cl₆N₂O₁₇
• Molecular Weight: 993.414

Synonyms:methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate

Chemical Property of methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate

Chemical Property:

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Technology Process of methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate

There total 2 articles about methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate 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:

trichloroacetonitrile (545-06-2) + (2S,3S,4S,5R)-4,5-Bis-benzoyloxy-3-[(2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-2-yloxy]-6-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester → methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate (275824-46-9)

Guidance literature:

With 1,5-Diazabicyclo[5.4.0]undec-5-ene; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0008-6215(00)00032-X

Reference yield:

methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate (273401-00-6) → methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate (275824-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / ceric ammonium nitrate / toluene; acetonitrile; H₂O / 0.75 h / 20 °C

2: 232 mg / 1,8-diazabicyclo[4,5,0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

With ammonium cerium(IV) nitrate; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In dichloromethane; water; toluene; acetonitrile; 1: Elimination / 2: Substitution;

DOI:10.1016/S0008-6215(00)00032-X

Reference yield: 50.0%

methyl (4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate + methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate (275824-46-9) → methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β.. (275824-49-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 ℃;

DOI:10.1016/S0008-6215(00)00032-X

upstream raw materials:

trichloroacetonitrile

methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

Downstream raw materials:

methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β..

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