methyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

Base Information

• Chemical Name: methyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate
• CAS No.: 273400-92-3
• Molecular Formula: C₅₈H₅₇NO₂₃
• Molecular Weight: 1136.08

Synonyms:methyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

Chemical Property of methyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

Chemical Property:

Purity/Quality:

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Technology Process of methyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

There total 8 articles about methyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)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: 80.0%

methyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-4,6-O-benzylidene-2-deoxy-2-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate → methyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate (273400-92-3)

Guidance literature:

With water; acetic acid; at 100 ℃; for 0.5h;

DOI:10.1016/S0008-6215(99)00322-5

Reference yield:

methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate (169557-85-1) → methyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate (273400-92-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / N-iodosuccinimide; 4 Angstroem molecular sieves; Me₃SiOTf / CH₂Cl₂ / 1 h / 20 °C

2: 360 mg / AcCl / methanol; CH₂Cl₂ / 24 h / 20 °C

3: 327 mg / CF₃COOH / 1.5 h / 20 °C

4: 85 percent / 4 Angstroem molecular sieves; Me₃SiOTf / toluene / 2 h / 20 °C

5: 82 percent / Bu₃SnH; AIBN / benzene; N,N-dimethyl-acetamide / 3 h / 20 - 80 °C

6: 80 percent / AcOH; water / 0.5 h / 100 °C

With N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; water; tri-n-butyl-tin hydride; acetic acid; acetyl chloride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl acetamide; toluene; benzene; 1: Etherification / 2: Deacetylation / 3: Etherification / 4: Etherification / 5: Reduction / 6: Hydrolysis;

DOI:10.1016/S0008-6215(99)00322-5

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-galactopyranoside (198200-67-8) → methyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate (273400-92-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 76 percent / N-iodosuccinimide; 4 Angstroem molecular sieves; Me₃SiOTf / CH₂Cl₂ / 1 h / 20 °C

2: 360 mg / AcCl / methanol; CH₂Cl₂ / 24 h / 20 °C

3: 327 mg / CF₃COOH / 1.5 h / 20 °C

4: 85 percent / 4 Angstroem molecular sieves; Me₃SiOTf / toluene / 2 h / 20 °C

5: 82 percent / Bu₃SnH; AIBN / benzene; N,N-dimethyl-acetamide / 3 h / 20 - 80 °C

6: 80 percent / AcOH; water / 0.5 h / 100 °C

With N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; water; tri-n-butyl-tin hydride; acetic acid; acetyl chloride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl acetamide; toluene; benzene; 1: Etherification / 2: Deacetylation / 3: Etherification / 4: Etherification / 5: Reduction / 6: Hydrolysis;

DOI:10.1016/S0008-6215(99)00322-5

upstream raw materials:

methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-galactopyranoside

(2S,3S,4S,5R,6R)-4,5-Bis-benzoyloxy-3-[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-2-yloxy]-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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

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