methyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate

Base Information

• Chemical Name: methyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate
• CAS No.: 321380-47-6
• Molecular Formula: C₄₆H₄₈Cl₃NO₁₄
• Molecular Weight: 945.244

Synonyms:methyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate

Chemical Property of methyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate

Chemical Property:

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Safty Information:

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Technology Process of methyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate

There total 19 articles about methyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)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: 60.0%

methyl (methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate (321380-28-3) + 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose (321380-43-2) → Acetic acid (2R,3R,4R,5R,6R)-4-benzyloxy-2-benzyloxymethyl-5,6-bis-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-3-yl ester + methyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate (321380-47-6)

Guidance literature:

methyl (methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate; 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose; With 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1h;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; toluene; at -15 ℃; for 0.166667h;

DOI:10.1016/S0008-6215(00)00234-2

Reference yield:

methyl 3-O-benzyl-α-L-idopyranoside (181228-42-2) → methyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate (321380-47-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 87 percent / 10-D,L-camphorsulfonic acid / dimethylformamide / 3 h / 0 °C

2.1: 2.25 g / pyridine / 0.5 h / 20 °C

3.1: acetic acid; H₂O / 0.25 h / 80 °C

4.1: 2.55 g / imidazole / dimethylformamide / 18 h / 50 °C

5.1: 1.91 g / CrO₃ / aq. H₂SO₄ / 0 °C

6.1: 1.55 g / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

7.1: 60 percent / Bu₄NF / tetrahydrofuran / 0.33 h / 0 °C

8.1: 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

8.2: 60 percent / Me₃SiOTf / CH₂Cl₂; toluene / 0.17 h / -15 °C

With 1H-imidazole; chromium(VI) oxide; dmap; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; sulfuric acid; water; acetic acid; N,N-dimethyl-formamide; 5.1: Jones oxidation;

DOI:10.1016/S0008-6215(00)00234-2

Reference yield:

methyl 2,4,6-tri-O-benzoyl-3-O-benzyl-α-L-idopyranoside (181024-52-2) → methyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate (321380-47-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / NaOMe / methanol / 4 h / 20 °C

2.1: 87 percent / 10-D,L-camphorsulfonic acid / dimethylformamide / 3 h / 0 °C

3.1: 2.25 g / pyridine / 0.5 h / 20 °C

4.1: acetic acid; H₂O / 0.25 h / 80 °C

5.1: 2.55 g / imidazole / dimethylformamide / 18 h / 50 °C

6.1: 1.91 g / CrO₃ / aq. H₂SO₄ / 0 °C

7.1: 1.55 g / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 °C

8.1: 60 percent / Bu₄NF / tetrahydrofuran / 0.33 h / 0 °C

9.1: 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

9.2: 60 percent / Me₃SiOTf / CH₂Cl₂; toluene / 0.17 h / -15 °C

With 1H-imidazole; chromium(VI) oxide; dmap; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; sulfuric acid; water; acetic acid; N,N-dimethyl-formamide; 6.1: Jones oxidation;

DOI:10.1016/S0008-6215(00)00234-2

upstream raw materials:

methyl (methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate

4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose

methyl 3-O-benzyl-α-L-idopyranoside

methyl 2,4,6-tri-O-benzoyl-3-O-benzyl-α-L-idopyranoside

Downstream raw materials:

(2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

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