4-benzoyloxy-5-chloroacetoxy-6-[2-chloroacetoxymethyl-3-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yloxy]-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: 4-benzoyloxy-5-chloroacetoxy-6-[2-chloroacetoxymethyl-3-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yloxy]-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 896729-86-5
• Molecular Formula: C₄₂H₄₂Cl₅NO₁₇
• Molecular Weight: 1010.06

Synonyms:4-benzoyloxy-5-chloroacetoxy-6-[2-chloroacetoxymethyl-3-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yloxy]-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of 4-benzoyloxy-5-chloroacetoxy-6-[2-chloroacetoxymethyl-3-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yloxy]-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of 4-benzoyloxy-5-chloroacetoxy-6-[2-chloroacetoxymethyl-3-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yloxy]-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 11 articles about 4-benzoyloxy-5-chloroacetoxy-6-[2-chloroacetoxymethyl-3-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yloxy]-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 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:

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 → 4-benzoyloxy-5-chloroacetoxy-6-[2-chloroacetoxymethyl-3-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yloxy]-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (896729-86-5)

Guidance literature:

Multi-step reaction with 11 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: 80 percent / pyridine / 6 h / 20 °C

9: 95 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

10: AcOH / 0.33 h / 100 °C

11: 393 mg / pyridine / CH₂Cl₂ / 0.5 h / -20 °C

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

DOI:10.1002/anie.200503551

Reference yield:

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 (890131-32-5) → 4-benzoyloxy-5-chloroacetoxy-6-[2-chloroacetoxymethyl-3-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yloxy]-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (896729-86-5)

Guidance literature:

Multi-step reaction with 10 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: 80 percent / pyridine / 6 h / 20 °C

8: 95 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

9: AcOH / 0.33 h / 100 °C

10: 393 mg / pyridine / CH₂Cl₂ / 0.5 h / -20 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/anie.200503551

Reference yield:

(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-[(2R,3R,4R,5R,6R)-3-hydroxy-2-hydroxymethyl-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester → 4-benzoyloxy-5-chloroacetoxy-6-[2-chloroacetoxymethyl-3-hydroxy-6-(naphthalen-2-ylmethoxy)-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yloxy]-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (896729-86-5)

Guidance literature:

Multi-step reaction with 8 steps

1: trifluoroacetic acid / 4 h

2: 83 percent / camphorsulfonic acid / dimethylformamide / 1.5 h

3: 92 percent / N,N-dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h

4: 79 percent / AcOH / CH₂Cl₂; H₂O / 24 h / 20 °C

5: 80 percent / pyridine / 6 h / 20 °C

6: 95 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

7: AcOH / 0.33 h / 100 °C

8: 393 mg / pyridine / CH₂Cl₂ / 0.5 h / -20 °C

With pyridine; dmap; camphor-10-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/anie.200503551

upstream raw materials:

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

(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-[(2S,4aR,6R,7R,8R,8aR)-6-(naphthalen-2-ylmethoxy)-2-phenyl-7-(2,2,2-trichloro-acetylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

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

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

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