4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-[(2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-4-yloxy]-5-azido-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-[(2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-4-yloxy]-5-azido-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 870543-53-6
• Molecular Formula: C₄₀H₄₇N₃O₁₂
• Molecular Weight: 761.826

Synonyms:4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-[(2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-4-yloxy]-5-azido-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of 4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-[(2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-4-yloxy]-5-azido-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of 4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-[(2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-4-yloxy]-5-azido-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester

There total 1 articles about 4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-[(2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-4-yloxy]-5-azido-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl 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: 90.0%

p-methoxyphenyl 2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside (870543-37-6) + (3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate (870543-35-4) → 4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-[(2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-4-yloxy]-5-azido-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester (870543-53-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/anie.200502615

Reference yield: 100.0%

4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-[(2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-4-yloxy]-5-azido-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester (870543-53-6) → Acetic acid (2S,3R,4R,5S,6S)-4-((2S,3R,4S,5R,6R)-5-azido-4-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-3-yl ester (870543-50-3)

Guidance literature:

With hydrazinium monoacetate; In methanol; dichloromethane; at 25 ℃; for 12h;

DOI:10.1002/anie.200502615

Reference yield:

4-Oxo-pentanoic acid (2S,3R,4S,5R,6R)-2-[(2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-4-yloxy]-5-azido-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester (870543-53-6) → Acetic acid (3R,4R,5S,6S)-4-((2S,3R,4S,5R,6R)-5-azido-4-benzyloxy-3-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / hydrazinium acetate / CH₂Cl₂; methanol / 12 h / 25 °C

2: 73 percent / silver(I) oxide; dimethyl sulfide / tetrahydrofuran / 8 h / 25 °C

3: cerium(IV) ammonium nitrate / acetonitrile; H₂O / 1.5 h / 25 °C

With ammonium cerium(IV) nitrate; dimethylsulfide; hydrazinium monoacetate; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;

DOI:10.1002/anie.200502615

upstream raw materials:

p-methoxyphenyl 2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

(3R,4S,5R,6R)-2-(2,2,2-trichloroacetimidoyloxy)-5-azido-4-benzyloxytetrahydro-6-methyl-2H-pyran-3-yl 4-oxopentanoate

Downstream raw materials:

Acetic acid (2S,3R,4R,5S,6S)-4-((2S,3R,4S,5R,6R)-5-azido-4-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-2-(4-methoxy-phenoxy)-6-methyl-tetrahydro-pyran-3-yl ester

4-methoxyphenyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate

4-penten-1-yl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

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