Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-methyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-methyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 870543-52-5
• Molecular Formula: C₅₅H₆₀O₁₂
• Molecular Weight: 913.074

Synonyms:Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-methyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-methyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-methyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-6-methyl-tetrahydro-pyran-3-yl ester

There total 3 articles about Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-methyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-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: 91.0%

4-penten-1-yl 3,4-di-O-benzyl-α-L-rhamnopyranoside (870543-39-8) + 2-O-acetyl-4-O-benzyl-3-O-(fluorenylmethoxycarbonyl)-α-L-rhamnopyranosyl trichloroacetimidate (870543-38-7) → Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-methyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-6-methyl-tetrahydro-pyran-3-yl ester (870543-52-5)

Guidance literature:

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

DOI:10.1002/anie.200502615

Reference yield:

2-O-acetyl-4-O-benzyl-3-O-(fluorenylmethoxycarbonyl)-α-L-rhamnopyranose → Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-methyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-6-methyl-tetrahydro-pyran-3-yl ester (870543-52-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / sodium hydride / CH₂Cl₂ / 1 h / 25 °C

2: 91 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; sodium hydride; In dichloromethane;

DOI:10.1002/anie.200502615

Reference yield:

4-methoxyphenyl 2-O-acetyl-4-O-benzyl-3-O-(fluorenylmethoxycarbonyl)-α-L-rhamnopyranoside (870543-49-0) → Acetic acid (2S,3R,4R,5S,6S)-5-benzyloxy-2-((2R,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-methyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-6-methyl-tetrahydro-pyran-3-yl ester (870543-52-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O; toluene / 1.33 h / 20 °C

2: 94 percent / sodium hydride / CH₂Cl₂ / 1 h / 25 °C

3: 91 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / 0 °C

With ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; sodium hydride; In dichloromethane; water; toluene; acetonitrile;

DOI:10.1002/anie.200502615

upstream raw materials:

4-penten-1-yl 3,4-di-O-benzyl-α-L-rhamnopyranoside

2-O-acetyl-4-O-benzyl-3-O-(fluorenylmethoxycarbonyl)-α-L-rhamnopyranosyl trichloroacetimidate

4-methoxyphenyl 2-O-acetyl-4-O-benzyl-3-O-(fluorenylmethoxycarbonyl)-α-L-rhamnopyranoside

Downstream raw materials:

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

4-penten-1-yl 2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

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