Benzoic acid (2S,3R,4R,5S,6S)-6-[(2S,3S,4S,5R,6R)-2-benzenesulfonylamino-3-iodo-5-(4-methoxy-benzyloxy)-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4R,5S,6S)-6-[(2S,3S,4S,5R,6R)-2-benzenesulfonylamino-3-iodo-5-(4-methoxy-benzyloxy)-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 210427-12-6
• Molecular Formula: C₅₆H₇₀INO₁₂SSi
• Molecular Weight: 1136.23

Synonyms:Benzoic acid (2S,3R,4R,5S,6S)-6-[(2S,3S,4S,5R,6R)-2-benzenesulfonylamino-3-iodo-5-(4-methoxy-benzyloxy)-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3R,4R,5S,6S)-6-[(2S,3S,4S,5R,6R)-2-benzenesulfonylamino-3-iodo-5-(4-methoxy-benzyloxy)-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2S,3R,4R,5S,6S)-6-[(2S,3S,4S,5R,6R)-2-benzenesulfonylamino-3-iodo-5-(4-methoxy-benzyloxy)-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester

There total 4 articles about Benzoic acid (2S,3R,4R,5S,6S)-6-[(2S,3S,4S,5R,6R)-2-benzenesulfonylamino-3-iodo-5-(4-methoxy-benzyloxy)-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-2-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: 88.0%

benzenesulfonamide (98-10-2) + Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3S,4R)-3-(4-methoxy-benzyloxy)-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester (322648-43-1) → Benzoic acid (2S,3R,4R,5S,6S)-6-[(2S,3S,4S,5R,6R)-2-benzenesulfonylamino-3-iodo-5-(4-methoxy-benzyloxy)-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester (210427-12-6)

Guidance literature:

benzenesulfonamide; Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3S,4R)-3-(4-methoxy-benzyloxy)-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester; In dichloromethane; at 20 ℃; for 0.25h;

With iodonium(di-γ-collidine) perchlorate; In dichloromethane; at 0 ℃; for 1h; Further stages.;

DOI:10.1021/ja0022730

Reference yield:

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose (137915-37-8) → Benzoic acid (2S,3R,4R,5S,6S)-6-[(2S,3S,4S,5R,6R)-2-benzenesulfonylamino-3-iodo-5-(4-methoxy-benzyloxy)-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester (210427-12-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 55 percent / AgClO₄; di-tert-butylpyridine; 4A MS / SnCl₂ / diethyl ether

2.1: 83 percent / NaH / dimethylformamide / 1.5 h / 20 °C

3.1: 4A MS / CH₂Cl₂ / 0.25 h / 20 °C

3.2: 88 percent / I(sym-coll)2ClO₄ / CH₂Cl₂ / 1 h / 0 °C

With silver perchlorate; sodium hydride; Di-tert-butylpyridine; tin(ll) chloride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0022730

Reference yield:

fluoro-4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α/β-L-galactopyranose (142800-26-8) → Benzoic acid (2S,3R,4R,5S,6S)-6-[(2S,3S,4S,5R,6R)-2-benzenesulfonylamino-3-iodo-5-(4-methoxy-benzyloxy)-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-2-methyl-tetrahydro-pyran-3-yl ester (210427-12-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 55 percent / AgClO₄; di-tert-butylpyridine; 4A MS / SnCl₂ / diethyl ether

2.1: 83 percent / NaH / dimethylformamide / 1.5 h / 20 °C

3.1: 4A MS / CH₂Cl₂ / 0.25 h / 20 °C

3.2: 88 percent / I(sym-coll)2ClO₄ / CH₂Cl₂ / 1 h / 0 °C

With silver perchlorate; sodium hydride; Di-tert-butylpyridine; tin(ll) chloride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0022730

upstream raw materials:

benzenesulfonamide

Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-[(2R,3S,4R)-3-(4-methoxy-benzyloxy)-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

fluoro-4-O-benzoyl-6-deoxy-2,3-di-O-benzyl-α/β-L-galactopyranose

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