Benzoic acid (2R,3R,4S,5S,6R)-3-{(2S,4S,5S)-5-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-5-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5S,6R)-3-{(2S,4S,5S)-5-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-5-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yl ester
• CAS No.: 153693-50-6
• Molecular Formula: C₂₄H₃₂F₃NO₉
• Molecular Weight: 535.515

Synonyms:Benzoic acid (2R,3R,4S,5S,6R)-3-{(2S,4S,5S)-5-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-5-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

Chemical Property of Benzoic acid (2R,3R,4S,5S,6R)-3-{(2S,4S,5S)-5-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-5-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

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Technology Process of Benzoic acid (2R,3R,4S,5S,6R)-3-{(2S,4S,5S)-5-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-5-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yl ester

There total 5 articles about Benzoic acid (2R,3R,4S,5S,6R)-3-{(2S,4S,5S)-5-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-5-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-4-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: 71.0%

benzoyl chloride (98-88-4) + N-[(3S,4S,6S)-6-((2R,3R,4S,5R,6R)-4,5-Dihydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-4-methoxy-tetrahydro-pyran-3-yl]-N-ethyl-2,2,2-trifluoro-acetamide (153693-48-2) → Benzoic acid (2R,3R,4S,5S,6R)-3-{(2S,4S,5S)-5-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-5-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yl ester (153693-50-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 50 ℃; for 4h;

DOI:10.1021/ja00084a018

Reference yield:

methyl 6-deoxy-3,4-O-isopropylidene-β-D-galactopyranoside (39981-26-5) → Benzoic acid (2R,3R,4S,5S,6R)-3-{(2S,4S,5S)-5-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-5-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yl ester (153693-50-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) (Bu₃Sn)2O / 1.) toluene, 70 deg C, 1 h, 2.) Et₂O, from -60 deg C to 0 deg C, 1 h

2: 90 percent / TsOH, H₂O / methanol / 1 h / 25 °C

3: 71 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h / 50 °C

With dmap; water; toluene-4-sulfonic acid; triethylamine; bis(tri-n-butyltin)oxide; In methanol; dichloromethane;

DOI:10.1021/ja00084a018

Reference yield:

2,4-dideoxy-3-O-methyl-4-(N-(trifluoroacetyl)-N-ethylamino)-1-phenylsulfinyl-α,β-L-xylopyranose (134006-16-9) → Benzoic acid (2R,3R,4S,5S,6R)-3-{(2S,4S,5S)-5-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-4-methoxy-tetrahydro-pyran-2-yloxy}-5-hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yl ester (153693-50-6)

Guidance literature:

Multi-step reaction with 4 steps

1: diethyl ether / 0.08 h / -60 °C

2: 1.) (Bu₃Sn)2O / 1.) toluene, 70 deg C, 1 h, 2.) Et₂O, from -60 deg C to 0 deg C, 1 h

3: 90 percent / TsOH, H₂O / methanol / 1 h / 25 °C

4: 71 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h / 50 °C

With dmap; water; toluene-4-sulfonic acid; triethylamine; bis(tri-n-butyltin)oxide; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/ja00084a018

upstream raw materials:

benzoyl chloride

N-[(3S,4S,6S)-6-((2R,3R,4S,5R,6R)-4,5-Dihydroxy-2-methoxy-6-methyl-tetrahydro-pyran-3-yloxy)-4-methoxy-tetrahydro-pyran-3-yl]-N-ethyl-2,2,2-trifluoro-acetamide

methyl 6-deoxy-3,4-O-isopropylidene-β-D-galactopyranoside

2,4-dideoxy-3-O-methyl-4-(N-(trifluoroacetyl)-N-ethylamino)-1-phenylsulfinyl-α,β-L-xylopyranose

Downstream raw materials:

methyl 3-O-benzoyl-6-deoxy-2-O-<2,4-dideoxy-3-O-methyl-4-(N-trifluoroacetyl-N-ethylamino)-α-L-xylopyranosyl>-4-triflyl-β-D-galactopyranoside

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