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

Base Information

• Chemical Name: 2,4-dideoxy-3-O-methyl-4-(N-(trifluoroacetyl)-N-ethylamino)-1-phenylsulfinyl-α,β-L-xylopyranose
• CAS No.: 134006-16-9
• Molecular Formula: C₁₆H₂₀F₃NO₄S
• Molecular Weight: 379.4
• Mol file: 134006-16-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 2,4-dideoxy-3-O-methyl-4-(N-(trifluoroacetyl)-N-ethylamino)-1-phenylsulfinyl-α,β-L-xylopyranose 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:

methyl 2,4-dideoxy-3-O-methyl-4-(N-acetylamino)-α,β-L-xylopyranoside (134053-37-5) + thiophenol (108-98-5) + trifluoroacetic anhydride (407-25-0) → 2,4-dideoxy-3-O-methyl-4-(N-(trifluoroacetyl)-N-ethylamino)-1-phenylsulfinyl-α,β-L-xylopyranose (134006-16-9)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/ja00012a069

Reference yield:

2,4-dideoxy-3-O-methyl-4-(N-(trifluoroacetyl)-N-ethylamino)-1-phenylsulfinyl-α,β-L-xylopyranose (134006-16-9) → 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 (134029-28-0)

Guidance literature:

Multi-step reaction with 5 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

5: 90 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

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

methyl 2,4-dideoxy-3-O-methyl-4-(N-acetylamino)-α,β-L-xylopyranoside

thiophenol

trifluoroacetic anhydride

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

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

2,6-Dimethyl-thiobenzoic acid S-((2R,3S,4S,6S)-6-{N-[(2R,3S,4S,5R,6R)-5-((2S,4S,5S)-5-ethylamino-4-methoxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl]aminooxy}-4-hydroxy-2-methyl-tetrahydro-pyran-3-yl) ester