2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester

Base Information

• Chemical Name: 2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester
• CAS No.: 858127-20-5
• Molecular Formula: C₃₇H₃₆F₃NO₈
• Molecular Weight: 679.69
• Mol file: 858127-20-5.mol

Synonyms:2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester

Chemical Property of 2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester

There total 1 articles about 2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-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:

Carbonic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl ester methyl ester + 2,2,2-trifluoro-N-phenyl-acetimidoyl chloride (61881-19-4) → 2,2,2-Trifluoro-N-phenyl-acetimidic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester + 2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester (858127-20-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 36h;

DOI:10.1021/jo050301x

Reference yield: 75.0%

2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester (858127-20-5) + (2S,4aR,6S,7R,8R,8aR)-7-Azido-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (858127-25-0) → p-methoxyphenyl 3,4,6-tri-O-benzyl-2-O-methoxycarbonyl-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-azido-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside (858127-26-1)

Guidance literature:

With 5A molecular sieve; In cyclohexane; 1,2-dichloro-ethane; at 20 ℃;

DOI:10.1021/jo050301x

Reference yield:

2,2,2-Trifluoro-N-phenyl-acetimidic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-methoxycarbonyloxy-tetrahydro-pyran-2-yl ester (858127-20-5) → 2-{7-azido-6-[3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol (858127-27-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / 5 Angstroem AW molecular sieves / 1,2-dichloro-ethane; cyclohexane / 20 °C

2: 89 percent / K₂CO₃ / methanol / 8 h / 40 °C

With 5A molecular sieve; potassium carbonate; In methanol; cyclohexane; 1,2-dichloro-ethane;

DOI:10.1021/jo050301x

upstream raw materials:

2,2,2-trifluoro-N-phenyl-acetimidoyl chloride

Downstream raw materials:

p-methoxyphenyl 3,4,6-tri-O-benzyl-2-O-methoxycarbonyl-β-D-galactopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-2-azido-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

2-{7-azido-6-[3,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol