N-((4aR,6S,7R,8R,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-2,2,2-trifluoro-acetamide

Base Information

• Chemical Name: N-((4aR,6S,7R,8R,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-2,2,2-trifluoro-acetamide
• CAS No.: 177361-89-6
• Molecular Formula: C₂₂H₂₁F₃N₄O₅
• Molecular Weight: 478.428
• Mol file: 177361-89-6.mol

Synonyms:N-((4aR,6S,7R,8R,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-2,2,2-trifluoro-acetamide

Chemical Property of N-((4aR,6S,7R,8R,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-2,2,2-trifluoro-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((4aR,6S,7R,8R,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-2,2,2-trifluoro-acetamide

There total 4 articles about N-((4aR,6S,7R,8R,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-2,2,2-trifluoro-acetamide 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: 52.0%

Methanesulfonic acid (4aR,6S,7R,8R,8aR)-6-benzyloxy-2-phenyl-7-(2,2,2-trifluoro-acetylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester → N-((4aR,6S,7R,8R,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-2,2,2-trifluoro-acetamide (177361-89-6)

Guidance literature:

With sodium azide; tetra(n-butyl)ammonium hydrogensulfate; In N,N-dimethyl-formamide; at 80 ℃; for 36h;

DOI:10.1080/07328309608005660

Reference yield:

benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside (13347-83-6) → N-((4aR,6S,7R,8R,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-2,2,2-trifluoro-acetamide (177361-89-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 12 h

2: 89 percent / pyridine / 0 °C

3: 52 percent / NaN₃, Bu₄NHSO₄ / dimethylformamide / 36 h / 80 °C

With pyridine; sodium azide; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/07328309608005660

Reference yield:

benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside (13343-63-0) → N-((4aR,6S,7R,8R,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-2,2,2-trifluoro-acetamide (177361-89-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / 90percent NH₂NH₂*H₂O / 12 h / 130 °C

2: 95 percent / Et₃N / CH₂Cl₂ / 12 h

3: 89 percent / pyridine / 0 °C

4: 52 percent / NaN₃, Bu₄NHSO₄ / dimethylformamide / 36 h / 80 °C

With pyridine; sodium azide; tetra(n-butyl)ammonium hydrogensulfate; hydrazine hydrate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/07328309608005660

upstream raw materials:

benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside

benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside

benzyl 4,6-O-benzylidene-2-deoxy-2-trifluoroacetamido-α-D-glucopyranoside

Downstream raw materials:

N-((2S,3R,4R,5S,6R)-4-Azido-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-3-yl)-2,2,2-trifluoro-acetamide

N-[(2S,3R,4R,5S,6R)-4-Azido-2-benzyloxy-6-benzyloxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide