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

Base Information

• Chemical Name: N-Allyl-N-((2R,4aR,6S,7R,8S,8aS)-7-allyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-2,2,2-trifluoro-acetamide
• CAS No.: 851190-94-8
• Molecular Formula: C₂₂H₂₆F₃NO₅
• Molecular Weight: 441.447
• Mol file: 851190-94-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about N-Allyl-N-((2R,4aR,6S,7R,8S,8aS)-7-allyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-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: 76.0%

trifluoroacetic anhydride (407-25-0) + Allyl-((2R,4aR,6S,7R,8S,8aS)-7-allyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-amine (851190-93-7) → N-Allyl-N-((2R,4aR,6S,7R,8S,8aS)-7-allyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-2,2,2-trifluoro-acetamide (851190-94-8)

Guidance literature:

di-isopropylphosphine; With n-butyllithium; In tetrahydrofuran; at -70 - 20 ℃;

ethyleneglycol sulfate; In tetrahydrofuran; at -70 - 20 ℃;

lithium diphenylphosphide; In tetrahydrofuran; at -70 - 60 ℃;

DOI:10.1039/b401585a

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose (138750-12-6) → N-Allyl-N-((2R,4aR,6S,7R,8S,8aS)-7-allyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-2,2,2-trifluoro-acetamide (851190-94-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: AcOH / tetrahydrofuran

1.2: 76 percent / NaCNBH₃ / tetrahydrofuran / 2 h / 20 °C

2.1: 85 percent / pyridine / CH₂Cl₂ / 16 h / 20 °C

With pyridine; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2005.02.007

Reference yield: 65.0%

N-Allyl-N-((2R,4aR,6S,7R,8S,8aS)-7-allyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-2,2,2-trifluoro-acetamide (851190-94-8) → 2,2,2-Trifluoro-1-((2R,4aR,6S,6aR,11aS,11bS)-6-methoxy-2-phenyl-4,4a,6,6a,7,10,11a,11b-octahydro-1,3,5-trioxa-11-aza-cyclohepta[a]naphthalen-11-yl)-ethanone (851190-95-9)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 16h; Heating;

DOI:10.1016/j.tetlet.2005.02.007

upstream raw materials:

trifluoroacetic anhydride

Allyl-((2R,4aR,6S,7R,8S,8aS)-7-allyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-amine

methyl 4,6-O-benzylidene-2-deoxy-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose

Downstream raw materials:

2,2,2-Trifluoro-1-((2R,4aR,6S,6aR,11aS,11bS)-6-methoxy-2-phenyl-4,4a,6,6a,7,10,11a,11b-octahydro-1,3,5-trioxa-11-aza-cyclohepta[a]naphthalen-11-yl)-ethanone