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

Base Information

• Chemical Name: Allyl-((2R,4aR,6S,7R,8S,8aS)-7-allyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-amine
• CAS No.: 851190-93-7
• Molecular Formula: C₂₀H₂₇NO₄
• Molecular Weight: 345.439
• Mol file: 851190-93-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

methyl 4,6-O-benzylidene-2-deoxy-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose (138750-12-6) + 1-amino-2-propene (107-11-9,30551-89-4) → 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)

Guidance literature:

methyl 4,6-O-benzylidene-2-deoxy-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose; 1-amino-2-propene; With acetic acid; In tetrahydrofuran;

With sodium cyanoborohydride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2005.02.007

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:

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) → (2R,4aR,6S,6aR,11aS,11bS)-6-Methoxy-2-phenyl-4a,6,6a,7,10,11,11a,11b-octahydro-4H-1,3,5-trioxa-11-aza-cyclohepta[a]naphthalene

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / pyridine / CH₂Cl₂ / 16 h / 20 °C

2: 65 percent / Grubb's catalyst / CH₂Cl₂ / 16 h / Heating

3: 84 percent / NaBH₄ / ethanol / 24 h / Heating

With pyridine; sodium tetrahydroborate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In ethanol; dichloromethane;

DOI:10.1016/j.tetlet.2005.02.007

upstream raw materials:

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

1-amino-2-propene

Downstream raw materials:

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

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