(4aR,6R,7R,8S,8aS)-8-Azido-6,7-dimethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (4aR,6R,7R,8S,8aS)-8-Azido-6,7-dimethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 601489-20-7
• Molecular Formula: C₁₆H₂₁N₃O₆
• Molecular Weight: 351.359
• Mol file: 601489-20-7.mol

Synonyms:(4aR,6R,7R,8S,8aS)-8-Azido-6,7-dimethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property of (4aR,6R,7R,8S,8aS)-8-Azido-6,7-dimethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6R,7R,8S,8aS)-8-Azido-6,7-dimethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 5 articles about (4aR,6R,7R,8S,8aS)-8-Azido-6,7-dimethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 95.0%

(4aR,6R,7R,8R,8aS)-8-Azido-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (601489-15-0) + methyl iodide (74-88-4) → (4aR,6R,7R,8S,8aS)-8-Azido-6,7-dimethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (601489-20-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 1h;

DOI:10.1016/S0960-894X(03)00384-6

Reference yield:

methyl 3-azido-3-deoxy-β-D-glucopyranoside (65784-76-1) → (4aR,6R,7R,8S,8aS)-8-Azido-6,7-dimethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (601489-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 4 h

2: 95 percent / NaH / dimethylformamide / 1 h

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00384-6

Reference yield:

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose (185114-94-7,155417-78-0) → (4aR,6R,7R,8S,8aS)-8-Azido-6,7-dimethoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (601489-20-7)

Guidance literature:

Multi-step reaction with 5 steps

1: Me₃SiBr; BiBr₃ / CH₂Cl₂ / 4 h

2: Ag₂O; CaSO₄ / CH₂Cl₂ / 1 h

3: MeONa; MeOH / 4 h

4: 68 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 4 h

5: 95 percent / NaH / dimethylformamide / 1 h

With methanol; calcium sulfate; bismuth(III) bromide; trimethylsilyl bromide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00384-6

upstream raw materials:

(4aR,6R,7R,8R,8aS)-8-Azido-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

methyl iodide

methyl 3-azido-3-deoxy-β-D-glucopyranoside

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

Downstream raw materials:

(2R,3S,4S,5R,6R)-4-Azido-5,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

[(2R,3S,4S,5R,6R)-4-Azido-5,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yloxy]-acetic acid methyl ester