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

Base Information

• Chemical Name: 2-((2R,4aR,6R,7R,8S,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione
• CAS No.: 224309-08-4
• Molecular Formula: C₂₈H₂₄N₄O₆
• Molecular Weight: 512.522
• Mol file: 224309-08-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

Trifluoro-methanesulfonic acid (2R,4aR,6R,7R,8R,8aR)-6-benzyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester → 2-((2R,4aR,6R,7R,8S,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (224309-08-4)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 75 ℃; Yield given;

DOI:10.1016/S0960-894X(99)00154-7

Reference yield: 79.0%

2-((2R,4aR,6R,7R,8S,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (224309-08-4) → 2-((2R,3R,4S,5S,6R)-4-Azido-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (224309-10-8)

Guidance literature:

With acetic acid; at 70 ℃;

DOI:10.1016/S0960-894X(99)00154-7

Reference yield:

2-((2R,4aR,6R,7R,8S,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (224309-08-4) → Diaminopyranoside

Guidance literature:

Multi-step reaction with 9 steps

1: 79 percent / aq. AcOH / 70 °C

2: 87 percent / imidazole / dimethylformamide / Ambient temperature

3: 68 percent / NaH / dimethylformamide / 0 °C

4: 98 percent / aq. AcOH / tetrahydrofuran / Ambient temperature

5: hydrazine monohydrate / ethanol / 90 °C

6: ethanol / Ambient temperature

7: Ph₃P / tetrahydrofuran / Heating

8: tetrahydrofuran; H₂O / 50 °C

9: 94 percent / aq. HCl / dioxane; ethanol / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium hydride; hydrazine hydrate; acetic acid; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(99)00154-7

Downstream raw materials:

2-((2R,3R,4S,5S,6R)-4-Azido-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

((2R,3S,4S,5R,6R)-5-Amino-4-azido-3,6-bis-benzyloxy-tetrahydro-pyran-2-yl)-methanol

((2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

2-((2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione