(2-methyl-3-phenylchromonyl-7)-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: (2-methyl-3-phenylchromonyl-7)-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 388582-43-2
• Molecular Formula: C₃₀H₃₁NO₁₁
• Molecular Weight: 581.576
• Mol file: 388582-43-2.mol

Synonyms:(2-methyl-3-phenylchromonyl-7)-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Chemical Property of (2-methyl-3-phenylchromonyl-7)-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-methyl-3-phenylchromonyl-7)-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

There total 1 articles about (2-methyl-3-phenylchromonyl-7)-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 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: 66.0%

7-hydroxy-2-methyl-3-phenyl-chromen-4-one (2859-88-3) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → (2-methyl-3-phenylchromonyl-7)-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (388582-43-2)

Guidance literature:

With 15-crown-5; potassium carbonate; In acetonitrile; at 20 ℃;

DOI:10.1023/A:1017694224906 DOI:10.1023/A:1019635914082

Reference yield: 86.0%

(2-methyl-3-phenylchromonyl-7)-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (388582-43-2) → (2-methyl-3-phenylchromonyl-7)-2-acetamido-2-deoxy-β-D-glucopyranoside (388582-46-5)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1023/A:1017694224906

Reference yield:

(2-methyl-3-phenylchromonyl-7)-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (388582-43-2) → (R)-4-((S)-2-{(R)-2-[(2S,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-(2-methyl-4-oxo-3-phenyl-4H-chromen-7-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid methyl ester

Guidance literature:

Multi-step reaction with 5 steps

1.1: 86 percent / MeONa / methanol

2.1: 62 percent / TsOH / tetrahydrofuran / 1 h / Heating

3.1: 93 percent / NaH / dioxane / 3 h / 65 °C

4.1: N-hydroxysuccinimide; dicyclohexylcarbodiimide / dioxane / 3 h

4.2: 66 percent / Et₃N / dioxane

5.1: 51 percent / aq. acetic acid / 0.08 h / Heating

With 1-hydroxy-pyrrolidine-2,5-dione; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1023/A:1017694224906

upstream raw materials:

7-hydroxy-2-methyl-3-phenyl-chromen-4-one

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

Downstream raw materials:

(2-methyl-3-phenylchromonyl-7)-2-acetamido-2-deoxy-β-D-glucopyranoside

(2-methyl-3-phenylchromonyl-7)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

(R)-2-[(4aR,6S,7R,8R,8aS)-7-Acetylamino-2,2-dimethyl-6-(2-methyl-4-oxo-3-phenyl-4H-chromen-7-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionic acid