(17a)-17-(Acetyloxy)-19-norpregna-1,3,5(10)-trien-20-yn-3-yl--D-Glucopyranosiduronic Acid Methyl Ester Triacetate

Base Information

• Chemical Name: (17a)-17-(Acetyloxy)-19-norpregna-1,3,5(10)-trien-20-yn-3-yl--D-Glucopyranosiduronic Acid Methyl Ester Triacetate
• CAS No.: 242130-33-2
• Molecular Formula: C₃₅H₄₂O₁₂
• Molecular Weight: 654.711
• Mol file: 242130-33-2.mol

Synonyms:(17a)-17-(Acetyloxy)-19-norpregna-1,3,5(10)-trien-20-yn-3-yl--D-Glucopyranosiduronic Acid Methyl Ester Triacetate;Ethynylestradiol 17-Acetate 3-(2’, 3’,4’-Tri-O-acetyl)--D-glucuronide Methyl Ester

Chemical Property of (17a)-17-(Acetyloxy)-19-norpregna-1,3,5(10)-trien-20-yn-3-yl--D-Glucopyranosiduronic Acid Methyl Ester Triacetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.565
• Boiling Point: 673.571°C at 760 mmHg
• Flash Point: 275.764°C
• PSA: 149.96000
• Density: 1.305g/cm³
• LogP: 3.54960
• Solubility.: Chloroform

Purity/Quality:

97% ^*data from raw suppliers

EthynylEstradiol17-Acetate3-(2’,3’,4’-Tri-O-acetyl)-β-D-glucuronideMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate for the preparation of Ethynylestradiol 3--D-Glucuronid Intermediate for the preparation of Ethynylestradiol 3-β-D-Glucuronid.

Technology Process of (17a)-17-(Acetyloxy)-19-norpregna-1,3,5(10)-trien-20-yn-3-yl--D-Glucopyranosiduronic Acid Methyl Ester Triacetate

There total 3 articles about (17a)-17-(Acetyloxy)-19-norpregna-1,3,5(10)-trien-20-yn-3-yl--D-Glucopyranosiduronic Acid Methyl Ester Triacetate 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: 61.0%

17β-acetoxy-17α-ethynyl-3-hydroxy-1,3,5[10]-estratriene (21221-29-4) + methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) → methyl {(17β-acetoxy-17α-ethynyl-1,3,5[10]-estratrien-3-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate (242130-33-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 0.5h;

DOI:10.1080/07328309908544025

Reference yield:

ethynylestradiol diacetate (13258-68-9) → methyl {(17β-acetoxy-17α-ethynyl-1,3,5[10]-estratrien-3-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate (242130-33-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / potassium carbonate / methanol / 0.5 h / 20 °C

2: 61 percent / boron trifluoride diethyl etherate / CH₂Cl₂ / 0.5 h / -20 °C

With boron trifluoride diethyl etherate; potassium carbonate; In methanol; dichloromethane; 1: Deacetylation / 2: glucuronidation;

DOI:10.1080/07328309908544025

Reference yield:

ethinyl estradiol (57-63-6) → methyl {(17β-acetoxy-17α-ethynyl-1,3,5[10]-estratrien-3-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate (242130-33-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / pyridine / 48 h / 100 °C

2: 66 percent / potassium carbonate / methanol / 0.5 h / 20 °C

3: 61 percent / boron trifluoride diethyl etherate / CH₂Cl₂ / 0.5 h / -20 °C

With pyridine; boron trifluoride diethyl etherate; potassium carbonate; In methanol; dichloromethane; 1: Acetylation / 2: Deacetylation / 3: glucuronidation;

DOI:10.1080/07328309908544025

upstream raw materials:

17β-acetoxy-17α-ethynyl-3-hydroxy-1,3,5[10]-estratriene

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate

ethynylestradiol diacetate

ethinyl estradiol

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