3,17beta-Di(tetrahydropyranyloxy)-6-keto-estra-1,3,5(10)-triene

Base Information

• Chemical Name: 3,17beta-Di(tetrahydropyranyloxy)-6-keto-estra-1,3,5(10)-triene
• CAS No.: 53573-82-3
• Molecular Formula: C28H38O5
• Molecular Weight: 454.607
• DSSTox Substance ID: DTXSID40471275
• Nikkaji Number: J1.690.889D
• Mol file: 53573-82-3.mol

Synonyms:53573-82-3;3,17beta-di(tetrahydropyranyloxy)-6-keto-estra-1,3,5(10)-triene;(8R,9S,13S,14S,17S)-13-methyl-3,17-bis(oxan-2-yloxy)-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-6-one;Estra-1,3,5(10)-trien-6-one, 3,17-bis[(tetrahydro-2H-pyran-2-yl)oxy]-, (17|A)-;Estra-1,3,5(10)-trien-6-one, 3,17-bis[(tetrahydro-2H-pyran-2-yl)oxy]-, (17;TZVFNUBGWDFYRL-XIOQBIFOSA-N;SCHEMBL3645385;DTXSID40471275;(17|A)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-one;(17beta)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-one;A933622;Estra-1,3,5(10)-trien-6-one, 3,17-bis[(tetrahydro-2H-pyran-2-yl)oxy]-, (17)-;A)-

Chemical Property of 3,17beta-Di(tetrahydropyranyloxy)-6-keto-estra-1,3,5(10)-triene

Chemical Property:

• Boiling Point: 597.3±50.0 °C(Predicted)
• PSA: 53.99000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 6.00010
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 454.27192431
• Heavy Atom Count: 33
• Complexity: 710

Purity/Quality:

98.5% ^*data from raw suppliers

(17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2OC4CCCCO4)CC(=O)C5=C3C=CC(=C5)OC6CCCCO6
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC4CCCCO4)CC(=O)C5=C3C=CC(=C5)OC6CCCCO6
• Uses: (17β)-3,17-Bis[(tetrahydro-2H-pyran-2-yl)oxy]-estra-1,3,5(10)-trien-6-one is 17β-Estradiol (E888000) derivative. Used in the preparation of antiestrogenic steroids.

Technology Process of 3,17beta-Di(tetrahydropyranyloxy)-6-keto-estra-1,3,5(10)-triene

There total 7 articles about 3,17beta-Di(tetrahydropyranyloxy)-6-keto-estra-1,3,5(10)-triene 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: 99.0%

3,4-dihydro-2H-pyran (110-87-2) + ent-3,17β-dihydroxyestra-1,3,5(10)-trien-6-one → 3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene-6-one (53573-82-3)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃;

Reference yield: 95.0%

(8R,9S,13S,14S,17S)-13-Methyl-3,17-bis-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-ol (122566-22-7) → 3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene-6-one (53573-82-3)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

Reference yield:

3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene (3589-91-1) → 3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene-6-one (53573-82-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi; diisopropylamine; t-BuOK / 3 h / -78 °C

1.2: B(OMe)3 / 2 h / 0 °C

1.3: H₂O₂ / 1 h / 20 °C

2.1: pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 1 h / 20 °C

With n-butyllithium; potassium tert-butylate; sodium acetate; diisopropylamine; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/j.bmc.2006.10.055

upstream raw materials:

(8R,9S,13S,14S,17S)-13-Methyl-3,17-bis-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-ol

3,4-dihydro-2H-pyran

6-ketoestradiol

3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene

Downstream raw materials:

6-ketoestradiol

N-butyl-N-methyl-7-(3-benzyloxy-17-oxoestra-1,3,5(10)-trien-6β-yl)heptanamide

N-butyl-N-methyl-7-(3-benzyloxy-17β-hydroxy-2-methoxyestra-1,3,5(10)-trien-6β-yl)heptanamide

N-butyl-N-methyl-7-(3-benzyloxy-2-methoxy-17-oxoestra-1,3,5(10)-trien-6β-yl)heptanamide