17β-hydroxy Wortmannin

Base Information

• Chemical Name: 17β-hydroxy Wortmannin
• CAS No.: 58053-83-1
• Molecular Formula: C23H26O8
• Molecular Weight: 430.455
• Mol file: 58053-83-1.mol

Synonyms:17-dihydrowortmannin;17-hydroxy-wortmannin;17-OH wortmannin;

Chemical Property of 17β-hydroxy Wortmannin

Chemical Property:

• Boiling Point: 615.4±55.0 °C(Predicted)
• PKA: 14.49±0.70(Predicted)
• PSA: 112.27000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 2.32820
• Storage Temp.: +2C to +8C

Purity/Quality:

99% ^*data from raw suppliers

PI 3-K Inhibitor XI, HWT - CAS 58053-83-1 - Calbiochem ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 17β-hydroxy Wortmannin is an analog of wortmannin. It irreversibly binds phosphoinositide 3-kinase (PI3K) and potently blocks fMLP-stimulated respiratory burst in neutrophils (IC50 = 5 nM). 17β-hydroxy Wortmannin inhibits recombinant PI3K and mTOR (IC50 = 2.7 and 193 nM, respectively) and prevents the growth of LNCap prostate cancer cells (IC50 = 1.46 μM). The 17-hydroxyl group has been used to further modify this compound, e.g., by pegylation and conjugation with rapamycin.

Technology Process of 17β-hydroxy Wortmannin

There total 49 articles about 17β-hydroxy Wortmannin 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: 89.0%

wortmannin (19545-26-7) → 17-beta-Hydroxywortmannin (58053-83-1,108740-89-2)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 0 ℃; for 3.5h;

Reference yield: 76.0%

C27H38O7Si + acetic anhydride (108-24-7) → 17-beta-Hydroxywortmannin (58053-83-1,108740-89-2)

Guidance literature:

C₂₇H₃₈O₇Si; acetic anhydride; In pyridine; at 20 ℃; for 12h;

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 45 ℃; for 12h;

DOI:10.1021/jacs.7b02515

Reference yield: 49.0%

acetic anhydride (108-24-7) + (3S,3aS,5R,5bR,6S,11bR)-3,5-Dihydroxy-6-methoxymethyl-3a,5b-dimethyl-2,3,3a,4,5,5b,6,11b-octahydro-1H-7,10-dioxa-cyclopenta[j]acephenanthrylene-8,11-dione (182203-32-3) → 17-beta-Hydroxywortmannin (58053-83-1,108740-89-2)

Guidance literature:

With pyridine; at -20 ℃; for 12h;

DOI:10.1016/0040-4039(96)01332-9

upstream raw materials:

wortmannin

acetic anhydride

(3S,3aS,5R,5bR,6S,11bR)-3,5-Dihydroxy-6-methoxymethyl-3a,5b-dimethyl-2,3,3a,4,5,5b,6,11b-octahydro-1H-7,10-dioxa-cyclopenta[j]acephenanthrylene-8,11-dione

9α,11α-epoxy-4-androstene-3,17-dione

Downstream raw materials:

wortmannin