21-Acetoxy-11β-hydroxy-16α,17α-propylmethylenedioxpregna-1,4-diene-3,20-dione

Base Information

• Chemical Name: 21-Acetoxy-11β-hydroxy-16α,17α-propylmethylenedioxpregna-1,4-diene-3,20-dione
• CAS No.: 51333-05-2
• Molecular Formula: C₂₇H₃₆O₇
• Molecular Weight: 472.579
• Mol file: 51333-05-2.mol

Synonyms:21-Acetoxy-11β-hydroxy-16α,17α-propylmethylenedioxpregna-1,4-diene-3,20-dione;(11β,16α)-21-(Acetyloxy)-16,17-[butylidenebis(oxy)]-11-hydroxy-pregna-1,4-diene-3,20-dione;21-(Acetoxy)-16α,17α-(butylidenedioxy)-11β-hydroxypregna-1,4diene-3,20-dione-d8;21-Acetyloxy Budesonide-d8

Chemical Property of 21-Acetoxy-11β-hydroxy-16α,17α-propylmethylenedioxpregna-1,4-diene-3,20-dione

Chemical Property:

• Boiling Point: 611.4±55.0 °C(Predicted)
• PKA: 14.26±0.70(Predicted)
• PSA: 99.13000
• Density: 1.26±0.1 g/cm3(Predicted)
• LogP: 3.28760
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

21-Acetyloxy Budesonide-d8 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Protected Budesonide-d8 (B689492), 21-Acetoxy-11β-hydroxy-16α,17α-propylmethylenedioxpregna-1,4-diene-3,20-dione is a non-halogenated glucocorticoid related to triamcinolone hexacetonide. Used as an antiinflammatory agent. 21-Acetoxy-11β-hydroxy-16α,17α-propylmethylenedioxpregna-1,4-diene-3,20-dione (Budesonide EP Impurity K) is an impurity of Budesonide (B689460), a non-halogenated glucocorticoid intended for the local treatment of lung disease.

Technology Process of 21-Acetoxy-11β-hydroxy-16α,17α-propylmethylenedioxpregna-1,4-diene-3,20-dione

There total 7 articles about 21-Acetoxy-11β-hydroxy-16α,17α-propylmethylenedioxpregna-1,4-diene-3,20-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: 98.0%

C27H34O7 → 2-((6aR,6bS,7S,8aS,8bS,11aR,12aS,12bS)-7-hydroxy-6a,8a-dimethyl-4-oxo-10-propyl-2,4,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-8b-yl)-2-oxoethyl acetate (51333-05-2)

Guidance literature:

With methanol; sodium tetrahydroborate; at 0 - 5 ℃; Reagent/catalyst;

Reference yield: 64.8%

11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate (86401-80-1) + butyraldehyde (123-72-8) → (R)-budesonide acetate (51333-05-2)

Guidance literature:

In perchloric acid; at -20 ℃; for 3h; Inert atmosphere;

Reference yield:

11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate (86401-80-1) + butyraldehyde (123-72-8) → 2-((6aR,6bS,7S,8aS,8bS,11aR,12aS,12bS)-7-hydroxy-6a,8a-dimethyl-4-oxo-10-propyl-2,4,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-8b-yl)-2-oxoethyl acetate (51333-05-2)

Guidance literature:

With perchloric acid; In ethyl acetate; at 45 ℃; for 2h; Solvent; Temperature; Inert atmosphere;

upstream raw materials:

budesonide

acetic anhydride

11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate

butyraldehyde

Downstream raw materials:

(22R)-21-acetoxy-6α,11β-dihydroxy-16α,17α-propylmethylenedioxypregna-1,4-diene-3,20-dione

(22R)-21-acetoxy-6β,11β-dihydroxy-16α,17α-propylmethylenedioxypregna-1,4-diene-3,20-dione

Refernces

• 1、 -. "A preparation method of budesonide". . . Retrieved 2017/08/25.
• 2、 -. "PHOSPHATE BASED LINKERS FOR INTRACELLULAR DELIVERY OF DRUG CONJUGATES". Page/Page column 73. . Retrieved 2015/11/18.