2,3,14,20,22,25-hexahydroxy-26-(3-bromoacetoxypropyl)cholest-7-en-6-one

Base Information

• Chemical Name: 2,3,14,20,22,25-hexahydroxy-26-(3-bromoacetoxypropyl)cholest-7-en-6-one
• CAS No.: 123171-56-2
• Molecular Formula: C₃₂H₅₁BrO₉
• Molecular Weight: 659.656
• Mol file: 123171-56-2.mol

Synonyms:2,3,14,20,22,25-hexahydroxy-26-(3-bromoacetoxypropyl)cholest-7-en-6-one

Chemical Property of 2,3,14,20,22,25-hexahydroxy-26-(3-bromoacetoxypropyl)cholest-7-en-6-one

Chemical Property:

• Vapor Pressure: 4.12E-30mmHg at 25°C
• Boiling Point: 806.6°Cat760mmHg
• PKA: 14.13±0.70(Predicted)
• Flash Point: 441.6°C
• PSA: 164.75000
• Density: 1.39g/cm³
• LogP: 2.94250

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3,14,20,22,25-hexahydroxy-26-(3-bromoacetoxypropyl)cholest-7-en-6-one

There total 7 articles about 2,3,14,20,22,25-hexahydroxy-26-(3-bromoacetoxypropyl)cholest-7-en-6-one 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: 64.0%

bromoacetic acid (79-08-3) + C46H68O8Si → Bromo-acetic acid (5S,8R,9R)-5,8,9-trihydroxy-5-methyl-9-((2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-decyl ester (123171-56-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; at -20 ℃; for 3h;

Reference yield:

tert-Butyl-[4-((S)-2-methyl-2,3-dihydro-furan-2-yl)-butoxy]-diphenyl-silane (123171-35-7) → Bromo-acetic acid (5S,8R,9R)-5,8,9-trihydroxy-5-methyl-9-((2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-decyl ester (123171-56-2)

Guidance literature:

Multi-step reaction with 4 steps

1: tBuLi / tetrahydrofuran / 2 h / -78 - -20 °C

2: 0.1 N HCl / tetrahydrofuran; H₂O / 0.5 h / 20 °C

4: 64 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / tetrahydrofuran / 3 h / -20 °C

With hydrogenchloride; dmap; tert.-butyl lithium; dicyclohexyl-carbodiimide; In tetrahydrofuran; water;

Reference yield:

6-(tert-butyldiphenylsilyloxy)hexan-2-one (123171-29-9) → Bromo-acetic acid (5S,8R,9R)-5,8,9-trihydroxy-5-methyl-9-((2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-decyl ester (123171-56-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 77 percent / tetrahydrofuran / 2 h / Heating

2: 89 percent / Rh(PPh₃)3(CO)Cl, NEt₃, H₂ / benzene / 37503 Torr

3: Al₂O₃, SiO₂ / 270 °C / 0.1 Torr

4: tBuLi / tetrahydrofuran / 2 h / -78 - -20 °C

5: 0.1 N HCl / tetrahydrofuran; H₂O / 0.5 h / 20 °C

7: 64 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / tetrahydrofuran / 3 h / -20 °C

With hydrogenchloride; dmap; aluminum oxide; carbonylchlorohydridotris(triphenylphosphine)ruthenium(II); hydrogen; tert.-butyl lithium; silica gel; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; benzene;

upstream raw materials:

bromoacetic acid

(20R,25S)-27(3-(tert-butyl-diphenyl-silanyloxy)-propyl)-2β,3β,14,20,25,5β-pentahydroxycholest-7-ene-6,22-dione

tert-Butyl-[4-((S)-2-methyl-2,3-dihydro-furan-2-yl)-butoxy]-diphenyl-silane

6-(tert-butyldiphenylsilyloxy)hexan-2-one