(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((2R,5R,6S)-5,6,7-trihydroxy-6-methylheptan-2-yl)-4,5,6,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

Base Information

• Chemical Name: (5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((2R,5R,6S)-5,6,7-trihydroxy-6-methylheptan-2-yl)-4,5,6,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
• CAS No.: 1345457-33-1
• Molecular Formula: C₃₀H₄₈O₄
• Molecular Weight: 472.709
• Mol file: 1345457-33-1.mol

Synonyms:

Chemical Property of (5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((2R,5R,6S)-5,6,7-trihydroxy-6-methylheptan-2-yl)-4,5,6,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((2R,5R,6S)-5,6,7-trihydroxy-6-methylheptan-2-yl)-4,5,6,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

There total 8 articles about (5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((2R,5R,6S)-5,6,7-trihydroxy-6-methylheptan-2-yl)-4,5,6,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-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: 56.0%

(5R,10S,13R,14R,17R)-17-((R,Z)-7-hydroxy-6-methylhept-5-en-2-yl)-4,4,10,13,14-pentamethyl-4,5,6,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one (1345457-30-8) → (5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((2R,5R,6S)-5,6,7-trihydroxy-6-methylheptan-2-yl)-4,5,6,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one (1345457-33-1,106518-63-2)

Guidance literature:

With methanesulfonamide; AD-Mix β; water; In tert-butyl alcohol; at 25 ℃; for 6h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/np200205n

Reference yield:

(4R)-4-((5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3-oxo-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanal (1345457-17-1) → (5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((2R,5R,6S)-5,6,7-trihydroxy-6-methylheptan-2-yl)-4,5,6,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one (1345457-33-1,106518-63-2)

Guidance literature:

Multi-step reaction with 7 steps

1: lithium bromide / tetrahydrofuran / Inert atmosphere

2: 3-chloro-benzenecarboperoxoic acid / chloroform / 12 h / 25 °C / Inert atmosphere

3: toluene-4-sulfonic acid / toluene / 1 h / 60 °C / Inert atmosphere

4: toluene-4-sulfonic acid / benzene / 20 h / Inert atmosphere; Reflux

5: diisobutylaluminium hydride / hexane; dichloromethane / 0.87 h / -100 °C / Inert atmosphere

6: toluene-4-sulfonic acid / acetone / 24 h / Inert atmosphere; Reflux

7: AD-Mix β; methanesulfonamide; water / tert-butyl alcohol / 6 h / 25 °C / Inert atmosphere

With methanesulfonamide; AD-Mix β; water; diisobutylaluminium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; hexane; dichloromethane; chloroform; acetone; toluene; tert-butyl alcohol; benzene; 1: Horner-Wadsworth-Emmons olefination / 7: Sharpless dihydroxylation;

DOI:10.1021/np200205n

Reference yield:

tirucallol (79-63-0) → (5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((2R,5R,6S)-5,6,7-trihydroxy-6-methylheptan-2-yl)-4,5,6,10,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one (1345457-33-1,106518-63-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.03 h / -60 - -20 °C / Inert atmosphere

1.2: -20 - 25 °C / Inert atmosphere

1.3: 0.28 h / -50 °C / Inert atmosphere

2.1: lithium bromide / tetrahydrofuran / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 12 h / 25 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / toluene / 1 h / 60 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / benzene / 20 h / Inert atmosphere; Reflux

6.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.87 h / -100 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / acetone / 24 h / Inert atmosphere; Reflux

8.1: AD-Mix β; methanesulfonamide; water / tert-butyl alcohol / 6 h / 25 °C / Inert atmosphere

With oxalyl dichloride; methanesulfonamide; AD-Mix β; water; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; hexane; dichloromethane; chloroform; acetone; toluene; tert-butyl alcohol; benzene; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Horner-Wadsworth-Emmons olefination / 8.1: Sharpless dihydroxylation;

DOI:10.1021/np200205n

upstream raw materials:

ethyl (6R,Z)-2-methyl-6-((5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3-oxo-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)hept-2-enoate

ethyl (6R,Z)-2-methyl-6-((5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3-oxotetradecahydro-1H-8,9-epoxycyclopenta[a]phenanthren-17-yl)hept-2-enoate

ethyl (6R,Z)-2-methyl-6-((5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3-oxo-2,3,4,5,6,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)hept-2-enoate

ethyl (6R,Z)-2-methyl-6-((5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-1,2,4,5,6,10,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-yl)hept-2-enoate