(20S,24R)-20,24-Epoxydammarane-3α,12β,25-triol

Base Information

• Chemical Name: (20S,24R)-20,24-Epoxydammarane-3α,12β,25-triol
• CAS No.: 19942-05-3
• Molecular Formula: C30H52O4
• Molecular Weight: 476.73
• Mol file: 19942-05-3.mol

Synonyms:betulafolienetriol oxide;(24R)-20,24-epoxydammarane-3α,12β,25-triol;betulatriterpene C;(3R,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S,5R)-5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,12-diol;3α,12β,25-trihydroxy-20S,24R-epoxydammarane;

Chemical Property of (20S,24R)-20,24-Epoxydammarane-3α,12β,25-triol

Chemical Property:

• PSA: 69.92000
• LogP: 5.71180

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (20S,24R)-20,24-Epoxydammarane-3α,12β,25-triol

There total 12 articles about (20S,24R)-20,24-Epoxydammarane-3α,12β,25-triol 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: 84.0%

3-O-malonyl-12β-acetoxy-3α,25-dihydroxy-(20S,24R)-epoxydammarane (78782-15-7) → betulafolienetriol oxide (19942-05-3)

Guidance literature:

With potassium hydroxide; In ethanol; for 1h; Heating;

DOI:10.1021/jo00335a054

Reference yield: 72.0%

(8R,10R,14R)-17-[(2S,5R)-5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,8,10,14-pentamethyl-tetradecahydro-cyclopenta[a]phenanthrene-3,12-dione (19942-06-4,25279-16-7,33770-12-6,67253-02-5) → 20(S),24(R)-Epoxydammarane-3β,12α,25-triol (19667-15-3,19942-05-3,19942-07-5,25330-18-1,87480-27-1,88195-75-9,141979-08-0)

Guidance literature:

With LiAlH(OC₄H₉)3; In tetrahydrofuran; for 7h; Heating;

DOI:10.1007/BF00580552

Reference yield: 27.0%

Cholesteryl (α-D-glucose orthoacetate) (3254-14-6,58769-34-9,128385-59-1) + Betulafolienetriol oxide (19667-15-3,19942-05-3,19942-07-5,25330-18-1,87480-27-1,88195-75-9,141979-08-0) → Z-12β-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-3α-hydroxydammar-20(22)-en-24-one (88109-93-7,88109-94-8) + (3R,8R,10R,12R,14R)-17-[(R)-5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,12-diol (19667-15-3,19942-05-3,19942-07-5,25330-18-1,87480-27-1,88195-75-9,141979-08-0)

Guidance literature:

With mercury dibromide; In nitromethane; at 100 - 105 ℃; for 0.666667h;

DOI:10.1007/BF00579764

upstream raw materials:

3-O-malonylbetulafolientriol I

12β,25-Dihydroxy-20(S),24(R)-epoxydammaran-3-one

Betulafolienetriol oxide

Cholesteryl (α-D-glucose orthoacetate)

Downstream raw materials:

20(S),24(R)-Epoxydammarane-3β,12β,25-triol

Z-12β-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-3α-hydroxydammar-20(22)-en-24-one

(3R,8R,10R,12R,14R)-17-[(R)-5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,12-diol

(20S,24R)-epoxydammarane–12β,25-diol-3-one

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