(3S,5R,8R,9R,10R,14R)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

Base Information

• Chemical Name: (3S,5R,8R,9R,10R,14R)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS No.: 14351-29-2
• Molecular Formula: C₃₀H₅₂O₂
• Molecular Weight: 444.742
• DSSTox Substance ID: DTXSID50931936
• Wikidata: Q105181348
• Mol file: 14351-29-2.mol

Synonyms:3beta-dammar-24-ene-3,20-diol;dammarenediol;dammarenediol II

Chemical Property of (3S,5R,8R,9R,10R,14R)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

Chemical Property:

• Vapor Pressure: 2.02E-13mmHg at 25°C
• Melting Point: 130-133 °C
• Refractive Index: 1.517
• Boiling Point: 529.4 °C at 760 mmHg
• PKA: 15.06±0.29(Predicted)
• Flash Point: 212 °C
• PSA: 40.46000
• Density: 0.993 g/cm³
• LogP: 7.52980
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 444.396730897
• Heavy Atom Count: 32
• Complexity: 750

Purity/Quality:

99% ^*data from raw suppliers

DammarenediolII 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(C)(C1CCC2(C1CCC3C2(CCC4C3(CCC(C4(C)C)O)C)C)C)O)C
• Isomeric SMILES: CC(=CCC[C@@](C)(C1CC[C@@]2(C1CC[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C)O)C
• General Description: Dammarenediol is a triterpenoid compound with two known stereoisomers, dammarenediol-I and dammarenediol-II, which differ in the absolute configuration at C(20). Dammarenediol-I has an R configuration at C(20), while dammarenediol-II has an S configuration at the same position. These compounds are structurally related to protopanaxadiol, a sapogenin found in Ginseng saponins. The stereochemical distinction at C(20) is significant for understanding their biological activity and biosynthesis.

Technology Process of (3S,5R,8R,9R,10R,14R)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

There total 84 articles about (3S,5R,8R,9R,10R,14R)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol 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: 100.0%

(R)-2-[(3S,5R,9S,10R,13S,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-6-methyl-hept-5-en-2-ol (128685-91-6,128777-75-3,136734-43-5,136735-34-7) → (3S,5R,9S,10R,13S,14S,17R)-17-((R)-1-Hydroxy-1,5-dimethyl-hex-4-enyl)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol (14351-28-1,14351-29-2,19132-83-3,33426-07-2,53368-74-4,59686-24-7,111956-30-0,114926-01-1,128777-74-2,136734-44-6,136734-47-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 10h;

Reference yield: 100.0%

(S)-2-[(3S,5R,9S,10R,13S,14S,17R)-3-(tert-Butyl-dimethyl-silanyloxy)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-6-methyl-hept-5-en-2-ol (128685-91-6,128777-75-3,136734-43-5,136735-34-7) → (3S,5R,9S,10R,13S,14S,17R)-17-((S)-1-Hydroxy-1,5-dimethyl-hex-4-enyl)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol (14351-28-1,14351-29-2,19132-83-3,33426-07-2,53368-74-4,59686-24-7,111956-30-0,114926-01-1,128777-74-2,136734-44-6,136734-47-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 10h;

Reference yield: 96.0%

dipterocarpol (471-69-2) → dammarenediol II (14351-29-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 4h; Reflux;

DOI:10.1007/s10600-013-0505-4

upstream raw materials:

dipterocarpol

4-methyl-3-pentenylmagnesium bromide

(1S,4aR,4bR,7S,8aR,10aR)-7-Hydroxy-1,4b,8,8,10a-pentamethyl-1-(4-oxo-pentyl)-dodecahydro-phenanthren-2-one

Phenyl-carbamic acid (3S,5R,8R,9R,10R,14S)-17-acetyl-4,4,8,10,14-pentamethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Downstream raw materials:

C₃₈H₅₆O₅

Refernces

THE ABSOLUTE CONFIGURATION OF C(20) OF DAMMARENEDIOL-I AND -II.

10.1016/S0040-4039(00)70093-1

The study investigates the absolute configuration of C(20) in dammarenediol-I (I) and dammarenediol-II (II). It starts with protopanaxadiol (III), a sapogenin of Ginseng saponins, which upon acid treatment yields panaxadiol (IV). Oxidation of IV leads to a 3-keto derivative (V), which is reduced to 3-deoxy-panaxadiol (VI). Further oxidation of VI gives a 12-keto derivative (VII), which undergoes Saytzeff-Villiger oxidation to form a lactone (VIII). Hydrolysis and methylation of VIII produce an amorphous methyl ester (X), which is dehydrated to an unsaturated ester (XI). Oxidation of XI results in an unsaturated keto ester (XII), which is further oxidized to yield (-) methyl cinamate (XIII). The absolute configuration of (-) linalool (XV) is known to be R, and its derivative (-) cinenic acid (XVI) is methylated to give (-) methyl cinamate. By correlating protopanaxadiol (III) to dammarenediol-I (I), the study concludes that the absolute configuration of C(20) in dammarenediol-I (I) is R and that of dammarenediol-II (II) is S.