Dammarenediol-I

Base Information

Chemical Name:Dammarenediol-I
CAS No.:14351-28-1
Molecular Formula:C₃₀H₅₂O₂
Molecular Weight:444.742
Hs Code.:
DSSTox Substance ID:DTXSID80331607
Nikkaji Number:J20.307F
Wikidata:Q27106331
Metabolomics Workbench ID:28728
Mol file:14351-28-1.mol

Synonyms:Dammarenediol-I;14351-28-1;(+)-24-Dammarene-3beta-20S-diol;Dammarenediol I;CHEBI:4313;DTXSID80331607;LMPR0106080001;(20R)-Dammar-24-ene-3beta,20-diol;(3S,5R,8R,9R,10R,13R,14R,17S)-17-[(2R)-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;C08621;Q27106331

Suppliers and Price of Dammarenediol-I

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Total 3 raw suppliers

Chemical Property of Dammarenediol-I

Chemical Property:

Vapor Pressure:2.02E-13mmHg at 25°C
Boiling Point:529.4°Cat760mmHg
Flash Point:212°C
PSA：40.46000
Density:0.993g/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

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)([C@H]1CC[C@@]2([C@@H]1CC[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C)O)C

Technology Process of Dammarenediol-I

There total 74 articles about Dammarenediol-I 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%

: 128685-91-6,128777-75-3,136734-43-5,136735-34-7
(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

: 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
(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

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

Reference yield: 100.0%

: 128685-91-6,128777-75-3,136734-43-5,136735-34-7
(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

: 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
(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

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

Reference yield:

: 1193-55-1
2-methylcyclohexane-1,3-dione

: 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
(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

Guidance literature:: Multi-step reaction with 28 steps

1: Et₃N / 1,2-dimethoxy-ethane / 23 °C

2: (S)-phenylalanine, (+)-camphorsulfonic acid / dimethylformamide / 576 h / 23 °C

3: 1.) potassium hexamethyldisilazide, Et₃B / 1.) THF, -78 deg C, 2.) -25 deg C, 2 h

4: HgCl₂, water, pyridine / tetrahydrofuran / 36 h / 23 °C

5: Cs₂CO₃ / tetrahydrofuran / 16 h / 23 °C

6: 77 percent / lithium trisiamylborohydride / tetrahydrofuran / -40 °C

7: 1.) n-BuLi / 1.) ether, -20 deg C, 2.) 23 deg C, 12 h

8: 94 percent / C₆H₅NMe₂ / 1 h / 20 °C

9: 1.) Li, liquid NH₃, water / 1.) THF, -40 deg C, 3 min, 2.) -70 deg C, 1 h

10: 0.02percent aq. HCl / acetone / 20 h / 23 °C

11: 1percent aq. KOH / methanol / 6 h / Heating

12: 100 percent / sodium borohydride / tetrahydrofuran; methanol / 1 h / 0 °C

14: 97 percent / methylmagnesium isopropylcyclohexylamide / diethyl ether; toluene / 12 h / 4 °C

15: periodinane / CH₂Cl₂ / 1 h / 23 °C

16: 1.) Li, liquid NH₃, water / 1.) THF, -40 deg C, 3 min, 2.) 30 min

17: 95 percent / NaBH₄ / tetrahydrofuran; methanol / 0 °C

18: 98 percent / imidazole / dimethylformamide / 12 h / 50 °C

19: 94 percent / diphenylbromoborane / CH₂Cl₂ / 0.17 h / -40 °C

20: 95 percent / pyridinium chlorochromate on Al₂O₃ / CH₂Cl₂ / 5 h / 23 °C

22: 92 percent / Li, liquid NH₃, water / tetrahydrofuran / 0.67 h / -50 °C

23: 1.) n-BuLi / 1.) THF, -20 deg C, 2.) 23 deg C, 2 h

24: Li, EtNH₂ / 2-methyl-propan-2-ol / 0.5 h / 0 °C

25: 95 percent / 1percent CF₃CO₂H / tetrahydrofuran; H₂O / 3 h / 23 °C

26: 93 percent / pyridinium chlorochromate on Al₂O₃ / CH₂Cl₂ / 5 h / 20 °C

27: 30 percent / diethyl ether / 0.5 h / 0 °C

28: 100 percent / Bu₄NF / tetrahydrofuran / 10 h / 50 °C

With pyridine; 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; triethyl borane; L-phenylalanine; pyridiniumchlorochromate on aluminumoxide; bromodiphenylborane; tetrabutyl ammonium fluoride; ammonia; water; lithium; potassium hexamethylsilazane; methylmagnesium N-cyclohexylisopropylamide; caesium carbonate; Dess-Martin periodane; ethylamine; N,N-dimethyl-aniline; (+)-10-camphorsulfonic acid; lithium tri-sec-butyl(hydrido)borate; triethylamine; trifluoroacetic acid; mercury dichloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

upstream raw materials:

(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

2-methylcyclohexane-1,3-dione

6-(2-ethyl-[1,3]dioxolan-2-yl)-hex-1-en-3-one

methyl 5-oxoheptanoate

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.

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Encyclopedia

Technology Process of Dammarenediol-I

Dammarenediol-I

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

10.1016/S0040-4039(00)70093-1

NAVIGATION