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(R)-(-)-MUSCONE, also known as muscone, is a chemical compound characterized by its rich and powerful musky aroma. It is known for its pleasant musky scent and is a primary contributor to the odor of musk. (R)-(-)-MUSCONE has been found to possess protective properties against glutamate-induced apoptosis in PC12 cells, indicating potential applications in various industries.

10403-00-6

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10403-00-6 Usage

Uses

Used in Fragrance Industry:
(R)-(-)-MUSCONE is used as a fragrance ingredient for its rich and powerful musky scent, adding a unique and appealing aroma to various perfumes and scented products.
Used in Pharmaceutical Applications:
(R)-(-)-MUSCONE is used as a protective agent for PC12 cells against glutamate-induced apoptosis, suggesting its potential use in the development of treatments for neurodegenerative diseases and other conditions where cell protection is crucial.
Used in Cosmetics Industry:
(R)-(-)-MUSCONE can be used as an additive in the cosmetics industry to provide a distinct and attractive musky scent to various products, such as lotions, creams, and other personal care items.

Check Digit Verification of cas no

The CAS Registry Mumber 10403-00-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,4,0 and 3 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 10403-00:
(7*1)+(6*0)+(5*4)+(4*0)+(3*3)+(2*0)+(1*0)=36
36 % 10 = 6
So 10403-00-6 is a valid CAS Registry Number.
InChI:InChI=1/C16H30O/c1-15-12-10-8-6-4-2-3-5-7-9-11-13-16(17)14-15/h15H,2-14H2,1H3/t15-/m1/s1

10403-00-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (3R)-3-methylcyclopentadecan-1-one

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10403-00-6 SDS

10403-00-6Synthetic route

(3S,4EZ)-3-methylcyclopentadec-4-en-1-one
171034-99-4

(3S,4EZ)-3-methylcyclopentadec-4-en-1-one

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With hydrogen; Crabtree's catalyst In dichloromethane for 4h;99%
(R)-14-methyl-cyclopentadec-2-enone

(R)-14-methyl-cyclopentadec-2-enone

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol99%
(R)-3-methylcyclopentadec-6-en-1-one
213018-22-5

(R)-3-methylcyclopentadec-6-en-1-one

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol98%
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 3h; Catalytic hydrogenation;98%
With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 22h;95%
(-)-(R)-3-methyl-5-cyclopentadecyn-1-one
527722-13-0

(-)-(R)-3-methyl-5-cyclopentadecyn-1-one

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With hydrogen; nickel In ethyl acetate97%
Multi-step reaction with 5 steps
1.1: 100 percent / NaBH4; aq. NaOH / methanol; H2O / 2 h
2.1: PdCl2 / H2O; acetonitrile / 0.5 h / Heating
3.1: aq. HCl / tetrahydrofuran / 2 h / 20 °C
4.1: NEt3; 4-dimethylaminopyridine / CH2Cl2 / 3 h
5.1: toluene / 400 °C
5.2: H2 / [Ir(COD)(py)(PCy3)]*(PF6)(-1) / CH2Cl2 / 4 h
View Scheme
Multi-step reaction with 4 steps
1.1: 100 percent / NaBH4; aq. NaOH / methanol; H2O / 2 h
2.1: PdCl2 / H2O; acetonitrile / 0.5 h / Heating
3.1: NEt3; 4-dimethylaminopyridine / CH2Cl2 / 3 h
4.1: toluene / 400 °C
4.2: H2 / [Ir(COD)(py)(PCy3)]*(PF6)(-1) / CH2Cl2 / 4 h
View Scheme
(R)-3-methyl-1-cyclopentadecenyl propionate

(R)-3-methyl-1-cyclopentadecenyl propionate

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
Stage #1: (R)-3-methyl-1-cyclopentadecenyl propionate With methanol; sodium methylate In toluene at 20℃; for 1h;
Stage #2: With sulfuric acid; water In toluene Product distribution / selectivity;
97%
Product distribution / selectivity;n/a
(R)-3-methyl-1-cyclopentadecenyl acetate

(R)-3-methyl-1-cyclopentadecenyl acetate

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
Stage #1: (R)-3-methyl-1-cyclopentadecenyl acetate With methanol; sodium methylate In toluene at 20℃; for 1h;
Stage #2: With sulfuric acid; water In toluene Product distribution / selectivity;
97%
With methanol; sodium methylate Product distribution / selectivity;92%
Product distribution / selectivity;n/a
(R)-3-methyl-1-cyclopentadecenyl propionate(Z type)

(R)-3-methyl-1-cyclopentadecenyl propionate(Z type)

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
Stage #1: (R)-3-methyl-1-cyclopentadecenyl propionate(Z type) With methanol; sodium methylate In toluene at 20℃; for 1h;
Stage #2: With sulfuric acid In water; toluene Product distribution / selectivity;
97%
(R)-3-methyl-1-cyclopentadecenyl acetate(E type)

(R)-3-methyl-1-cyclopentadecenyl acetate(E type)

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
97%
O-(7R)-7-methyl-5-oxocyclopentadecyl O-phenyl carbonothioate
1095567-32-0

O-(7R)-7-methyl-5-oxocyclopentadecyl O-phenyl carbonothioate

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 4h; Reflux; Inert atmosphere;97%
(2E)-cyclopentadec-2-en-1-one
56345-01-8

(2E)-cyclopentadec-2-en-1-one

methyllithium
917-54-4

methyllithium

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With copper(l) iodide; (1R,2R,3S,4S)-3-<(1-methylpyrrol-2-yl)methylamino>-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol In tetrahydrofuran; toluene at -78℃; Mechanism; Product distribution; chiral amplification; enantioselectivity;93%
With copper(l) iodide; (1R,2R,3S,4S)-3-<(1-methylpyrrol-2-yl)methylamino>-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol In tetrahydrofuran; toluene at -78℃;93%
With tetrahydrofuran; copper(l) iodide; (1R)-2-endo-hydroxy-3-endo-<<(N-methylpyrrol-2-yl)methyl>amino>-1,7,7-trimethylbicyclo<2.2.1>heptan In toluene at -78℃; Product distribution; multistep reaction; var. solvents and chiral additives;89%
(2R,3R,7R)-N,N'-dibenzyl-7-methyl-1,4-dioxa-spiro[4.14]nonadecane-2,3-dicarboxamide
824402-15-5

(2R,3R,7R)-N,N'-dibenzyl-7-methyl-1,4-dioxa-spiro[4.14]nonadecane-2,3-dicarboxamide

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,4-dioxane; water at 80℃; for 3h;93%
(3R)-3-methylcyclopentadec-5-enone
391207-98-0

(3R)-3-methylcyclopentadec-5-enone

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 20℃; for 1h;92%
C34H50O4

C34H50O4

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With hydrogenchloride; water92%
(1S, 15S)-bicyclo<13.1.0>hexadecan-2-one
102521-18-6

(1S, 15S)-bicyclo<13.1.0>hexadecan-2-one

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With ammonia; lithium In diethyl ether at -78℃;82%
With dipyridinium dichromate; ammonia; lithium; tert-butyl alcohol 1.) ether, reflux (-33 deg C), 0.5 h, 2.) CH2Cl2, RT, 27.5 h; Yield given. Multistep reaction;
zirconocene methyl chloride

zirconocene methyl chloride

(2E)-cyclopentadec-2-en-1-one
56345-01-8

(2E)-cyclopentadec-2-en-1-one

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
Stage #1: zirconocene methyl chloride With (11bS)-N-cyclohexyl-N-((S)-1,2,3,4-tetrahydronaphthalen-1-yl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine; silver trifluoromethanesulfonate; copper(l) chloride In diethyl ether; dichloromethane at 0℃; for 0.0833333h; Darkness; Inert atmosphere;
Stage #2: (2E)-cyclopentadec-2-en-1-one With chloro-trimethyl-silane In diethyl ether; dichloromethane at 0℃; for 0.333333h; Inert atmosphere; Darkness; stereoselective reaction;
82%
(1R,3R)-3-methylcyclopentadecanol
477724-64-4

(1R,3R)-3-methylcyclopentadecanol

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With dipyridinium dichromate In dichloromethane at 20℃; for 48h;81%
(6R)-2,6-dimethyl-2,17-octadecadien-8-one
213018-18-9

(6R)-2,6-dimethyl-2,17-octadecadien-8-one

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
Stage #1: (6R)-2,6-dimethyl-2,17-octadecadien-8-one With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-ethane at 50℃; for 11h;
Stage #2: With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; for 9h;
74%
Multi-step reaction with 2 steps
1: Grubbs Catalyst 2nd Generation / CH2Cl2 / 12 h / 65 °C
2: H2 / Pd/C / ethanol / 2.5 h / 30 °C / 760 Torr
View Scheme
Multi-step reaction with 2 steps
1: 29 mg / H2 / (PCy3)Cl2[N,N'-Mes2-imidazolidin-2-yl]Ru=CHPh / 1,2-dichloro-ethane / 24 h / 80 °C / 41372.9 Torr
View Scheme
C18H34S2
1266679-07-5

C18H34S2

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With iodine; sodium hydrogencarbonate In water; acetone for 0.25h; Cooling with ice;72%
C18H32O3

C18H32O3

A

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

B

(+)-(2R)-2-methylcyclopentadecanone
52914-66-6, 77857-86-4, 77857-73-9

(+)-(2R)-2-methylcyclopentadecanone

Conditions
ConditionsYield
Stage #1: C18H32O3 With methanol; water; sodium hydroxide for 5h; Reflux;
Stage #2: With hydrogenchloride; methanol; water for 1h; Reflux;
A 12%
B 66%
cyclopentadec-2-en-1-one
32247-08-8

cyclopentadec-2-en-1-one

A

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

B

(S)-muscone
63975-98-4

(S)-muscone

Conditions
ConditionsYield
Stage #1: dimethyl zinc(II); 4-(cis-2,6-dimethylpiperidine)-(R)-dinaphthdioxaphosphepin; copper compound In toluene
Stage #2: cyclopentadec-2-en-1-one In toluene Product distribution / selectivity;
A 60.7%
B n/a
(2E)-cyclopentadec-2-en-1-one
56345-01-8

(2E)-cyclopentadec-2-en-1-one

dimethyl zinc(II)
544-97-8

dimethyl zinc(II)

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
Stage #1: (2E)-cyclopentadec-2-en-1-one; dimethyl zinc(II) With 4-(cis-2,6-dimethylpiperidine)-(R)-ditetrahydronaphthdioxaphosphepin; copper(II) bis(trifluoromethanesulfonate) In toluene at -20℃; for 4.08333h;
Stage #2: With methanol; sodium methylate In toluene Product distribution / selectivity;
53%
(3R)-3-methyl-5-oxocyclopentadecanecarboxaldehyde
119708-23-5

(3R)-3-methyl-5-oxocyclopentadecanecarboxaldehyde

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
With RhCl(PPh3)3 In benzene for 8h; Heating;40%
With Wilkinson's catalyst
(R)-14-Methyl-2-cyclopentadecynon
68380-94-9

(R)-14-Methyl-2-cyclopentadecynon

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
(hydrogenation);
(2E)-cyclopentadec-2-en-1-one
56345-01-8

(2E)-cyclopentadec-2-en-1-one

methyllithium
917-54-4

methyllithium

A

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

B

(S)-muscone
63975-98-4

(S)-muscone

Conditions
ConditionsYield
With copper(l) iodide; (1R,2R,3S,4S)-3-<(1-methylpyrrol-2-yl)methylamino>-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol In diethyl ether; toluene at -78℃; Product distribution; other chiral ligands, var. solvents, and ratios cuprate to educt;
With copper(l) iodide; (1R,2R,3S,4S)-3-<(1-methylpyrrol-2-yl)methylamino>-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol 1.) toluene, ether, 2.) -78 deg C; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
copper(l) iodide; (1R,2R,3S,4S)-3-<(1-methylpyrrol-2-yl)methylamino>-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol; lithium bromide In diethyl ether; toluene at -78℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
(R)-2-Methyl-15-oxo-cyclopentadecanecarboxylic acid

(R)-2-Methyl-15-oxo-cyclopentadecanecarboxylic acid

A

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

B

(S)-muscone
63975-98-4

(S)-muscone

Conditions
ConditionsYield
at 50℃;
(1S, 15S)-bicyclo<13.1.0>hexadecan-2-one
102521-18-6

(1S, 15S)-bicyclo<13.1.0>hexadecan-2-one

A

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

B

(3R)-3-methylcyclopentadecan-1-ol
62151-56-8

(3R)-3-methylcyclopentadecan-1-ol

Conditions
ConditionsYield
With ammonia; lithium; tert-butyl alcohol In diethyl ether at -33℃; for 0.5h;
(E)-1-[(S)-2-Methyl-3-(toluene-4-sulfonyl)-propyl]-cyclododecene
62221-80-1, 62221-81-2, 63975-88-2, 63975-92-8

(E)-1-[(S)-2-Methyl-3-(toluene-4-sulfonyl)-propyl]-cyclododecene

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

Conditions
ConditionsYield
Multistep reaction;
methanol
67-56-1

methanol

(R)-3-methyl-1-cyclopentadecanone
10403-00-6

(R)-3-methyl-1-cyclopentadecanone

(+)-(1Z,3R)-methyl 3-methylcyclotetradec-1-ene-1-carboxylate
1370650-06-8

(+)-(1Z,3R)-methyl 3-methylcyclotetradec-1-ene-1-carboxylate

Conditions
ConditionsYield
With iodine; potassium hydroxide at -5 - 0℃; Favorskii rearrangement; stereospecific reaction;56%

10403-00-6Relevant articles and documents

Copper-catalyzed conjugate addition on macrocyclic, cyclic, and acyclic enones with a chiral phosphoramidite ligand having a C2-symmetric amine moiety

Choi, Yong Hyun,Choi, Jun Young,Yang, Hye Yon,Kim, Yong Hae

, p. 801 - 804 (2002)

A binaphthol-based phosphoramidite ligand (4.2 mol%) having a C2-symmetric chiral amine moiety was examined for enantioselective 1,4-additions of dialkylzinc reagents to various macrocyclic, cyclic, and acyclic enones catalyzed by copper triflate·toluene complex (2 mol%) to afford high enantiomeric excess (up to >95% ee).

Efficient synthesis of (-)-(R)-muscone by enantioselective protonation

Fehr, Charles,Galindo, Jose,Farris, Iris,Cuenca, Ana

, p. 1737 - 1747 (2004)

A new synthesis of (-)-(R)-muscone ((R)-1) by means of enantioselective protonation of a bicyclic ketone enolate as the key step (see 6 → (S)-4 in Scheme 2) is presented. The C15 macrocyclic system is obtained by ozonolysis (Scheme 7).

Ring closing metathesis guided synthesis of (R)-(-)-muscone

Kamat, Vijayendra P.,Hagiwara, Hisahiro,Suzuki, Toshio,Ando, Masayoshi

, p. 2253 - 2254 (1998)

A concise synthesis of the valuable perfumery compound (R)-(-)-muscone 1 in its natural form by making use of the ring closing olefin metathesis (RCM)-aided macrocyclisation route has been achieved.

Cp2ZrMeCl: A Reagent for Asymmetric Methyl Addition

Garrec, Kilian,Fletcher, Stephen P.

, p. 3814 - 3817 (2016)

The use of Cp2ZrMeCl is described as a source of nucleophilic methyl in asymmetric catalysis. This easily prepared reagent is bench stable, weighable in air, and generally useful in highly enantioselective copper-catalyzed addition reactions at room temperature. Methyl is successfully (generally >90% ee) added in 1,4-additions to cyclic and acyclic α,β-unsaturated ketones to provide tertiary and quaternary centers. Examples of catalyst controlled diastereoselective 1,6-addition and dynamic kinetic asymmetric allylic alkylation reactions are also reported. The reagent is used in the catalytic asymmetric synthesis of naturally occurring fragrance (R)-(-)-muscone (82% yield, 91% ee).

Deoxycholic acid-based phosphites as chiral ligands in the enantioselective conjugate addition of dialkylzincs to cyclic enones: Preparation of (-)-(R)-muscone

Iuliano, Anna,Scafato, Patrizia,Torchia, Rita

, p. 2533 - 2538 (2004)

Four phosphites, obtained by linking enantiomerically pure binaphthylchlorophosphite to the two different hydroxy substituted positions of deoxycholic acid, were used as chiral ligands in the enantioselective copper catalysed 1,4-addition of diethylzinc to 2-cyclohexenone and dimethylzinc to 2-cyclopentadecenone. Various reaction parameters were changed in order to select the experimental conditions that would maximise yield and ee. The four ligands were screened for activity and enantioselectivity under the optimised reaction conditions for comparative purposes, in order to establish the influence of the absolute configuration of the binaphthyl moiety as well as the position on the cholestanic backbone of the phosphite moiety. The ligand possessing a (R)-binaphthylphosphite moiety at position 12 of the cholestanic backbone proved to be the most enantioselective affording (-)-(R)-muscone in 63% ee.

Asymmetric conjugate addition of metal alkyl reagents catalyzed by copper complexes with BINPO: A hemilabile P,O-heterobidentate axially chiral ligand

Fuchs, Nicolas,D'Augustin, Magali,Humam, Munir,Alexakis, Alexandre,Taras, Rossana,Gladiali, Serafino

, p. 3143 - 3146 (2005)

We herein report the use of a new class of P,O-bidentate arylphosphine ligand for the asymmetric copper catalyzed conjugate addition of dialkylzinc and trialkylaluminium with the enantiomeric excesses reaching 91% while (R)-muscone was obtained with 77% ee.

Synthesis of (R)-(-)- and (S)-(+)-Muscone of 100percent Optical Purity by Conjugate Addition of Chiral Methylcuprate to (E)-Cyclopentadec-2-enone

Tanaka, Kazuhiko,Suzuki, Hitomi

, p. 101 - 102 (1991)

Synthesis of (R)-(-)- and (S)-(+)-muscone of essentially 100percent enantiomeric excess (e.e.) by the conjugate addition of chiral methylcuprate to (E)-cyclopentadec-2-enone was accomplished by adding small amounts of tetrahydrofuran (THF) as an external ligand to a toluene solution of the chiral methylcuprate.

Synthesis of (R)-(-)-muscone via enzymatic resolution of 3- methylcyclopentadecan-1-ol

Matsumura, Yasufumi,Fukawa, Hidemichi,Terao, Yoshiyasu

, p. 1484 - 1485 (1998)

(R)-(-)-Muscone was synthesized efficiently by oxidation of 3-(R)- methylcyclopentadecan-1-(RS)-ol, which was obtained by lipase-catalyzed resolution of its diastereomeric mixture.

Practical optical resolution of dl-muscone using tartaric acid derivatives as a chiral auxiliary

Takabe, Kunihiko,Sugiura, Masataka,Asumi, Yuya,Mase, Nobuyuki,Yoda, Hidemi,Shimizu, Hiroyasu

, p. 3457 - 3460 (2005)

A simple and practical synthesis of (R)-(-)-muscone was achieved by optical resolution of dl-muscone using tartaric acid derivatives. The acetalization of dl-muscone with N,N′-dibenzyl-l-tartaramide in the presence of Sc(OTf)3 and methyl orthoformate furnished a diastereomeric mixture of acetals, which were readily separated by simple recrystallization. Diastereomerically pure acetal was hydrolyzed to give optically pure muscone and recovered N,N′-dibenzyl-l-tartaramide.

A novel synthetic method for (R)- and (S)-muscones by enantioselective hydrogenation of (E)- and (Z)-3-methyl-2-cyclopentadecen-1-ones catalyzed by p-tolyl-BINAP-Ru(II) complexes

Yamamoto, Takeshi,Ogura, Miharu,Kanisawa, Tsuneyoshi

, p. 9209 - 9212 (2002)

A novel and practical synthesis of (R)- and (S)-muscones by the asymmetric hydrogenation of (E)- and (Z)-3-methyl-2-cyclopentadecen-1-ones catalyzed by p-tolyl-BINAP-Ru(II) complexes has been achieved in nearly complete enantioselectivity.

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