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Hangzhou Viablife Biotech CO.,LTD

Viablife has a world-class R&D team that has a broad range of experience in fermentation , enzymes,metabolic engineering and synthetic biology . Viablife has its own manufacturing center,Jiangxi Viablife Biopharmaceutical Co.,Ltd, a wholly own

Squalene cas :111-02-4/ 7683-64-9

Cas:111-02-4

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Trading Company

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Dayang Chem (Hangzhou) Co.,Ltd.

As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem's R&D center offer custom synthesis services. DayangChem can provide different quantities of custom synthesis ch

(all-E)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene

Cas:111-02-4

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

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Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

High quality Squalene supplier in China

Cas:111-02-4

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

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Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

High Quality 99% Squalene 111-02-4 GMP manufacturer

Cas:111-02-4

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

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Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

Squalene

Cas:111-02-4

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Henan Tianfu Chemical Co., Ltd.

Our company engages in Sodium Tripolyphosphate (STPP) and Sodium Hexametabphosphate (SHMP) production; development of noble metal catalysts, synthesis of electronic chemical materials and general chemicals Imp&Exp trading business. The company

TIANFU-CHEM -(all-E)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene

Cas:111-02-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Hebei Nengqian Chemical Import and Export Co., LTD

Our Advantage Rich Experience Our products are sold all over Europe,North&South America, Sino-East, Asia and pacific area as well as Africa,we establish long term. Quality service Company cooperates with research institutes. We strictly con

111-02-4 Squalene

Cas:111-02-4

Min.Order:1 Kilogram

FOB Price: $15.0 / 50.0

Type:Trading Company

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Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

Wholesale price CAS 111-02-4 with best price

Cas:111-02-4

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Hebei Sankai Chemical Technology Co., Ltd

1. Product advantages ♦ High purity, all above 98.5%, no impurities after dissolution ♦ We will test each batch to ensure quality ♦ OEM and private brand services designed for free ♦ Various cap colors available ♦ W

Squalene CAS111-02-4

Cas:111-02-4

Min.Order:1 Kilogram

FOB Price: $7.0 / 9.0

Type:Trading Company

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Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

2,6,10,14,18,22-Tetracosahexaene,2,6,10,15,19,23-hexamethyl-, (2E,6E,10E,14E,18E)- 111-02-4

Cas:111-02-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Xi'an Faithful Biotech Co., Ltd.

We are the manufacturers and suppliers of API in China, and warehouse in Germany and USA of California, which can quickly and safely deliver to your address 1.High quality and competitive price. 2.Free sample for your evaluation. 3.Promptly delivery

99% Purity squalene Factory Supply Pure All-trans-Squalene Pure

Cas:111-02-4

Min.Order:10 Gram

FOB Price: $3.5

Type:Trading Company

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Zhonghe Fountain(Tianjin)Biotech Ltd.

Zhonghe Fountain is striving for R&D,production and distribution cosmetic active ingredients for personal care industry. Zhonghe Fountain always maintains a keen insight into industry and focuses on the market demand trends to expand its invests

Skin Moisturizing Antioxidant Active Ingredient Squalene

Cas:111-02-4

Min.Order:1 Kilogram

FOB Price: $25.0 / 80.0

Type:Trading Company

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Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

2,6,10,14,18,22-Tetracosahexaene,2,6,10,15,19,23-hexamethyl-, (2E,6E,10E,14E,18E)-

Cas:111-02-4

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Hangzhou Keyingchem Co.,Ltd

Hangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det

Squalene

Cas:111-02-4

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

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Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

(E,E,E,E)-Squalene

Cas:111-02-4

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Zibo Dorne chemical technology co. LTD

Product Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,

High purity Squalene

Cas:111-02-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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TAIZHOU ZHENYU BIOTECHNOLOGY CO., LTD

Zhenyu biotech exported this product to many countries and regions at best price. if you are looking for the material's manufacturer or supplier in china, zhenyu biotech is your best choice. pls contact with us freely for getting detailed

Squalene

Cas:111-02-4

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Lab/Research institutions

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Kono Chem Co.,Ltd

high purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:drum and bag Application:for pharma use Transportation:by sea or air Port:Beijing or Guangzhou

(E,E,E,E)-squalene

Cas:111-02-4

Min.Order:0

Negotiable

Type:Other

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Shanghai Acmec Biochemical Technology Co., Ltd.

Acmec is a leading manufacturer and supplier of biochemical reagents and life science products. We have over 40,000 items in stock (real-time inventory) and offer discounted prices to registered members of the online store ( www.acmec.com.cn ) Appea

Acmec Squalene S75661 20mg

Cas:111-02-4

Min.Order:1 bottle

Negotiable

Type:Lab/Research institutions

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Henan Allgreen Chemical Co.,Ltd

high quality Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea

Squalene

Cas:111-02-4

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Aecochem Corp.

Our clients, like BASF,CHEMO,Brenntag,ASR,Evonik,Merck and etc.Appearance:COA Storage:in stock Application:MSDS/TDS

Squalene

Cas:111-02-4

Min.Order:0

Negotiable

Type:Manufacturers

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Chengdu Lemeitian Pharmaceutical Technology Co,. Ltd

ADVANTAGE:1. More than 3,000 Chinese medicine reference substances / standard products available from stock, issued on the same day, multiple cities can be delivered the next day2. The products are provided with COA, HPLC, NMR, quality assurance, pac

Squalene

Cas:111-02-4

Min.Order:0

Negotiable

Type:Manufacturers

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Xi`an Eastling Biotech Co., Ltd.

high purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:Foil bag; Drum; Plastic bottle Application:Pharma;Industry;Agricultural Transportation:by sea or air Port:Beijing or Guangzhou

Squalene

Cas:111-02-4

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Chemsigma International Co.,Ltd.

bulk productiongoods in stockswe have the best competitive price in the marketmeantime,we are committed to service to our every customer Chemsigma International Co.,Ltd. is a chemical manufacturer, specialize in custom synthesis and organic chemical

(all-E)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene

Cas:111-02-4

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Hangzhou Huarong Pharm Co., Ltd.

High qualityAppearance:White powder Storage:Room temperature Package:Aluminum bag Application:Used in producing API Transportation:By air Port:Beijing

Squalene

Cas:111-02-4

Min.Order:0

Negotiable

Type:Trading Company

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Antimex Chemical Limied

Ansciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali

Squalene

Cas:111-02-4

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Xiamen AmoyChem Co.,Ltd

Amoychem is committed to providing the top-quality chemical products and services Internationally. We offer our customers with friendly, professional service and reliable, high performance products that have been manufactured according to the accredi

Squalene

Cas:111-02-4

Min.Order:0

Negotiable

Type:Other

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HANGZHOU TIANYE CHEMICALS CO., LTD.

We product this chemical more than 10 years . We are very experience to export it to many countries, Our superior & stable quality , competitive price gain warm reception from our customers. Application:Chemical intermediate

(6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyltetracosa-2,6,10,14,18,22-hexaene

Cas:111-02-4

Min.Order:0

Negotiable

Type:Trading Company

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Guangdong Juda Chemical Industrial Co.,Limited

Factory supply high purity low priceAppearance:solid or liquid Storage:sealed in cool and dry place Package:As customer's requested Application:Pharma Intermediate Transportation:by courier/air/sea Port:Any port in China

Squalene CAS No.111-02-4

Cas:111-02-4

Min.Order:0

Negotiable

Type:Trading Company

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Synthetic route

C36H54O2S

C36H54O2S

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
With bis(diphenylphosphino)propanepalladium(II) dichloride; lithium triethylborohydride In tetrahydrofuran at -78 - 20℃; for 50h;88.7%
Farnesol
106-28-5

Farnesol

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

(6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene
3899-18-1

(6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene

C

(E)-3,7,11-trimethyldodeca-1,6,10-triene
66633-32-7

(E)-3,7,11-trimethyldodeca-1,6,10-triene

Conditions
ConditionsYield
With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 2h; Solvent; Inert atmosphere; Reflux; regioselective reaction;A 9%
B 8%
C 78%
[(6E,10E,14E,18E)-13-(1-ethoxyethoxy)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-12-yl]sulfonylbenzene
1299297-72-5

[(6E,10E,14E,18E)-13-(1-ethoxyethoxy)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-12-yl]sulfonylbenzene

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
With (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride In tetrahydrofuran; 1,4-dioxane at 20 - 70℃; for 10h; Inert atmosphere;77%
Conditions
ConditionsYield
With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate at -78℃;70%
With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate In toluene at -78℃; for 12h;70%
Farnesol
106-28-5

Farnesol

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
Stage #1: Farnesol With tert.-butyl lithium In tetrahydrofuran; n-heptane at -78 - 20℃; for 0.333333h; Inert atmosphere;
Stage #2: With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 10h; Inert atmosphere; Reflux;
67%
Multi-step reaction with 2 steps
1: PBr3 / tetrahydrofuran / 0.5 h / 0 °C
2: CuI; pyrrolidine; n-BuLi / diethyl ether / 1 h / -38 °C
View Scheme
Multi-step reaction with 2 steps
1: PBr3 / tetrahydrofuran / 0.5 h / 0 °C
2: CuI; pyrrolidine; n-BuLi / diethyl ether / 1 h / -38 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / CH2Cl2 / 0.5 h / -40 °C
2: lithium bromide / CH2Cl2; tetrahydrofuran / 1 h / 0 °C
3: 1) lithium biphenylide, barium iodide / 1) THF, -78 deg C, 30 min, 2) THF, a) -78 deg C, 3 h, b) 23 deg C, 16 h
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / CH2Cl2 / 0.5 h / -40 °C
2: lithium chloride / CH2Cl2; tetrahydrofuran / 1 h / 0 °C
3: 1) lithium biphenylide, barium iodide / 1) THF, -78 deg C, 30 min, 2) THF, a) -78 deg C, 3 h, b) 23 deg C, 16 h
View Scheme
C22H25NO5S

C22H25NO5S

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane; triphenylphosphine; palladium dichloride In tetrahydrofuran at 20℃; for 16h; Wurtz type coupling reaction; Inert atmosphere; stereoselective reaction;60%

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

(6E,14E)-2,6,10,11,15,19-Hexamethyl-10,11-divinyl-icosa-2,6,14,18-tetraene
86342-81-6

(6E,14E)-2,6,10,11,15,19-Hexamethyl-10,11-divinyl-icosa-2,6,14,18-tetraene

C

(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene
86342-79-2

(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

Conditions
ConditionsYield
With chlorotris(triphenylphosphine)cobalt(I) In benzene for 0.5h; Ambient temperature;A 55%
B 12%
C 22%
With chlorotris(triphenylphosphine)cobalt(I) In benzene for 3h; Ambient temperature;A 55%
B 12%
C 22%
Farnesol
106-28-5

Farnesol

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

(E)-3,7,11-trimethyldodeca-1,6,10-triene
66633-32-7

(E)-3,7,11-trimethyldodeca-1,6,10-triene

Conditions
ConditionsYield
With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 6h; Inert atmosphere; Reflux;A 23%
B 42%
With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran for 4h; Time; Inert atmosphere; Reflux;A 36%
B 24%
3,12-dibromo-10-ethyl-2,6-dimethyl-dodeca-6,10-dien-2-ol

3,12-dibromo-10-ethyl-2,6-dimethyl-dodeca-6,10-dien-2-ol

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

3-((3E,7E,11E,15E)-7-Ethyl-3,12,16,20-tetramethyl-henicosa-3,7,11,15,19-pentaenyl)-2,2-dimethyl-oxirane

3-((3E,7E,11E,15E)-7-Ethyl-3,12,16,20-tetramethyl-henicosa-3,7,11,15,19-pentaenyl)-2,2-dimethyl-oxirane

C

C32H54O2

C32H54O2

Conditions
ConditionsYield
With copper(l) iodide; lithium pyrrolidideA 15%
B 33%
C 10%
4-{Phenyl-[(3E,7E)-4,8,12-trimethyl-1-((1E,5E)-2,6,10-trimethyl-undeca-1,5,9-trienyl)-trideca-3,7,11-trienyl]-phosphinoyl}-morpholine
130673-53-9

4-{Phenyl-[(3E,7E)-4,8,12-trimethyl-1-((1E,5E)-2,6,10-trimethyl-undeca-1,5,9-trienyl)-trideca-3,7,11-trienyl]-phosphinoyl}-morpholine

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
With lithium; ethylamine; tert-butyl alcohol In tetrahydrofuran at 0℃; for 2.5h;31%
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
With diethyl ether; lithium
(2E,6E)-farnesyl acetate
4128-17-0

(2E,6E)-farnesyl acetate

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

(6E,10Z,14Z,18E)-squalene
56782-22-0

(6E,10Z,14Z,18E)-squalene

C

(6E,10Z,16E)-2,6,10,13,17,21-Hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene
86342-80-5

(6E,10Z,16E)-2,6,10,13,17,21-Hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

D

(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene
86342-79-2

(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper; zinc; molybdenum hexacarbonyl In 1,4-dioxane for 115h; Heating; Yield given. Further byproducts given. Yields of byproduct given;
(2E,6E)-farnesyl acetate
4128-17-0

(2E,6E)-farnesyl acetate

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

(6E,10Z,16E)-2,6,10,13,17,21-Hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene
86342-80-5

(6E,10Z,16E)-2,6,10,13,17,21-Hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

C

(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene
86342-79-2

(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

D

(5E,9Z,13Z,17E)-2,5,9,14,18,21-Hexamethyl-docosa-2,5,9,13,17,20-hexaene

(5E,9Z,13Z,17E)-2,5,9,14,18,21-Hexamethyl-docosa-2,5,9,13,17,20-hexaene

Conditions
ConditionsYield
With zinc; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; methanol for 2.5h; Ambient temperature; Yield given. Further byproducts given. Yields of byproduct given;
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
With lithium biphenylide; barium(II) iodide 1) THF, -78 deg C, 30 min, 2) THF, a) -78 deg C, 3 h, b) 23 deg C, 16 h; Yield given. Multistep reaction;
(E)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate
85611-33-2

(E)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl acetate

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

squalene
24566-13-0

squalene

C

(6E,10Z,14Z,18E)-squalene
56782-22-0

(6E,10Z,14Z,18E)-squalene

D

(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene
86342-79-2

(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

Conditions
ConditionsYield
With [2,2]bipyridinyl; zinc; molybdenum hexacarbonyl In 1,4-dioxane for 72h; Heating; Yield given. Further byproducts given. Yields of byproduct given;
With [2,2]bipyridinyl; zinc; molybdenum hexacarbonyl In 1,4-dioxane for 72h; Heating; Yield given. Further byproducts given. Yields of byproduct given;

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene
86342-79-2

(6E,10E,16E)-2,6,10,13,17,21-hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

Conditions
ConditionsYield
With lithium biphenylide; barium(II) iodide In tetrahydrofuran at -78℃; for 1h; Yield given. Yields of byproduct given;
With lithium biphenylide; barium(II) iodide In tetrahydrofuran at -78℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Farnesyl diphosphate

Farnesyl diphosphate

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
With PP1; Tween-80 Kinetics; Mechanism; buffer (KF, MgCl2, DTT, NADHP);
Presqualene diphosphate

Presqualene diphosphate

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
With (ammonium analogue); inhib. phosphonophosphate 8 Kinetics; Mechanism;
1-((6E,10E,14E,18E)-2,6,10,14,18,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-12-sulfonyl)-4-methyl-benzene

1-((6E,10E,14E,18E)-2,6,10,14,18,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-12-sulfonyl)-4-methyl-benzene

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

squalene
24566-13-0

squalene

Conditions
ConditionsYield
With lithium triethylborohydride; bis(diphenylphosphino)propanepalladium(II) dichloride In tetrahydrofuran at 0℃; Yield given. Yields of byproduct given;
Farnesol
106-28-5

Farnesol

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

(6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-5-thiol

(6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-5-thiol

C

(6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-12-thiol

(6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-12-thiol

D

(6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-9-thiol

(6E,10E,14E,18E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaene-9-thiol

Conditions
ConditionsYield
With iron sulfide; hydrogen sulfide In water at 100℃; under 1500.1 Torr; for 144h; Yield given;
3,6-dichloro-octane-2,7-dione
99548-50-2

3,6-dichloro-octane-2,7-dione

homogeranyl lithium

homogeranyl lithium

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
With diethyl ether at -70℃; Behandeln des Reaktionsprodukts mit methanol.Kalilauge, dann mit Natriumjodid und Natriumacetat in Essigsaeure und Propionsaeure bei -20grad bis +20grad; dann mit Zinn(II)-chlorid in Aether und Pyridin und mit Phosphoroxychlorid;
P,P,P,P',P',P'-hexaphenyl-butane-1,4-diyldiphosphonium dibromide

P,P,P,P',P',P'-hexaphenyl-butane-1,4-diyldiphosphonium dibromide

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
With tetrahydrofuran; n-butyllithium; diethyl ether Erwaermen des Reaktionsprodukts mit 6,10-Dimethyl-undeca-5t,9-dien-2-on;
Botryococcus braunii

Botryococcus braunii

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

(3S,7S,10S,13R,16S,20S)-2,3,7,10,13,16,20,21-octamethyl-6,17-bis-methylene-10-vinyl-docosa-1,11t,21-triene
42719-34-6

(3S,7S,10S,13R,16S,20S)-2,3,7,10,13,16,20,21-octamethyl-6,17-bis-methylene-10-vinyl-docosa-1,11t,21-triene

C

(6E,11E,16E)-2,6,10,13,17,21-hexamethyl-10-vinyldocosa-2,6,11,16,20-pentaene
88361-07-3, 127483-82-3, 127483-86-7

(6E,11E,16E)-2,6,10,13,17,21-hexamethyl-10-vinyldocosa-2,6,11,16,20-pentaene

D

showacene

showacene

Conditions
ConditionsYield
With sodium <14C>bicarbonate Further byproducts given. Title compound not separated from byproducts;
Botryococcus braunii

Botryococcus braunii

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

(3S,7S,10S,13R,16S,20S)-2,3,7,10,13,16,20,21-octamethyl-6,17-bis-methylene-10-vinyl-docosa-1,11t,21-triene
42719-34-6

(3S,7S,10S,13R,16S,20S)-2,3,7,10,13,16,20,21-octamethyl-6,17-bis-methylene-10-vinyl-docosa-1,11t,21-triene

C

(6E,11E,16E)-2,6,10,13,17,21-hexamethyl-10-vinyldocosa-2,6,11,16,20-pentaene
88361-07-3, 127483-82-3, 127483-86-7

(6E,11E,16E)-2,6,10,13,17,21-hexamethyl-10-vinyldocosa-2,6,11,16,20-pentaene

D

darwinene

darwinene

Conditions
ConditionsYield
With sodium <14C>bicarbonate Further byproducts given. Title compound not separated from byproducts;
Botryococcus braunii

Botryococcus braunii

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

(6E,11E,16E)-2,6,10,13,17,21-hexamethyl-10-vinyldocosa-2,6,11,16,20-pentaene
88361-07-3, 127483-82-3, 127483-86-7

(6E,11E,16E)-2,6,10,13,17,21-hexamethyl-10-vinyldocosa-2,6,11,16,20-pentaene

C

showacene

showacene

D

darwinene

darwinene

Conditions
ConditionsYield
With sodium <14C>bicarbonate Further byproducts given. Title compound not separated from byproducts;

A

(6E,10E,16E)-2,6,10,13,17,21-Hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

(6E,10E,16E)-2,6,10,13,17,21-Hexamethyl-13-vinyl-docosa-2,6,10,16,20-pentaene

B

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

C

Squalene

Squalene

Conditions
ConditionsYield
With manganese; bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran at 20℃;
trans-geranyl bromide
6138-90-5

trans-geranyl bromide

A

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

B

digeranyl
35162-77-7

digeranyl

C

2,6,10,15,19-pentamethyleicosa-(6E,10E,14E)-2,6,10,14,18-pentaene
38235-83-5

2,6,10,15,19-pentamethyleicosa-(6E,10E,14E)-2,6,10,14,18-pentaene

Conditions
ConditionsYield
With pyrrolidine; copper(l) iodide; n-butyllithium In diethyl ether at -38℃; for 1h;A n/a
B 20 mg
C 28 mg
prenyl bromide
870-63-3

prenyl bromide

A

2,6,10,15-tetramethylhexadeca-(6E,10E)-2,6,10,14-tetraene

2,6,10,15-tetramethylhexadeca-(6E,10E)-2,6,10,14-tetraene

B

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
With pyrrolidine; copper(l) iodide; n-butyllithium In diethyl ether at -38℃; for 1h;
Geraniol
106-24-1

Geraniol

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: PBr3 / tetrahydrofuran / 0.5 h / 0 °C
2: CuI; pyrrolidine; n-BuLi / diethyl ether / 1 h / -38 °C
View Scheme
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

2,6,10,15,19,23-hexamethyltetracosane
111-01-3

2,6,10,15,19,23-hexamethyltetracosane

Conditions
ConditionsYield
With hydrogen In ethanol at 50℃; under 760.051 Torr; for 6h; Reagent/catalyst; Temperature; Solvent; chemoselective reaction;99.6%
With hydrogen; nickel
With palladium 10% on activated carbon; hydrogen In ethanol at 100℃; under 3750.38 Torr; for 1h; Autoclave;
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

2,3,22,23-Dioxidosqualene
654052-53-6

2,3,22,23-Dioxidosqualene

Conditions
ConditionsYield
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With N-Bromosuccinimide; water In tetrahydrofuran for 3h;
Stage #2: With potassium carbonate In methanol for 2h; Further stages.;
90%
With potassium carbonate; 3-chloro-benzenecarboperoxoic acid or NBS; Multistep reaction;
Multi-step reaction with 2 steps
1: 22 percent / dimethyldioxirane
2: 60 percent / methyl(trifluoromethyl)dioxirane
View Scheme
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

(rac)-hexaepoxysqualene
10008-64-7

(rac)-hexaepoxysqualene

Conditions
ConditionsYield
With polyoxotungstate PW4O24[methyltri((C8-C10)alkyl)ammonium]3 In water at 20℃; for 12h; pH=7.0; Green chemistry;89%
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

(3R)-2,3-isopropylidenedioxy-2,3-dihydrosqualene
642093-28-5

(3R)-2,3-isopropylidenedioxy-2,3-dihydrosqualene

Conditions
ConditionsYield
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With potassium osmate(VI); methanesulfonamide; potassium hexacyanoferrate(III); chiral monocinchona derivative C70H63N5O3; potassium carbonate In water; tert-butyl alcohol at 0℃; for 20h;
Stage #2: 2,2-dimethoxy-propane With toluene-4-sulfonic acid at 23℃; for 1h; Further stages.;
88%
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

(4E,8E,12E)-4,9,13,17-Tetramethyloctadeca-4,8,12,16-tetraen-1-al
56882-09-8

(4E,8E,12E)-4,9,13,17-Tetramethyloctadeca-4,8,12,16-tetraen-1-al

Conditions
ConditionsYield
With periodic acid In tetrahydrofuran; water at 0 - 20℃; for 10h;86%
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With 3-chloro-benzenecarboperoxoic acid In dichloromethane Epoxidation;
Stage #2: With periodic acid Oxidation;
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 2h;
Stage #2: With periodic acid In diethyl ether
3.1 g
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

2,6,10,15,19,23-hexamethyltetracosane-3,7,11,14,18,22-hexaol
57434-13-6

2,6,10,15,19,23-hexamethyltetracosane-3,7,11,14,18,22-hexaol

Conditions
ConditionsYield
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran for 1.33333h;
Stage #2: With dihydrogen peroxide In tetrahydrofuran for 0.5h; Further stages.;
67%
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With borane-THF; 2-methyl-but-2-ene In tetrahydrofuran at 0 - 4℃; for 77h;
Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 20℃; for 12h;
51%
Conditions
ConditionsYield
Stage #1: 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene With N-Bromosuccinimide; water In tetrahydrofuran for 0.75h;
Stage #2: With methanol; potassium carbonate for 0.333333h;
62%
With 3,3-dimethyldioxirane22%
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 1h;14%
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

(3R)-(6E,10E,14E,18E)-2,3-dihydroxy-2,3-dihydrosqualene
63976-65-8

(3R)-(6E,10E,14E,18E)-2,3-dihydroxy-2,3-dihydrosqualene

Conditions
ConditionsYield
With potassium osmate(VI); methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) In water; butan-1-ol at 0℃; for 19h; ligand: 1,4-bisnaphthopyridazine Monomethiodide Salt;62%
With osmium(VIII) oxide; methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) In tert-butyl alcohol at 0℃; for 48h; optical yield given as %ee; enantioselective reaction;12%
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

A

(6E,10E,14E,18E)-3,22-Dichloro-2,6,10,15,19,23-hexamethyl-tetracosa-1,6,10,14,18,23-hexaene

(6E,10E,14E,18E)-3,22-Dichloro-2,6,10,15,19,23-hexamethyl-tetracosa-1,6,10,14,18,23-hexaene

B

(6E,10E,14E,18E)-3-Chloro-2,6,10,15,19,23-hexamethyl-tetracosa-1,6,10,14,18,22-hexaene

(6E,10E,14E,18E)-3-Chloro-2,6,10,15,19,23-hexamethyl-tetracosa-1,6,10,14,18,22-hexaene

Conditions
ConditionsYield
With N-chloro-succinimide; selenenyl bromide In dichloromethane at 20℃; for 8h;A 18%
B 55%
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

squalene monobromohydrin: 3-bromo-2,6,10,15,19,23-hexamethyl-6,10,14,18,22-tetracosapentaen-2-ol (all E)
65746-05-6

squalene monobromohydrin: 3-bromo-2,6,10,15,19,23-hexamethyl-6,10,14,18,22-tetracosapentaen-2-ol (all E)

Conditions
ConditionsYield
With N-Bromosuccinimide; water In tetrahydrofuran at 20℃; for 1h;51%
With N-Bromosuccinimide; water In tetrahydrofuran for 1h; Ambient temperature;35%
With N-Bromosuccinimide In tetrahydrofuran; water 1.) 0 deg C, 30 min; 2.) RT, 1 h;35%
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

2-[5''''-(1-hydroxy-1-methyl-ethyl)-2,5',2''',2''''-tetramethyl-eicosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5-yl]-propan-2-ol

2-[5''''-(1-hydroxy-1-methyl-ethyl)-2,5',2''',2''''-tetramethyl-eicosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5-yl]-propan-2-ol

Conditions
ConditionsYield
With sodium periodate; ruthenium(IV) oxide In water; ethyl acetate; acetonitrile for 0.5h;50%
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

2-[(2S,5S,2'S,5'S,2''S,5''S,2'''S,5'''R,2''''R,5''''S)-5''''-(1-Hydroxy-1-methyl-ethyl)-2,5',2''',2''''-tetramethyl-icosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5-yl]-propan-2-ol

2-[(2S,5S,2'S,5'S,2''S,5''S,2'''S,5'''R,2''''R,5''''S)-5''''-(1-Hydroxy-1-methyl-ethyl)-2,5',2''',2''''-tetramethyl-icosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5-yl]-propan-2-ol

Conditions
ConditionsYield
With sodium periodate; ruthenium(IV) oxide In ethanol; water; acetonitrile at 0℃; for 0.5h;50%
With sodium periodate; ruthenium tetroxide
With sodium periodate; ruthenium tetroxide
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

C21H16BF2N3O2S

C21H16BF2N3O2S

A

C23H20BF2N3O2S

C23H20BF2N3O2S

B

C28H28BF2N3O2S

C28H28BF2N3O2S

C

C47H58BF2N3O2S

C47H58BF2N3O2S

D

C33H36BF2N3O2S

C33H36BF2N3O2S

Conditions
ConditionsYield
With Hoveyda-Grubbs catalyst second generation In dichloromethane at 40℃; for 1h; Cross Metathesis; regioselective reaction;A 45%
B 6.3%
C 20.3%
D 8.5%
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

(3R)-2,3,22,23-tetrahydroxy-2,3,22,23-tetrahydrosqualene

(3R)-2,3,22,23-tetrahydroxy-2,3,22,23-tetrahydrosqualene

Conditions
ConditionsYield
With potassium osmate(VI); methanesulfonamide; potassium hexacyanoferrate(III); chiral monocinchona derivative C70H63N5O3; potassium carbonate In methanol; water; tert-butyl alcohol at 0℃; for 3h;40%
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

A

squalene monobromohydrin: 3-bromo-2,6,10,15,19,23-hexamethyl-6,10,14,18,22-tetracosapentaen-2-ol (all E)
65746-05-6

squalene monobromohydrin: 3-bromo-2,6,10,15,19,23-hexamethyl-6,10,14,18,22-tetracosapentaen-2-ol (all E)

B

squalene dibromohydrin: 3,22-dibromo-2,6,10,15,19,23-hexamethyl-6,10,14,18-tetracosatetraen-2,23-diol (all E)
110390-75-5

squalene dibromohydrin: 3,22-dibromo-2,6,10,15,19,23-hexamethyl-6,10,14,18-tetracosatetraen-2,23-diol (all E)

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrahydrofuran; water 1.) 30 min, 0 deg C; 2.) 1 h, RT;A n/a
B 30%
With N-Bromosuccinimide; water In tetrahydrofuran for 1h; Ambient temperature;A n/a
B 30%
With N-Bromosuccinimide; water In tetrahydrofuran at 0℃; for 1.5h;
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

1-[5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,9,13,17-tetramethyl-octadeca-4,8,12,16-tetraen-1-ol

1-[5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,9,13,17-tetramethyl-octadeca-4,8,12,16-tetraen-1-ol

(4E,8E)-(R)-1-[(2S,5R,2'S,5'R)-5'-(1-Hydroxy-1-methyl-ethyl)-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl]-5,9,13-trimethyl-tetradeca-4,8,12-trien-1-ol

(4E,8E)-(R)-1-[(2S,5R,2'S,5'R)-5'-(1-Hydroxy-1-methyl-ethyl)-5,2'-dimethyl-octahydro-[2,2']bifuranyl-5-yl]-5,9,13-trimethyl-tetradeca-4,8,12-trien-1-ol

(E)-(S)-2-[(2S,5S,2'S,5'R,2''R,5''S)-5''-(1-Hydroxy-1-methyl-ethyl)-2',2''-dimethyl-dodecahydro-[2,2';5',2'']terfuran-5-yl]-6,10-dimethyl-undeca-5,9-dien-2-ol

(E)-(S)-2-[(2S,5S,2'S,5'R,2''R,5''S)-5''-(1-Hydroxy-1-methyl-ethyl)-2',2''-dimethyl-dodecahydro-[2,2';5',2'']terfuran-5-yl]-6,10-dimethyl-undeca-5,9-dien-2-ol

2-[(2S,5S,2'S,5'S,2''S,5''S,2'''S,5'''R,2''''R,5''''S)-5''''-(1-Hydroxy-1-methyl-ethyl)-2,5',2''',2''''-tetramethyl-icosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5-yl]-propan-2-ol

2-[(2S,5S,2'S,5'S,2''S,5''S,2'''S,5'''R,2''''R,5''''S)-5''''-(1-Hydroxy-1-methyl-ethyl)-2,5',2''',2''''-tetramethyl-icosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran-5-yl]-propan-2-ol

Conditions
ConditionsYield
With sodium periodate; ruthenium(IV) oxide In ethanol; water; acetonitrile at 0℃; for 0.0666667h;A 5%
B 4.5%
C 4.3%
D 28%
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

squalene dibromohydrin: 3,22-dibromo-2,6,10,15,19,23-hexamethyl-6,10,14,18-tetracosatetraen-2,23-diol (all E)
110390-75-5

squalene dibromohydrin: 3,22-dibromo-2,6,10,15,19,23-hexamethyl-6,10,14,18-tetracosatetraen-2,23-diol (all E)

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrahydrofuran at 0℃;27%
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one In 1,2-dimethoxyethane; dichloromethane; water Ambient temperature;
With N-Bromosuccinimide; water In tetrahydrofuran
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

(4E, 8E)-5,9,13-trimethyl-4,8,12-tetradecatrienal
67858-78-0

(4E, 8E)-5,9,13-trimethyl-4,8,12-tetradecatrienal

Conditions
ConditionsYield
With MMPP In tetrahydrofuran; water at 25℃; for 48h;26%
Multi-step reaction with 2 steps
1: MCPBA / CH2Cl2 / 0 °C
2: HIO4 / diethyl ether / 25 °C
View Scheme
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

(2E,6E,10E,14E,18E,22E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaenedioic acid
62399-03-5

(2E,6E,10E,14E,18E,22E)-2,6,10,15,19,23-Hexamethyl-tetracosa-2,6,10,14,18,22-hexaenedioic acid

Conditions
ConditionsYield
soil bacterium;26%
2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

A

(2E,6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosadeca-2,6,10,14,18,23-hexaene-1,22-diol

(2E,6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosadeca-2,6,10,14,18,23-hexaene-1,22-diol

B

(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosadeca-1,6,10,14,18,22-hexaen-3-ol
97232-74-1

(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosadeca-1,6,10,14,18,22-hexaen-3-ol

C

(2E,6E,10E,14E,18E,22E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene-1-ol
79370-71-1

(2E,6E,10E,14E,18E,22E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene-1-ol

D

(2E,6E,10E,14E,18E,22E)-2,6,10,15,19,23-hexamethyltetracosadeca-2,6,10,14,18,22-hexaene-1,24-diol
79370-70-0

(2E,6E,10E,14E,18E,22E)-2,6,10,15,19,23-hexamethyltetracosadeca-2,6,10,14,18,22-hexaene-1,24-diol

Conditions
ConditionsYield
Multistep reaction;A 9%
B 26%
C 20%
D 6%

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