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Hangzhou Hysen Pharma co.,Ltd.

We have years of experience to produce Dapagliflozin .We can provide high quality,cheap price,spot supply and good service. If you have any questions,pls do not hesitate to contact us. Hangzhou Hysen pharma CO.,LTD. is a professional Pharmaceutical

Eldecalcitol factory supply

Cas:104121-92-8

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

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Chemvon Biotechnology Co. Ltd.

Eldecalcitolcasno.:104121-92-8 Package:According to your demand Transportation:as requested

Eldecalcitol

Cas:104121-92-8

Min.Order:0 Kilogram

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Type:Lab/Research institutions

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Kono Chem Co.,Ltd

Founded in 2014, Kono Chem Co., Ltd is an export-oriented production enterprise supported by the State Department of Commerce. Kono Chem covers an area of 312,000 square meters, with scientific and technological personnel accounting for more than 35%

Eldecalcitol 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

Cas:104121-92-8

Min.Order:1 Kilogram

FOB Price: $195.0 / 200.0

Type:Other

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Dayang Chem (Hangzhou) Co.,Ltd.

DayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe

Eldecalcitol Manufacturer/High quality/Best price/In stock

Cas:104121-92-8

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

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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

(1α,2β,3β,5Z,7E)-2-(3-Hydroxypropoxy)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol

Cas:104121-92-8

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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Henan Tianfu Chemical Co., Ltd.

Product Name: 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 Synonyms: 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3;Eldecalcitol;ED-71;Eldecalcitol(ED-71);2.beta.-(3-Hydroxypropoxy)-1.alpha.,25-dihydroxyvitaMin D3;(1R,Z)-5-((E)-2-((1R,

104121-92-8 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

Cas:104121-92-8

Min.Order:1 Gram

FOB Price: $8900.0

Type:Lab/Research institutions

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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

New productCAS 104121-92-8 with fast shipping

Cas:104121-92-8

Min.Order:10 Gram

FOB Price: $146.0 / 176.0

Type:Trading Company

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Leader Biochemical Group

About Product Details

China Biggest factory Supply High Quality 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 CAS 104121-92-8

Cas:104121-92-8

Min.Order:1 Gram

FOB Price: $3.0 / 5.0

Type:Lab/Research institutions

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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 We can also provide MT1 peptide powd

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

Cas:104121-92-8

Min.Order:1 Kilogram

FOB Price: $100.0 / 102.0

Type:Trading Company

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Hebei Nengqian Chemical Import and Export Co., LTD

Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

Cas:104121-92-8

Min.Order:1 Kilogram

FOB Price: $9.0 / 99.0

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

9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, 2-(3-hydroxypropoxy)-, (1α,2β,3β,5Z,7E)- 104121-92-8

Cas:104121-92-8

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Qingdao Beluga Import and Export Co., LTD

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 CAS:104121-92-8 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 CAS:104121-92-8

Cas:104121-92-8

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, 2-(3-hydroxypropoxy)-, (1α,2β,3β,5Z,7E)-

Cas:104121-92-8

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

We can provide GMP validation service that complies with SFDA, FDA, WHO and EU EMPA.Excellent registration team could help us easlily to register our products in different countries.If you and your customer are interested in some products or need C

Eldecalcitol manufacturer with low price

Cas:104121-92-8

Min.Order:1 Gram

Negotiable

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

9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, 2-(3-hydroxypropoxy)-, (1α,2β,3β,5Z,7E)-

Cas:104121-92-8

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Triumph International Development Limilted

Triumph has the complete production of G- KG - MT service chain,we can make the new technology into productivity quickly in the research and development of new products. Main Business Custom Synthesis: Trading(Raw Mater

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

Cas:104121-92-8

Min.Order:0 Metric Ton

FOB Price: $18.0 / 20.0

Type:Lab/Research institutions

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Taizhou Crene Biotechnology co.ltd

Our company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-

ED-71 Eldecalcitol 104121-92-8

Cas:104121-92-8

Min.Order:100 Milligram

Negotiable

Type:Lab/Research institutions

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Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

Hot Sale Eldecalcitol,2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 CAS NO.104121-92-8

Cas:104121-92-8

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

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Tianjin Kind Pharma Co., Ltd.

Factory direct sales, accept customization. Eldecalcitol is a derivative of vitamin D3 which is the vitamin that mediates intestinal calcium absorbtion, bone calcium metabolism and probably, muscle activity. Kind Pharma has its own laboratory, we c

eldecalcitol

Cas:104121-92-8

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Afine Chemicals Limited

Company Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments

ELDECALCITOL

Cas:104121-92-8

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Hangzhou Lingrui Chemical Co.,Ltd.

advantage: 1. The best price, satisfactory quality; 2. customers have the right to choose the delivery of parcels (EMS, DHL, FedEx, UPS); 3. customers have the right to choose from the recent effective packaging methods of their products packaging

Best price/In stock Eldecalcitol 104121-92-8

Cas:104121-92-8

Min.Order:1 Gram

Negotiable

Type:Other

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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

9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, 2-(3-hydroxypropoxy)-, (1α,2β,3β,5Z,7E)-

Cas:104121-92-8

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Massive Chemical Technology Co., Ltd.

Massive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

Cas:104121-92-8

Min.Order:1 Gram

FOB Price: $1.0

Type:Lab/Research institutions

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Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

Eldecalcitol

Cas:104121-92-8

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

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Siwei Development Group Ltd.

Product name: Eldecalcitol CAS No.:104121-92-8 Molecule Formula:C30H50O5 Molecule Weight:490.72 Purity: 99.0% Package: 25kg/drum Description:White powder Manufacture Standards:Enterprise Standard TESTING ITEMS SPE

Best Quality Eldecalcitol with good supplier

Cas:104121-92-8

Min.Order:1 Kilogram

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,

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

Cas:104121-92-8

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Xiamen Jenny Chemical Technology Co., Ltd.

GMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,

2-(3-hydroxypropoxy)-1,25-dihydroxyvitaminD3

Cas:104121-92-8

Min.Order:1 Milligram

Negotiable

Type:Trading Company

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EAST CHEMSOURCES LIMITED

factory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B

Hot Sale Eldecalcitol,2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 CAS NO.104121-92-8

Cas:104121-92-8

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

inquiry

Shandong Mopai Biotechnology Co., LTD

Shandong Mopai Biotechnology Co., LTD is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemicals. W

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

Cas:104121-92-8

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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KAISA GROUP INC

1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer

Hot Sale Eldecalcitol,2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 CAS NO.104121-92-8

Cas:104121-92-8

Min.Order:1 Metric Ton

FOB Price: $1.5

Type:Trading Company

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Synthetic route

(1β,2α,3α,5Z,7E)-1,3-bis[(1,1-dimethylethyl)dimethylsilyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-25-trimethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene
342645-84-5

(1β,2α,3α,5Z,7E)-1,3-bis[(1,1-dimethylethyl)dimethylsilyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-25-trimethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With pyridine; hydrogen fluoride In tetrahydrofuran at 20℃;96%
C54H106O5Si4

C54H106O5Si4

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃;89%
((1R,2R,3R,Z)-2-(3-(tert-butyldiphenylsilyloxy)propoxy)-5-((E)-2-((1R,3aS,7aR)-7a-methyl-1-((R)-6-methyl-6-(trimethylsilyloxy)heptan-2-yl)dihydro-1H-indene-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylene cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

((1R,2R,3R,Z)-2-(3-(tert-butyldiphenylsilyloxy)propoxy)-5-((E)-2-((1R,3aS,7aR)-7a-methyl-1-((R)-6-methyl-6-(trimethylsilyloxy)heptan-2-yl)dihydro-1H-indene-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylene cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol; dichloromethane at 20℃; for 5h; Inert atmosphere;80%
C38H66O9

C38H66O9

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With methanol at 20℃; for 66h; Inert atmosphere; stereoselective reaction;68%
(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 96h;61%
(5Z,7E)-(1R,2R,3R)-1,3-bis(tert-butyldimethylsilyloxy)-2-(3-tert-butyldimethylsilyloxypropoxy)-25-triethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene
933779-95-4

(5Z,7E)-(1R,2R,3R)-1,3-bis(tert-butyldimethylsilyloxy)-2-(3-tert-butyldimethylsilyloxypropoxy)-25-triethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 105℃; for 2h;60%
(5R,6R)-6-((R)-1-(methoxymethoxy)allyl)-5-(prop-2-yn-1-yl)-2,4,7,11,13-pentaoxatetradecane

(5R,6R)-6-((R)-1-(methoxymethoxy)allyl)-5-(prop-2-yn-1-yl)-2,4,7,11,13-pentaoxatetradecane

C21H37BrO2

C21H37BrO2

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Stage #1: (5R,6R)-6-((R)-1-(methoxymethoxy)allyl)-5-(prop-2-yn-1-yl)-2,4,7,11,13-pentaoxatetradecane; C21H37BrO2 With tetrakis(triphenylphosphine) palladium(0); triethylamine In toluene at 110℃; for 2h;
Stage #2: With camphor-10-sulfonic acid In methanol at 20℃; for 72h;
36%
25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one
144848-24-8

25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one

[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide
200636-54-0

[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multistep reaction;
methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside
299410-93-8

methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 2.1 g / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C
2.1: 91 percent / BaCO3; NBS / CCl4 / Heating
3.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
4.1: pyridine / 20 °C
5.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
6.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
6.3: 90 percent / K2CO3 / methanol / 20 °C
7.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
8.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
9.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside
299410-95-0

methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 91 percent / BaCO3; NBS / CCl4 / Heating
2.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
3.1: pyridine / 20 °C
4.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
5.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
5.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
5.3: 90 percent / K2CO3 / methanol / 20 °C
6.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
7.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
8.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside
299410-97-2

methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
2.1: pyridine / 20 °C
3.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
4.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
4.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
4.3: 90 percent / K2CO3 / methanol / 20 °C
5.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
6.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
7.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(3R,4S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne
299411-15-7

(3R,4S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
2: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: KOt-Bu / 110 °C
2.1: 2.1 g / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C
3.1: 91 percent / BaCO3; NBS / CCl4 / Heating
4.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
5.1: pyridine / 20 °C
6.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
7.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
7.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
7.3: 90 percent / K2CO3 / methanol / 20 °C
8.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
9.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
10.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(3R,4S,5R)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne-3,5-diol
794516-13-5

(3R,4S,5R)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne-3,5-diol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
2: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
3: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene
794516-11-3

(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
1.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
1.3: 90 percent / K2CO3 / methanol / 20 °C
2.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
3.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
4.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(2R,3S,4R)-4-benzoyloxy-3-[3-(tert-butyldimethylsilyloxy)propoxy]hex-5-ene-1,2-diol
794516-09-9

(2R,3S,4R)-4-benzoyloxy-3-[3-(tert-butyldimethylsilyloxy)propoxy]hex-5-ene-1,2-diol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: pyridine / 20 °C
2.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
3.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
3.3: 90 percent / K2CO3 / methanol / 20 °C
4.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
5.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
6.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
Benzoic acid (1R,2S,3R)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-3-hydroxy-4-(2,4,6-trimethyl-benzenesulfonyloxy)-1-vinyl-butyl ester

Benzoic acid (1R,2S,3R)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-3-hydroxy-4-(2,4,6-trimethyl-benzenesulfonyloxy)-1-vinyl-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
2.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
2.3: 90 percent / K2CO3 / methanol / 20 °C
3.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
4.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
5.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme

Eldecalcitol

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
2.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
3.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
4.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
5.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
6.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
6.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
7.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
(1α,2β,3β,5Z,7E,20S)-1,3-bis[(1,1-dimethylethyl)dimethyl-silyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-9,10-secopregna-5,7,10(19)-triene-20-methyl 4-methylbenzenesulfonate
342645-07-2

(1α,2β,3β,5Z,7E,20S)-1,3-bis[(1,1-dimethylethyl)dimethyl-silyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-9,10-secopregna-5,7,10(19)-triene-20-methyl 4-methylbenzenesulfonate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
1.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
2.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate
66774-80-9

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 97 percent / pyridinium p-toluenesulfonate; pyridinium dichromate / CH2Cl2 / 6 h / 20 °C
2.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
3.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
3.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
4.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: magnesium / tetrahydrofuran / 20 °C / Inert atmosphere
1.2: 18 h / -20 - 0 °C / Inert atmosphere
2.1: tetrabutylammomium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxone / dichloromethane / 6 h / 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
3.2: 4 h / -78 °C / Inert atmosphere
4.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]-1-chloroethane
200636-50-6

[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]-1-chloroethane

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
2.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
3.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
4.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
4.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
5.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 3 steps
2: H2O2
View Scheme
[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide
200636-54-0

[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
2.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
2.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
3.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
{2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-diphenyl-phosphane

{2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-diphenyl-phosphane

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
2.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
3.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
3.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
4.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: H2O2
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethanol
244278-87-3

[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethanol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 83 percent / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
2.1: 82 percent / CSA; (+)-10-camphorsulfonic acid / methanol / 3 h / 20 °C
3.1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C
4.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
5.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
6.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
7.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
8.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
9.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
10.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
11.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
11.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
12.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 14 steps
1.1: pyridine; dmap / dichloromethane / Inert atmosphere
2.1: water; trifluoroacetic acid / dichloromethane / 1 h / -10 °C / Inert atmosphere
3.1: 1H-imidazole / dichloromethane / 11 h / 0 °C / Inert atmosphere
4.1: pyridinium p-toluenesulfonate / dichloromethane / 36 h / 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 70 °C / Inert atmosphere
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / Reflux; Inert atmosphere
7.1: acetic acid; water / tetrahydrofuran / 14 h / 40 °C / Inert atmosphere
8.1: water; tetramethyl ammoniumhydroxide; sodium hydroxide / toluene / 20 h / 20 °C / Inert atmosphere
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
10.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
12.1: lithium hexamethyldisilazane / tetrahydrofuran; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
12.2: 13 h / 20 °C / Inert atmosphere
13.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
13.2: 4 h / -78 °C / Inert atmosphere
14.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,4,5-trihydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate
377091-68-4

[3R-(1Z,3β,4α,5α)]-2-[3,4,5-trihydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C
2.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
3.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
4.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
5.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
6.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
7.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
8.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
9.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
9.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
10.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethyl trimethylacetate
342644-83-1

[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 82 percent / CSA; (+)-10-camphorsulfonic acid / methanol / 3 h / 20 °C
2.1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C
3.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
4.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
5.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
6.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
7.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
8.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
9.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
10.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
10.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
11.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 13 steps
1.1: water; trifluoroacetic acid / dichloromethane / 1 h / -10 °C / Inert atmosphere
2.1: 1H-imidazole / dichloromethane / 11 h / 0 °C / Inert atmosphere
3.1: pyridinium p-toluenesulfonate / dichloromethane / 36 h / 20 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 70 °C / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / Reflux; Inert atmosphere
6.1: acetic acid; water / tetrahydrofuran / 14 h / 40 °C / Inert atmosphere
7.1: water; tetramethyl ammoniumhydroxide; sodium hydroxide / toluene / 20 h / 20 °C / Inert atmosphere
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
9.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
11.1: lithium hexamethyldisilazane / tetrahydrofuran; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
11.2: 13 h / 20 °C / Inert atmosphere
12.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
12.2: 4 h / -78 °C / Inert atmosphere
13.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
(1β,2α,3α,5Z,7E)-1,3-bis[(1,1-dimethylethyl)dimethylsilyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-25-trimethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene
342645-84-5

(1β,2α,3α,5Z,7E)-1,3-bis[(1,1-dimethylethyl)dimethylsilyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-25-trimethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With pyridine; hydrogen fluoride In tetrahydrofuran at 20℃;96%
C54H106O5Si4

C54H106O5Si4

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃;89%
((1R,2R,3R,Z)-2-(3-(tert-butyldiphenylsilyloxy)propoxy)-5-((E)-2-((1R,3aS,7aR)-7a-methyl-1-((R)-6-methyl-6-(trimethylsilyloxy)heptan-2-yl)dihydro-1H-indene-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylene cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

((1R,2R,3R,Z)-2-(3-(tert-butyldiphenylsilyloxy)propoxy)-5-((E)-2-((1R,3aS,7aR)-7a-methyl-1-((R)-6-methyl-6-(trimethylsilyloxy)heptan-2-yl)dihydro-1H-indene-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylene cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol; dichloromethane at 20℃; for 5h; Inert atmosphere;80%
C38H66O9

C38H66O9

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With methanol at 20℃; for 66h; Inert atmosphere; stereoselective reaction;68%
(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 96h;61%
(5Z,7E)-(1R,2R,3R)-1,3-bis(tert-butyldimethylsilyloxy)-2-(3-tert-butyldimethylsilyloxypropoxy)-25-triethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene
933779-95-4

(5Z,7E)-(1R,2R,3R)-1,3-bis(tert-butyldimethylsilyloxy)-2-(3-tert-butyldimethylsilyloxypropoxy)-25-triethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 105℃; for 2h;60%
(5R,6R)-6-((R)-1-(methoxymethoxy)allyl)-5-(prop-2-yn-1-yl)-2,4,7,11,13-pentaoxatetradecane

(5R,6R)-6-((R)-1-(methoxymethoxy)allyl)-5-(prop-2-yn-1-yl)-2,4,7,11,13-pentaoxatetradecane

C21H37BrO2

C21H37BrO2

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Stage #1: (5R,6R)-6-((R)-1-(methoxymethoxy)allyl)-5-(prop-2-yn-1-yl)-2,4,7,11,13-pentaoxatetradecane; C21H37BrO2 With tetrakis(triphenylphosphine) palladium(0); triethylamine In toluene at 110℃; for 2h;
Stage #2: With camphor-10-sulfonic acid In methanol at 20℃; for 72h;
36%
25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one
144848-24-8

25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one

[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide
200636-54-0

[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multistep reaction;
methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside
299410-93-8

methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 2.1 g / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C
2.1: 91 percent / BaCO3; NBS / CCl4 / Heating
3.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
4.1: pyridine / 20 °C
5.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
6.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
6.3: 90 percent / K2CO3 / methanol / 20 °C
7.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
8.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
9.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside
299410-95-0

methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 91 percent / BaCO3; NBS / CCl4 / Heating
2.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
3.1: pyridine / 20 °C
4.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
5.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
5.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
5.3: 90 percent / K2CO3 / methanol / 20 °C
6.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
7.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
8.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside
299410-97-2

methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
2.1: pyridine / 20 °C
3.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
4.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
4.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
4.3: 90 percent / K2CO3 / methanol / 20 °C
5.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
6.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
7.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(3R,4S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne
299411-15-7

(3R,4S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
2: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: KOt-Bu / 110 °C
2.1: 2.1 g / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C
3.1: 91 percent / BaCO3; NBS / CCl4 / Heating
4.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
5.1: pyridine / 20 °C
6.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
7.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
7.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
7.3: 90 percent / K2CO3 / methanol / 20 °C
8.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
9.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
10.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(3R,4S,5R)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne-3,5-diol
794516-13-5

(3R,4S,5R)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne-3,5-diol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
2: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
3: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene
794516-11-3

(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
1.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
1.3: 90 percent / K2CO3 / methanol / 20 °C
2.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
3.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
4.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(2R,3S,4R)-4-benzoyloxy-3-[3-(tert-butyldimethylsilyloxy)propoxy]hex-5-ene-1,2-diol
794516-09-9

(2R,3S,4R)-4-benzoyloxy-3-[3-(tert-butyldimethylsilyloxy)propoxy]hex-5-ene-1,2-diol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: pyridine / 20 °C
2.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
3.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
3.3: 90 percent / K2CO3 / methanol / 20 °C
4.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
5.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
6.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
Benzoic acid (1R,2S,3R)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-3-hydroxy-4-(2,4,6-trimethyl-benzenesulfonyloxy)-1-vinyl-butyl ester

Benzoic acid (1R,2S,3R)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-3-hydroxy-4-(2,4,6-trimethyl-benzenesulfonyloxy)-1-vinyl-butyl ester

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
2.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
2.3: 90 percent / K2CO3 / methanol / 20 °C
3.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
4.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
5.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]ethanol
342644-91-1

[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]ethanol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
2.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
3.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
4.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
5.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
6.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
6.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
7.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
(1α,2β,3β,5Z,7E,20S)-1,3-bis[(1,1-dimethylethyl)dimethyl-silyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-9,10-secopregna-5,7,10(19)-triene-20-methyl 4-methylbenzenesulfonate
342645-07-2

(1α,2β,3β,5Z,7E,20S)-1,3-bis[(1,1-dimethylethyl)dimethyl-silyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-9,10-secopregna-5,7,10(19)-triene-20-methyl 4-methylbenzenesulfonate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
1.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
2.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate
66774-80-9

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 97 percent / pyridinium p-toluenesulfonate; pyridinium dichromate / CH2Cl2 / 6 h / 20 °C
2.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
3.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
3.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
4.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: magnesium / tetrahydrofuran / 20 °C / Inert atmosphere
1.2: 18 h / -20 - 0 °C / Inert atmosphere
2.1: tetrabutylammomium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxone / dichloromethane / 6 h / 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
3.2: 4 h / -78 °C / Inert atmosphere
4.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]-1-chloroethane
200636-50-6

[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]-1-chloroethane

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
2.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
3.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
4.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
4.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
5.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 3 steps
2: H2O2
View Scheme
[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide
200636-54-0

[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
2.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
2.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
3.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
{2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-diphenyl-phosphane

{2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-diphenyl-phosphane

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
2.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
3.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
3.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
4.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: H2O2
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethanol
244278-87-3

[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethanol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 83 percent / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
2.1: 82 percent / CSA; (+)-10-camphorsulfonic acid / methanol / 3 h / 20 °C
3.1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C
4.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
5.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
6.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
7.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
8.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
9.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
10.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
11.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
11.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
12.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 14 steps
1.1: pyridine; dmap / dichloromethane / Inert atmosphere
2.1: water; trifluoroacetic acid / dichloromethane / 1 h / -10 °C / Inert atmosphere
3.1: 1H-imidazole / dichloromethane / 11 h / 0 °C / Inert atmosphere
4.1: pyridinium p-toluenesulfonate / dichloromethane / 36 h / 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 70 °C / Inert atmosphere
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / Reflux; Inert atmosphere
7.1: acetic acid; water / tetrahydrofuran / 14 h / 40 °C / Inert atmosphere
8.1: water; tetramethyl ammoniumhydroxide; sodium hydroxide / toluene / 20 h / 20 °C / Inert atmosphere
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
10.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
12.1: lithium hexamethyldisilazane / tetrahydrofuran; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
12.2: 13 h / 20 °C / Inert atmosphere
13.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
13.2: 4 h / -78 °C / Inert atmosphere
14.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,4,5-trihydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate
377091-68-4

[3R-(1Z,3β,4α,5α)]-2-[3,4,5-trihydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C
2.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
3.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
4.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
5.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
6.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
7.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
8.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
9.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
9.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
10.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethyl trimethylacetate
342644-83-1

[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 82 percent / CSA; (+)-10-camphorsulfonic acid / methanol / 3 h / 20 °C
2.1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C
3.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
4.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
5.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
6.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
7.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
8.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
9.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
10.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
10.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
11.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 13 steps
1.1: water; trifluoroacetic acid / dichloromethane / 1 h / -10 °C / Inert atmosphere
2.1: 1H-imidazole / dichloromethane / 11 h / 0 °C / Inert atmosphere
3.1: pyridinium p-toluenesulfonate / dichloromethane / 36 h / 20 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 70 °C / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / Reflux; Inert atmosphere
6.1: acetic acid; water / tetrahydrofuran / 14 h / 40 °C / Inert atmosphere
7.1: water; tetramethyl ammoniumhydroxide; sodium hydroxide / toluene / 20 h / 20 °C / Inert atmosphere
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
9.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
11.1: lithium hexamethyldisilazane / tetrahydrofuran; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
11.2: 13 h / 20 °C / Inert atmosphere
12.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
12.2: 4 h / -78 °C / Inert atmosphere
13.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate
342644-90-0

[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
2.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
3.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
4.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
5.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
6.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
7.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
8.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
8.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
9.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane / 36 h / 20 °C / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 70 °C / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / Reflux; Inert atmosphere
4.1: acetic acid; water / tetrahydrofuran / 14 h / 40 °C / Inert atmosphere
5.1: water; tetramethyl ammoniumhydroxide; sodium hydroxide / toluene / 20 h / 20 °C / Inert atmosphere
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
7.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
9.1: lithium hexamethyldisilazane / tetrahydrofuran; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
9.2: 13 h / 20 °C / Inert atmosphere
10.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
10.2: 4 h / -78 °C / Inert atmosphere
11.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane
342645-82-3

[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
2.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
3.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
4.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
5.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
5.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
6.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[2-(ethoxycarbonyl)ethoxy]-2-methylenecyclohexylidene]ethyl trimethylacetate
342645-81-2

[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[2-(ethoxycarbonyl)ethoxy]-2-methylenecyclohexylidene]ethyl trimethylacetate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
2.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
3.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
4.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
5.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
6.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
7.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
7.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
8.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
(S)-2-[(1R,3aR,7aR)-octahydro-7a-methyl-4-oxo-4H-inden-1-yl]propyl 4-methylbenzenesulfonate
342645-83-4

(S)-2-[(1R,3aR,7aR)-octahydro-7a-methyl-4-oxo-4H-inden-1-yl]propyl 4-methylbenzenesulfonate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
2.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
2.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
3.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme

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