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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

Mevastatin Manufacturer/High quality/Best price/In stock

Cas:73573-88-3

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

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 Compactin supplier in China

Cas:73573-88-3

Min.Order:1 Metric Ton

Negotiable

Type:Manufacturers

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Hangzhou Dingyan Chem Co., Ltd

Items Standard Result Assay (Ursolic acid) 98%min 98.22% ----------------------------------------------------------------

High purity 73573-88-3 Mevastatin

Cas:73573-88-3

Min.Order:1 Gram

FOB Price: $100.0 / 500.0

Type:Trading Company

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Henan Allgreen Chemical Co.,Ltd

high quality Appearance:White or off-white Solid Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea Port:shanghai

Mevastatin

Cas:73573-88-3

Min.Order:1 Gram

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% Mevastatin 73573-88-3 GMP manufacturer

Cas:73573-88-3

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

Mevastatin

Cas:73573-88-3

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufacturin

Mevastatin

Cas:73573-88-3

Min.Order:1 Kilogram

FOB Price: $1.0 / 10.0

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

New production CAS 73573-88-3 with best quality

Cas:73573-88-3

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Hubei Langyou International Trading Co., Ltd

Advantages: Hubei XinRunde Chemical Co., Ltd is a renowned pharmaceutical manufacturer. We can offer high quality products at competitive price in quick delivery with 100% custom pass guaranteed. Never stop striving to offer our best s

73573-88-3 Mevastatin Manufacturer For Treating Hypercholesterolemia

Cas:73573-88-3

Min.Order:10 Gram

Negotiable

Type:Other

inquiry

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

Mevastatin 73573-88-3

Cas:73573-88-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Leader Biochemical Group

About Product Details Items Specifications Test Results Appearance White to white crystalline powde

Supply High Quality Mevastatin CAS 73573-88-3 For research Use only

Cas:73573-88-3

Min.Order:1 Gram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

inquiry

Baoji Guokang Healthchem co.,ltd

Our company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At present

Mevastatin Adjust blood lipids

Cas:73573-88-3

Min.Order:1 Kilogram

FOB Price: $40.0 / 50.0

Type:Trading Company

inquiry

Qingdao Beluga Import and Export Co., LTD

Mevastatin CAS:73573-88-3 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 high quality organic intermediates

Mevastatin CAS:73573-88-3

Cas:73573-88-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

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

Mevastatin

Cas:73573-88-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

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

Mevastatin

Cas:73573-88-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

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

Mevastatin

Cas:73573-88-3

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

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Afine Chemicals Limited

Our Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter

Mevastatin

Cas:73573-88-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

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

Mevastatin

Cas:73573-88-3

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

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

Mevastatin

Cas:73573-88-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

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

Mevastatin

Cas:73573-88-3

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

Hangzhou Lingrui Chemical Co.,Ltd.

compactinAppearance:white powder Storage:sealed, keep in the ventilated, dry Package:according to customers' requirements Application:health care Transportation:By air(EMS or EUB or FedEx or TNT ect...) or by sea(FOB or CIF or CNF ect...)or according

compactin

Cas:73573-88-3

Min.Order:1 Gram

Negotiable

Type:Other

inquiry

SHANGHAI SYSTEAM BIOCHEM CO., LTD

We are one of a few suppliers that can offer custom synthesis service of this product We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to prov

Mevastatin

Cas:73573-88-3

Min.Order:100 Gram

FOB Price: $100.0 / 2000.0

Type:Lab/Research institutions

inquiry

TaiChem Taizhou Limited

Established in May 2015, TaiChem Ltd. is initially invested by a British research and development company and started by PhDs back from aboard. The company is registered in China Medical City (CMC), Taizhou, Jiangsu Province, and the production site

Mevastatin

Cas:73573-88-3

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Siwei Development Group Ltd.

Product name: Compactin(CAS:73573-88-3) CAS No.:73573-88-3 Molecule Formula:C23H34O5 Molecule Weight:390.52 Purity: 99.0% Package: 25kg/drum Description:White powder Manufacture Standards:Enterprise Standard TESTIN

Best Quality Compactin(CAS:73573-88-3)

Cas:73573-88-3

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

Henan Tianfu Chemical Co., Ltd.

Mevastatin properties Mp 151-153 ° C Specific rotation D22 + 283 ° (c = 0.48 in acetone) Storage conditions 2-8 ° C Solubility DMSO: 20 mg / mL Form powder Color white

Mevastatin, 99%

Cas:73573-88-3

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

inquiry

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 Mevastatin

Cas:73573-88-3

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

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

Mevastatin

Cas:73573-88-3

Min.Order:1 Kilogram

FOB Price: $50.0 / 100.0

Type:Trading Company

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,

Mevastatin

Cas:73573-88-3

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

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

Mevastatin

Cas:73573-88-3

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

inquiry

Synthetic route

(1S,2S,8S,8aR,3'R,5'R,2''S)-methyl 1,2,6,7,8,8a-hexahydro-3',5'-dihydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-1-naphthaleneheptanoate
79814-60-1

(1S,2S,8S,8aR,3'R,5'R,2''S)-methyl 1,2,6,7,8,8a-hexahydro-3',5'-dihydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-1-naphthaleneheptanoate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 1.08333h; Ambient temperature;70%
With toluene-4-sulfonic acid In benzene70%
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
116996-42-0, 117065-49-3

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With Celite; silver carbonate In toluene at 95℃; for 2h;61%
(1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-<2-((2R,4R)-tetrahydro-4-methoxy-6-oxo-2H-pyran-2-yl)-ethyl>-1-naphthyl (2S)-2-methylbutyrate
84751-53-1

(1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-<2-((2R,4R)-tetrahydro-4-methoxy-6-oxo-2H-pyran-2-yl)-ethyl>-1-naphthyl (2S)-2-methylbutyrate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -23℃; for 5h;31%
With boron tribromide In dichloromethane at -23℃; for 6h;31%
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
108713-03-7

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With hydrogen fluoride In water; acetonitrile at 45℃; for 8h;30%
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
87000-71-3

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile at 25℃; for 0.5h; Yield given;
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R,6S)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
116996-42-0, 117065-49-3

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R,6S)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With Celite; silver carbonate In toluene at 95℃; for 2h; Yield given;
3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester
67383-81-7, 79814-60-1, 79896-19-8, 79896-20-1, 79896-21-2, 109785-25-3, 109785-26-4

3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene at 25℃; for 0.5h;
(R)-3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester
67383-81-7, 79814-60-1, 79896-19-8, 79896-20-1, 79896-21-2, 109785-25-3, 109785-26-4

(R)-3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester

A

mevastatin
73573-88-3

mevastatin

B

3,5-bis-epi-compactin
84173-31-9

3,5-bis-epi-compactin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene at 25℃; for 0.25h;A 32 mg
B 22 mg
methyl 3,5-dihydroxy-7-<(1'S,2'S,8'S,8a'S)-2'methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',3',7',8',8a'-hexahydro-1'-naphthyl>heptanoate
67383-81-7, 79814-60-1, 79896-19-8, 79896-20-1, 79896-21-2, 109785-25-3, 109785-26-4

methyl 3,5-dihydroxy-7-<(1'S,2'S,8'S,8a'S)-2'methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',3',7',8',8a'-hexahydro-1'-naphthyl>heptanoate

A

mevastatin
73573-88-3

mevastatin

B

3,5-bis-epi-compactin
84173-31-9

3,5-bis-epi-compactin

Conditions
ConditionsYield
With pyridine hydrogenfluoride In acetonitrile at 0℃; for 6h;A 15.6 mg
B 15.4 mg
(4S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-6-[2-((1S,2S,8aR)-2-methyl-8-triethylsilanyloxy-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-ethyl]-[1,3]dioxane
116996-36-2, 117065-47-1

(4S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-6-[2-((1S,2S,8aR)-2-methyl-8-triethylsilanyloxy-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-ethyl]-[1,3]dioxane

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
2: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
3: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
4: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
5: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
6: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
7: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
8: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 8 steps
1: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
2: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
3: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
4: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
5: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
6: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
7: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
8: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
4-[(1S,5S,6S)-6-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-5-methyl-2-oxo-cyclohex-3-enyl]-4-triethylsilanyloxy-butyraldehyde
116996-35-1, 117065-46-0

4-[(1S,5S,6S)-6-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-5-methyl-2-oxo-cyclohex-3-enyl]-4-triethylsilanyloxy-butyraldehyde

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
2: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
3: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
4: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
5: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
6: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
7: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
8: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
9: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 9 steps
1: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
2: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
3: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
4: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
5: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
6: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
7: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
8: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
9: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(4R,6S)-6-(2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
116996-40-8

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(4R,6S)-6-(2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
2: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
3: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 3 steps
1: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
2: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
3: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(4R,6R)-2,2-dimethyl-6-(2-oxo-ethyl)-[1,3]dioxan-4-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
116996-41-9

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(4R,6R)-2,2-dimethyl-6-(2-oxo-ethyl)-[1,3]dioxan-4-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
2: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 2 steps
1: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
2: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
<4R-<4α*(1R*,2S*)>6α>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-α-(2-methyl-5-oxo-3-cyclohexen-1-yl)-1,3-dioxane-4-propanal
116996-31-7, 126060-10-4

<4R-<4α*(1R*,2S*)>6α>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-α-(2-methyl-5-oxo-3-cyclohexen-1-yl)-1,3-dioxane-4-propanal

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 50 percent / (Ph3P)3RhCl / toluene; acetonitrile / 2.5 h / Heating
2: 1.) LDA / 1.) Et2O, -78 deg C, 1 h; 2.) -78 deg C, 10 min
3: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature
4: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
5: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
6: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
7: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
8: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
9: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
10: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
11: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
12: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
13: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 13 steps
1: 50 percent / (Ph3P)3RhCl / toluene; benzonitrile / 2.5 h / Heating
2: 1.) lithium diisopropylamide (LDA) / 1.) Et2O, -78 deg C, 1 h, 2.) -78 deg C, 10 min
3: 96 percent / i-Pr2NH, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 36 h / Ambient temperature
4: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h
5: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
6: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
7: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
8: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
9: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
10: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
11: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
12: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
13: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one
116996-38-4

(7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
2: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
3: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
4: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
5: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
6: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 6 steps
1: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
2: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
3: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
4: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
5: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
6: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(4S,5S,6S)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-6-(1-hydroxy-pent-4-enyl)-4-methyl-cyclohex-2-enone
116996-33-9, 117065-44-8

(4S,5S,6S)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-6-(1-hydroxy-pent-4-enyl)-4-methyl-cyclohex-2-enone

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature
2: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
3: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
4: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
5: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
6: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
7: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
8: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
9: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
10: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
11: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 11 steps
1: 96 percent / i-Pr2NH, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 36 h / Ambient temperature
2: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h
3: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
4: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
5: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
6: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
7: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
8: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
9: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
10: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
11: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
116996-39-5

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
2: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
3: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
4: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 4 steps
1: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
2: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
3: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
4: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(4S,5S,6S)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-6-(1-triethylsilanyloxy-pent-4-enyl)-cyclohex-2-enone
116996-34-0, 117065-45-9

(4S,5S,6S)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-6-(1-triethylsilanyloxy-pent-4-enyl)-cyclohex-2-enone

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
2: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
3: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
4: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
5: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
6: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
7: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
8: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
9: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
10: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 10 steps
1: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h
2: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
3: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
4: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
5: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
6: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
7: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
8: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
9: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
10: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
<4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one
116996-32-8

<4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 1.) LDA / 1.) Et2O, -78 deg C, 1 h; 2.) -78 deg C, 10 min
2: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature
3: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
4: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
5: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
6: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
7: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
8: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
9: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
10: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
11: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
12: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 12 steps
1: 1.) lithium diisopropylamide (LDA) / 1.) Et2O, -78 deg C, 1 h, 2.) -78 deg C, 10 min
2: 96 percent / i-Pr2NH, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 36 h / Ambient temperature
3: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h
4: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
5: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
6: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
7: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
8: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
9: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
10: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
11: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
12: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol
116996-37-3, 117065-48-2

(7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
2: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
3: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
4: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
5: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
6: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
7: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 7 steps
1: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
2: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
3: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
4: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
5: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
6: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
7: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
<1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol
117065-48-2

<1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
2: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
3: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
4: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
5: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 5 steps
1: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
2: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
3: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
4: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
5: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(R)-3-<(tert-butyldimethylsilyl)oxy>-6-(dimethoxyphosphinyl)-5-oxohexanoic acid
96555-55-4

(R)-3-<(tert-butyldimethylsilyl)oxy>-6-(dimethoxyphosphinyl)-5-oxohexanoic acid

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 92 percent / diethyl ether / 0.25 h / Ambient temperature
2: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
3: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
4: aq. HF / acetonitrile / 0.83 h / Ambient temperature
5: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
6: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
2: LiCl/DBU / acetonitrile
3: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
4: HF / acetonitrile
5: NaBH4 / 0.5 h / -15 °C
6: 70 percent / p-TsOH / benzene
View Scheme
(R)-6-(Dimethoxyphosphinyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxohexanoic acid, methylester
96555-58-7

(R)-6-(Dimethoxyphosphinyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxohexanoic acid, methylester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
2: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
3: aq. HF / acetonitrile / 0.83 h / Ambient temperature
4: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
5: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: LiCl/DBU / acetonitrile
2: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
3: HF / acetonitrile
4: NaBH4 / 0.5 h / -15 °C
5: 70 percent / p-TsOH / benzene
View Scheme
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-formyl-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
96575-19-8

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-formyl-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
2: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
3: aq. HF / acetonitrile / 0.83 h / Ambient temperature
4: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
5: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: LiCl/DBU / acetonitrile
2: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
3: HF / acetonitrile
4: NaBH4 / 0.5 h / -15 °C
5: 70 percent / p-TsOH / benzene
View Scheme
(3R,1'R)-methyl 1'-phenylethyl 3-hydroxypentanedioate
96575-20-1

(3R,1'R)-methyl 1'-phenylethyl 3-hydroxypentanedioate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 1.) N-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT
2: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature
3: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature
4: 92 percent / diethyl ether / 0.25 h / Ambient temperature
5: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
6: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
7: aq. HF / acetonitrile / 0.83 h / Ambient temperature
8: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
9: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 9 steps
1: 43 percent / tetrahydrofuran / 0.17 h / -78 °C
2: C3H4N2
3: H2 / Pd-C
5: LiCl/DBU / acetonitrile
6: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
7: HF / acetonitrile
8: NaBH4 / 0.5 h / -15 °C
9: 70 percent / p-TsOH / benzene
View Scheme
(3R,1'R)-methyl 1'-phenylethyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate
96555-51-0

(3R,1'R)-methyl 1'-phenylethyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 99 percent / aq. HF / acetonitrile / 1.25 h / Ambient temperature
2: 1.) N-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT
3: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature
4: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature
5: 92 percent / diethyl ether / 0.25 h / Ambient temperature
6: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
7: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
8: aq. HF / acetonitrile / 0.83 h / Ambient temperature
9: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
10: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 10 steps
1: HF / acetonitrile
2: 43 percent / tetrahydrofuran / 0.17 h / -78 °C
3: C3H4N2
4: H2 / Pd-C
6: LiCl/DBU / acetonitrile
7: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
8: HF / acetonitrile
9: NaBH4 / 0.5 h / -15 °C
10: 70 percent / p-TsOH / benzene
View Scheme
(R)-dimethyl <<4-<<(R)-phenylethoxy>carbonyl>-3-hydroxybutyryl>methyl>phosphonate
96555-53-2

(R)-dimethyl <<4-<<(R)-phenylethoxy>carbonyl>-3-hydroxybutyryl>methyl>phosphonate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature
2: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature
3: 92 percent / diethyl ether / 0.25 h / Ambient temperature
4: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
5: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
6: aq. HF / acetonitrile / 0.83 h / Ambient temperature
7: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
8: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 8 steps
1: C3H4N2
2: H2 / Pd-C
4: LiCl/DBU / acetonitrile
5: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
6: HF / acetonitrile
7: NaBH4 / 0.5 h / -15 °C
8: 70 percent / p-TsOH / benzene
View Scheme
(R)-dimethyl <<3-<(tert-butyldimethylsilyl)oxy>-4-<<(R)-phenylethoxy>carbonyl>butyryl>methyl>phosphonate
96555-54-3

(R)-dimethyl <<3-<(tert-butyldimethylsilyl)oxy>-4-<<(R)-phenylethoxy>carbonyl>butyryl>methyl>phosphonate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature
2: 92 percent / diethyl ether / 0.25 h / Ambient temperature
3: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
4: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
5: aq. HF / acetonitrile / 0.83 h / Ambient temperature
6: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
7: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 7 steps
1: H2 / Pd-C
3: LiCl/DBU / acetonitrile
4: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
5: HF / acetonitrile
6: NaBH4 / 0.5 h / -15 °C
7: 70 percent / p-TsOH / benzene
View Scheme
(1S,2S,8S,8aR,5'R,2''S)-methyl 1,2,6,7,8,8a-hexahydro-5'hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthaleneheptanoate
96555-61-2

(1S,2S,8S,8aR,5'R,2''S)-methyl 1,2,6,7,8,8a-hexahydro-5'hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthaleneheptanoate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
2: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: NaBH4 / 0.5 h / -15 °C
2: 70 percent / p-TsOH / benzene
View Scheme
mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
85.4%
Product distribution / selectivity;
mevastatin
73573-88-3

mevastatin

<1S-<1α(3R*,5S*),2α,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2-methyl-1-naphthalenyl)-1,3,5-heptanetriol
161466-60-0

<1S-<1α(3R*,5S*),2α,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2-methyl-1-naphthalenyl)-1,3,5-heptanetriol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 9h; Ambient temperature;81%
With lithium aluminium tetrahydride In diethyl ether
mevastatin
73573-88-3

mevastatin

6-desmethylmonacolin J
58889-19-3

6-desmethylmonacolin J

Conditions
ConditionsYield
With lithium hydroxide for 24h; Heating;75%
Multi-step reaction with 2 steps
1: aq. LiOH / 24 h / Heating
2: 30 mg / toluene / 1 h / Heating
View Scheme
mevastatin
73573-88-3

mevastatin

(1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-<2-((2R,4R)-tetrahydro-4-methoxy-6-oxo-2H-pyran-2-yl)-ethyl>-1-naphthyl (2S)-2-methylbutyrate
84751-53-1

(1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-<2-((2R,4R)-tetrahydro-4-methoxy-6-oxo-2H-pyran-2-yl)-ethyl>-1-naphthyl (2S)-2-methylbutyrate

Conditions
ConditionsYield
In diethyl ether; water at 0℃;38%
formic acid
64-18-6

formic acid

mevastatin
73573-88-3

mevastatin

(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-18-6

(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

Conditions
ConditionsYield
With tert-butylhypochlorite In dichloromethane at -10℃; Product distribution; Mechanism; reactions 1 or 2 equiv. terc-BuOCl;
With tert-butylhypochlorite In dichloromethane at -10℃;
formic acid
64-18-6

formic acid

mevastatin
73573-88-3

mevastatin

(S)-2-Methyl-butyric acid (1S,4S,5R,6S,7R,8S)-4,5-dichloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-1-yl ester

(S)-2-Methyl-butyric acid (1S,4S,5R,6S,7R,8S)-4,5-dichloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-1-yl ester

Conditions
ConditionsYield
With tert-butylhypochlorite In dichloromethane at -10℃;
mevastatin
73573-88-3

mevastatin

anhydrocompactin
84173-32-0

anhydrocompactin

Conditions
ConditionsYield
With potassium hydrogensulfate In N,N-dimethyl-formamide for 6h; Heating;2.7 mg
tert-butoxy radical
3141-58-0

tert-butoxy radical

mevastatin
73573-88-3

mevastatin

A

acetone
67-64-1

acetone

B

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Conditions
ConditionsYield
In acetonitrile at 40℃; for 15h; Kinetics; Product distribution;
mevastatin
73573-88-3

mevastatin

(3R,5R)-3,5-Dihydroxy-7-((1S,2S,8S,8aR)-8-hydroxy-2-methyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-heptanoic acid

(3R,5R)-3,5-Dihydroxy-7-((1S,2S,8S,8aR)-8-hydroxy-2-methyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-heptanoic acid

Conditions
ConditionsYield
With lithium hydroxide for 24h; Heating;
ethanol
64-17-5

ethanol

mevastatin
73573-88-3

mevastatin

3,5-dihydroxy-7-[2-methyl-8-(2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid ethyl ester

3,5-dihydroxy-7-[2-methyl-8-(2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid ethyl ester

Conditions
ConditionsYield
With potassium hydroxide
mevastatin
73573-88-3

mevastatin

(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-18-6

(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Acetic acid (1S,7S,8S,8aR)-7-methyl-8-((3R,5S)-3,5,7-triacetoxy-heptyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Acetic acid (1S,7S,8S,8aR)-7-methyl-8-((3R,5S)-3,5,7-triacetoxy-heptyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4 / diethyl ether
2: pyridine, DMAP
View Scheme
mevastatin
73573-88-3

mevastatin

<4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one
116996-32-8

<4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 79 percent / LDA, Et3N / 0.42 h / -78 °C
10: 1.) m-CPBA, 2.) Bu4NF, AcOH
11: AcOH / methanol / 11 h
12: PPTS / 7.5 h
13: aq. NaIO4 / methanol / 23 h / Ambient temperature
14: PPTS / 2.5 h
View Scheme
Multi-step reaction with 13 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min
10: AcOH / methanol / 11 h
11: PPTS / 7.5 h
12: aq. NaIO4 / methanol / 23 h / Ambient temperature
13: PPTS / 2.5 h
View Scheme
mevastatin
73573-88-3

mevastatin

<1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol
117065-48-2

<1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
View Scheme
mevastatin
73573-88-3

mevastatin

(4R,5R)-5-[(3R,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-4-methyl-cyclohex-2-enone

(4R,5R)-5-[(3R,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-4-methyl-cyclohex-2-enone

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 79 percent / LDA, Et3N / 0.42 h / -78 °C
10: 1.) m-CPBA, 2.) Bu4NF, AcOH
11: AcOH / methanol / 11 h
12: PPTS / 7.5 h
13: aq. NaIO4 / methanol / 23 h / Ambient temperature
View Scheme
Multi-step reaction with 12 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min
10: AcOH / methanol / 11 h
11: PPTS / 7.5 h
12: aq. NaIO4 / methanol / 23 h / Ambient temperature
View Scheme
mevastatin
73573-88-3

mevastatin

<1S-<1α(3R*,5S*),2α,8β,8aα>>-1<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-7-(1,2,6,7,8,8a-hexahydro-8-hydroxy-2-methyl-1-naphthalenyl)-3,5-heptanediol
126060-27-3

<1S-<1α(3R*,5S*),2α,8β,8aα>>-1<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-7-(1,2,6,7,8,8a-hexahydro-8-hydroxy-2-methyl-1-naphthalenyl)-3,5-heptanediol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
View Scheme
mevastatin
73573-88-3

mevastatin

<1aR-<1aα,4β,4aα,5α(4R*,6S*),6α>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1a,2,4,4a,5,6-hexahydro-6-methyl-3H-naphth<1,8a-b>oxiren-4-ol
161466-61-1

<1aR-<1aα,4β,4aα,5α(4R*,6S*),6α>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1a,2,4,4a,5,6-hexahydro-6-methyl-3H-naphth<1,8a-b>oxiren-4-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
View Scheme
mevastatin
73573-88-3

mevastatin

(4R,7S,8S,8aR)-8-[(3R,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-2,4,4a-trihydroxy-7-methyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one

(4R,7S,8S,8aR)-8-[(3R,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-2,4,4a-trihydroxy-7-methyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 79 percent / LDA, Et3N / 0.42 h / -78 °C
10: 1.) m-CPBA, 2.) Bu4NF, AcOH
11: AcOH / methanol / 11 h
View Scheme
Multi-step reaction with 10 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min
10: AcOH / methanol / 11 h
View Scheme
mevastatin
73573-88-3

mevastatin

<4R-<4α,7β,8β(4R*,6S*),8aβ>>-4-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-3,4,4a,7,8,8a-hexahydro-2,4,4a-trihydroxy-7-methyl-1(2H)naphthalenone

<4R-<4α,7β,8β(4R*,6S*),8aβ>>-4-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-3,4,4a,7,8,8a-hexahydro-2,4,4a-trihydroxy-7-methyl-1(2H)naphthalenone

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 79 percent / LDA, Et3N / 0.42 h / -78 °C
10: 1.) m-CPBA, 2.) Bu4NF, AcOH
11: AcOH / methanol / 11 h
12: PPTS / 7.5 h
View Scheme
Multi-step reaction with 11 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min
10: AcOH / methanol / 11 h
11: PPTS / 7.5 h
View Scheme

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