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Xi'an Quanao Biotech Co., Ltd.

High Quality 100% Natural halal kosher certificate Red Yeast Rice Extract Powder 5% Lovastatin Xi'an Quanao Biotech Co., Ltd. is is a global chemical industry manufacturers and suppliers of pharmaceuticals and intermediates, peptide,Nootropis

High Quality 100% Natural halal kosher certificate Red Yeast Rice Extract Powder 5% Lovastatin

Cas:75330-75-5

Min.Order:1 Kilogram

FOB Price: $55.0 / 70.0

Type:Manufacturers

inquiry

Dayang Chem (Hangzhou) Co.,Ltd.

Dayangchem's 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. DayangChem can provide different quantities

Lovastatin Manufacturer/High quality/Best price/In stock

Cas:75330-75-5

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Sinoway Industrial Co., Ltd.

Why is SINOWAY: 1) Specialized in pharmaceutical and healthcare industrial since 1987. 2) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days. 4) We have warehouse in USA with quickly shipment . 5) We can

10:1 & 0.5%-3% lovastatin Red Yeast Rice Extract 3% Monacolin K

Cas:75330-75-5

Min.Order:25 Kilogram

Negotiable

Type:Trading Company

inquiry

Hangzhou Dingyan Chem Co., Ltd

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

High purity 75330-75-5 Lovastatin

Cas:75330-75-5

Min.Order:1 Gram

FOB Price: $100.0 / 500.0

Type:Trading Company

inquiry

Kono Chem Co.,Ltd

Superiority kono chem is a leading manufacturer and supplier of chemicals in China. We develop ,produce and distribute high quality pharmaceuticals, intermediates, special chemicals and other fine chemicals. We could give you: 1.Best

Lovastatin red yeast rice extractwith best price and top quality

Cas:75330-75-5

Min.Order:1 Kilogram

FOB Price: $800.0 / 1000.0

Type:Other

inquiry

Wuhan Fortuna Chemical Co.,Ltd

Unique advantages of Lovastatin Cas 75330-75-5 Guaranteed purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:White to off-white crystalline powder Storage:Cool dry place Package:25kg/d

Hot selling high quality Lovastatin Cas 75330-75-5 with favorable price and good service

Cas:75330-75-5

Min.Order:25 Kilogram

Negotiable

Type:Trading Company

inquiry

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

Factory Price API 99% Lovastatin 75330-75-5 GMP Manufacturer

Cas:75330-75-5

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

inquiry

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

Lovastatin

Cas:75330-75-5

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Hebei yanxi chemical co.,LTD.

CAS: 842212-02-1 Molecular weight: 197.661 Compound purity: > 99.7% Related substance: Total Impurities(%) ≤ 0.3% Appearance: Crystals IUPAC:1-(4-Chlorophenyl)-2-(methylamino)propan-1-one

lovastatin

Cas:75330-75-5

Min.Order:1 Gram

FOB Price: $1000.0

Type:Trading Company

inquiry

Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 11 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.

Butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrah 75330-75-5

Cas:75330-75-5

Min.Order:100 Gram

FOB Price: $200.0

Type:Lab/Research institutions

inquiry

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

Lovastatin

Cas:75330-75-5

Min.Order:1 Kilogram

FOB Price: $9.0 / 99.0

Type:Trading Company

inquiry

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 75330-75-5 with best quality

Cas:75330-75-5

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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

Lovastatin

Cas:75330-75-5

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

inquiry

Henan Sinotech Import&Export Corporation

Production name Lovastatin CAS No. 75330-75-5 Appearance White powder Molecular Formula C24H36O5 Molecular Weight 404.540 Assay 99% Appearance:White powder Storage:Store

Lovastatin CAS:75330-75-5

Cas:75330-75-5

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

inquiry

Hubei Langyou International Trading Co., Ltd

1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:White Crystalline Powder Storage:Store in sealed conta

high quality 75330-75-5 Lovastatin with best price

Cas:75330-75-5

Min.Order:10 Gram

Negotiable

Type:Other

inquiry

HANWAYS CHEMPHARM CO.,LIMITED

We are concentrating on APIs and pharmaceutical intermediates. With in depth knowledge and understanding in this industry, we are indulged in supplying a wide assortments of Lovastatin from Wuhan, Hubei, China. It is ma

Lovastatin

Cas:75330-75-5

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Trading Company

inquiry

Shanghai Upbio Tech Co.,Ltd

1,In No Less five years exporting experience. 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Onchem specialized in APIs, chemical intermediate

Topsale Lovastatin 99% with lower price

Cas:75330-75-5

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

Xi'an Faithful Biotech Co., Ltd.

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

Fast Delivery Raw monacolin k /Lovastatin /SiMvastatin EP IMpurity E White Powder

Cas:75330-75-5

Min.Order:10 Gram

FOB Price: $3.5

Type:Trading Company

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 prese

Lovastatin 99%

Cas:75330-75-5

Min.Order:1 Kilogram

FOB Price: $75.0 / 89.0

Type:Trading Company

inquiry

Qingdao Beluga Import and Export Co., LTD

Lovastatin CAS:75330-75-5 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,

Lovastatin CAS:75330-75-5

Cas:75330-75-5

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

Changchun Artel lmport and Export trade company

Product Detail Minimum Order Qty. 10 Gram Supply Ability 500 Kilograms/Month Storage store in cool, dry, ventilated place 20℃ Delivery Time 3 business days after payment Payment Term TT,western union,Paypal,

Lovastatin CAS NO.: 75330-75-5

Cas:75330-75-5

Min.Order:20 Metric Ton

Negotiable

Type:Trading Company

inquiry

Hubei Jiutian Bio-medical Technology Co., Ltd

1,we produce and sell good chemicals around the world. 2,our success rate is about 95%. this means, if customer order is accepted, the probability that the customer will obtain the ordered substances, is 95%. 3,our staff consists of highly qualifie

Lovastatin CAS 75330-75-5

Cas:75330-75-5

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

CAS NO.:75330-75-5

Cas:75330-75-5

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

Product name : Lovastatin CAS : 75330-75-5 Standard : USP Stock : Fresh Package:25kg net per drum Application:Lovastatin (mevinolin) is a metabolite first isolated from Monascus ruber and later found in several other fungal species. Lov

Lovastatin

Cas:75330-75-5

Min.Order:1 Gram

Negotiable

Type:Trading Company

inquiry

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 Service 1.Own made fine chemical products 2.Out sourcing and quality c

Lovastatin

Cas:75330-75-5

Min.Order:100 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

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

high purity Lovastatin cas no.75330-75-5

Cas:75330-75-5

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Hubei Yuanmeng Biological Technology Co., Ltd.

Hubei Yuanmeng Biological Technology Co., Ltd., which is located in Wuhan, China. We are specializing in the exportation of APIs, and plant extracts ect. Our products has been exported to America, Australia, Brazil, the Europe, Middle East and other

High Purity Lovastatin CAS 75330-75-5 with Fast Shipment

Cas:75330-75-5

Min.Order:1 Kilogram

FOB Price: $3.0 / 5.0

Type:Trading Company

inquiry

Nanjing Fred Technology Co.,Ltd.

Lovastatin is one of the most competitive products in our company, we can supply it with good quality and best price. Appearance:White to off-white solid Storage:Room temperature, Keep in Dark Place. Package:According to the demand of customer Applic

Lovastatin

Cas:75330-75-5

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

6(R)-<2-<1,2,6,7,8,8a(R)-Hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutyryl>oxy>-1(S)-naphtyl>ethyl>-3,4,5,6-tetrahydro-4(R)-<(tert-butyldimethylsilyl)oxy>-2H-pyran-2-one
79691-11-5

6(R)-<2-<1,2,6,7,8,8a(R)-Hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutyryl>oxy>-1(S)-naphtyl>ethyl>-3,4,5,6-tetrahydro-4(R)-<(tert-butyldimethylsilyl)oxy>-2H-pyran-2-one

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile at 25℃; for 1.4h;94%
With hydrogen fluoride In acetonitrile at 0℃; for 5h;77%
With tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran
With tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran for 18h; Ambient temperature;
ammonium mevinolinic acid

ammonium mevinolinic acid

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Stage #1: ammonium mevinolinic acid With phosphoric acid In toluene; butanone at 20 - 82℃; for 2 - 2.5h;
Stage #2: With triethylamine In water; toluene; butanone at 20℃;
78.2%
With sulfuric acid In acetonitrile at -22 - -17℃; for 0.5h;
Conditions
ConditionsYield
With Celite; silver carbonate In toluene at 85 - 95℃; for 1h;77%
With Celite; toluene; silver carbonate In toluene at 90℃; for 1h;77%
lovastatin acid
75225-51-3, 137767-34-1

lovastatin acid

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
With phosphoric acid In water; toluene at 20 - 55℃; for 19h; pH=3.5; Product distribution / selectivity;76.12%
With trifluoroacetic acid In ethyl acetate for 0.166667h;
(S)-2-Methyl-butyric acid (1S,3S,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
85614-12-6

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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
2: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
3: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
(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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: imidazole / acetonitrile / 25 °C
2: Ti(OiPr)4 / propan-2-ol / 0.5 h / 60 °C
3: 92 percent / PDC / toluene / 0.33 h / 80 °C
4: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C
5: 65 percent / tetrahydrofuran / -78 °C
6: H+ / CHCl3
7: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
8: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
9: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
2-methyl-butyric acid 8-{2-[4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-6-oxo-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl ester
153079-17-5

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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 65 percent / tetrahydrofuran / -78 °C
2: H+ / CHCl3
3: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
4: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
5: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-6-hydroxy-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-20-0

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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 92 percent / PDC / toluene / 0.33 h / 80 °C
2: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C
3: 65 percent / tetrahydrofuran / -78 °C
4: H+ / CHCl3
5: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
6: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
7: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,3R,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-oxo-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-22-2

(S)-2-Methyl-butyric acid (1S,3R,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-oxo-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H+ / CHCl3
2: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
3: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
4: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,4S,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-7-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-21-1

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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C
2: 65 percent / tetrahydrofuran / -78 °C
3: H+ / CHCl3
4: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
5: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
6: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-6-formyloxy-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-19-7

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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: Ti(OiPr)4 / propan-2-ol / 0.5 h / 60 °C
2: 92 percent / PDC / toluene / 0.33 h / 80 °C
3: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C
4: 65 percent / tetrahydrofuran / -78 °C
5: H+ / CHCl3
6: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
7: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
8: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,3R,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-trifluoromethanesulfonyloxy-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
153079-24-4

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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
2: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme
<1S-<1α(R*),3α,7β,8β(4S*,6R*),8aβ>>-1,2,3,7,8,8a-hexahydro-8-<2-<6-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-3,7-dimethyl-1-naphthalenyl 2-methylbutanoate
116996-47-5

<1S-<1α(R*),3α,7β,8β(4S*,6R*),8aβ>>-1,2,3,7,8,8a-hexahydro-8-<2-<6-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-3,7-dimethyl-1-naphthalenyl 2-methylbutanoate

lovastatin
75330-75-5

lovastatin

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., 20 min
2: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
3: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 3 steps
1: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
2: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
3: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<1S-<1α(R*),3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<2,2-dimethyl-6-(2-oxoethyl)-1,3-dioxan-4-yl>ethyl>-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl 2-methylbutanoate
116996-48-6

<1S-<1α(R*),3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<2,2-dimethyl-6-(2-oxoethyl)-1,3-dioxan-4-yl>ethyl>-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl 2-methylbutanoate

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
2: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 2 steps
1: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
2: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 50 percent / (Ph3P)3RhCl / toluene; acetonitrile / 2.5 h / Heating
2: 1.) LDA / 1.)Et2O, -78 deg C, 45 min; 2.) -78 deg C, 10 min
3: 85 percent / i-Pr2NH / DMAP / diethyl ether / 24 h / Ambient temperature
4: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C -> r.t., 3 h
5: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 4 h
6: 1.) Bu4NF ; 2.) t-BuPh2SiCl, Et3N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH2Cl2, r.t., 24 h
7: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
8: 95 percent / Bu4NF / tetrahydrofuran / 3 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., 20 min
10: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
11: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 12 steps
1: 50 percent / (Ph3P)3RhCl / toluene; benzonitrile / 2.5 h / Heating
2: 1.) lithium diisopropylamide (LDA) / 1.) ether, -78 deg C, 45 min, 2.) -78 deg C, 10 min
3: 85 percent / diisopropylamine, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 24 h / Ambient temperature
4: 85 percent / 1.) O3, 2.) triphenylphosphine / CH2Cl2 / 1.) -78 deg C, 5 min, 2.) 3 h
5: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 4 h
6: 99 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 22 h / Ambient temperature
7: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
8: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
9: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
10: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
11: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
12: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<1S-<1α,3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenol
116996-45-3

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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
2: 95 percent / Bu4NF / tetrahydrofuran / 3 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., 20 min
4: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
5: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 5 steps
1: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
2: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
3: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
4: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
5: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<4S-<4α,5α(4S*,4S*),6β(1R*,3S*)>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-6-(1-hydroxy-3-methyl-4-pentenyl)-4-methyl-2-cyclohexen-1-one
117020-88-9

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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 85 percent / i-Pr2NH / DMAP / diethyl ether / 24 h / Ambient temperature
2: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C -> r.t., 3 h
3: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 4 h
4: 1.) Bu4NF ; 2.) t-BuPh2SiCl, Et3N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH2Cl2, r.t., 24 h
5: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
6: 95 percent / Bu4NF / tetrahydrofuran / 3 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., 20 min
8: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
9: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 10 steps
1: 85 percent / diisopropylamine, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 24 h / Ambient temperature
2: 85 percent / 1.) O3, 2.) triphenylphosphine / CH2Cl2 / 1.) -78 deg C, 5 min, 2.) 3 h
3: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 4 h
4: 99 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 22 h / Ambient temperature
5: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
6: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
7: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
8: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
9: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
10: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<1S-<1α,3α,7β,8β(4Σ*,6R*)8aβ>>-<<8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl>oxy>triethylsilane
116996-44-2

<1S-<1α,3α,7β,8β(4Σ*,6R*)8aβ>>-<<8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl>oxy>triethylsilane

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) Bu4NF ; 2.) t-BuPh2SiCl, Et3N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH2Cl2, r.t., 24 h
2: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
3: 95 percent / Bu4NF / tetrahydrofuran / 3 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., 20 min
5: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
6: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 7 steps
1: 99 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 22 h / Ambient temperature
2: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
3: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
4: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
5: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
6: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
7: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<1S-<1α(R*),3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl 2-methylbutanoate
116996-46-4

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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / Bu4NF / tetrahydrofuran / 3 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., 20 min
3: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
4: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 4 steps
1: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
2: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
3: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
4: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<4S-<4α,5α(4S*,6R*),6β(1R*,3S*)>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-6-<3-methyl-1-<(triethylsilyl)oxy>-4-pentenyl>-2-cyclohexen-1-one
117020-89-0

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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C -> r.t., 3 h
2: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 4 h
3: 1.) Bu4NF ; 2.) t-BuPh2SiCl, Et3N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH2Cl2, r.t., 24 h
4: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
5: 95 percent / Bu4NF / tetrahydrofuran / 3 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., 20 min
7: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
8: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 9 steps
1: 85 percent / 1.) O3, 2.) triphenylphosphine / CH2Cl2 / 1.) -78 deg C, 5 min, 2.) 3 h
2: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 4 h
3: 99 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 22 h / Ambient temperature
4: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
5: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
6: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
7: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
8: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
9: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
<1S-<1α(αS,γR*),5β,6β(4Σ*,6R*)>>-6-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-α,5-dimethyl-2-oxo-γ-<(triethylsilyl)oxy>-3-cyclohexene-1-butanal
116996-43-1

<1S-<1α(αS,γR*),5β,6β(4Σ*,6R*)>>-6-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-α,5-dimethyl-2-oxo-γ-<(triethylsilyl)oxy>-3-cyclohexene-1-butanal

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 4 h
2: 1.) Bu4NF ; 2.) t-BuPh2SiCl, Et3N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH2Cl2, r.t., 24 h
3: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
4: 95 percent / Bu4NF / tetrahydrofuran / 3 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., 20 min
6: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
7: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 8 steps
1: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 4 h
2: 99 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 22 h / Ambient temperature
3: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
4: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
5: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
6: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
7: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
8: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1.) LDA / 1.)Et2O, -78 deg C, 45 min; 2.) -78 deg C, 10 min
2: 85 percent / i-Pr2NH / DMAP / diethyl ether / 24 h / Ambient temperature
3: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C -> r.t., 3 h
4: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 4 h
5: 1.) Bu4NF ; 2.) t-BuPh2SiCl, Et3N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH2Cl2, r.t., 24 h
6: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
7: 95 percent / Bu4NF / tetrahydrofuran / 3 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., 20 min
9: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
10: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
Multi-step reaction with 11 steps
1: 1.) lithium diisopropylamide (LDA) / 1.) ether, -78 deg C, 45 min, 2.) -78 deg C, 10 min
2: 85 percent / diisopropylamine, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 24 h / Ambient temperature
3: 85 percent / 1.) O3, 2.) triphenylphosphine / CH2Cl2 / 1.) -78 deg C, 5 min, 2.) 3 h
4: 86 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 4 h
5: 99 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 22 h / Ambient temperature
6: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
7: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
8: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
9: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
10: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
11: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
(S)-2-methylbutyric anhydride
84131-91-9

(S)-2-methylbutyric anhydride

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 97 percent / Et3N / DMAP / CH2Cl2 / 88 h / Ambient temperature
2: 95 percent / Bu4NF / tetrahydrofuran / 3 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., 20 min
4: 97 percent / 1.3N HCl / tetrahydrofuran / 4 h / Ambient temperature
5: 77 percent / Ag2CO3/Celite, PhMe / toluene / 1 h / 90 °C
View Scheme
(S)-2-methylbutanoyl chloride
27763-54-8

(S)-2-methylbutanoyl chloride

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4-(dimethylamino)pyridine (DMAP), pyridine / 1.) 0 deg C, 1 h, 2.) RT, 18 h
2: acetic acid, Bu4NF*3H2O / tetrahydrofuran / 18 h / Ambient temperature
View Scheme
(4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one
79902-31-1

(4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4-(dimethylamino)pyridine (DMAP), pyridine / 1.) 0 deg C, 1 h, 2.) RT, 18 h
2: acetic acid, Bu4NF*3H2O / tetrahydrofuran / 18 h / Ambient temperature
View Scheme
(1S,3R,7S,8S,8aR)-8-{2-[(4R,6S)-6-(2-Hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol
125975-03-3

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

lovastatin
75330-75-5

lovastatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 24 h / Ambient temperature
2: 91 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 72 h / Ambient temperature
3: 95 percent / 1.1 M Bu4N(1+)*F(1-) / tetrahydrofuran / 3 h / Ambient temperature
4: 97 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
5: 97 percent / 10percent aq. HCl / tetrahydrofuran / 4 h / Ambient temperature
6: 77 percent / Ag2CO3/Celite / toluene / 1 h / 85 - 95 °C
View Scheme
lovastatin
75330-75-5

lovastatin

α,β-dehydrolovastatin
109273-98-5

α,β-dehydrolovastatin

Conditions
ConditionsYield
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 1h;100%
With dmap; methanesulfonyl chloride In acetonitrile at 20℃;90%
With Burgess Reagent In benzene at 60℃; for 1.5h;61%
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 1h;460 mg
lovastatin
75330-75-5

lovastatin

N-butylamine
109-73-9

N-butylamine

N-butyl-7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutanoyl>oxy>-1(S)-naphthyl>-3(R),5(R)-dihydroxyheptanoic acid amide
134970-29-9

N-butyl-7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutanoyl>oxy>-1(S)-naphthyl>-3(R),5(R)-dihydroxyheptanoic acid amide

Conditions
ConditionsYield
at 80℃; for 1h;100%
Heating / reflux;
Reflux;
at 70℃; for 3h; Inert atmosphere;
lovastatin
75330-75-5

lovastatin

Cyclopropylamine
765-30-0

Cyclopropylamine

N-cyclopropyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(s),6(R)-dimethyl-8(s)-[[2(S)-methylbutanoyl]oxy]-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid amide

N-cyclopropyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(s),6(R)-dimethyl-8(s)-[[2(S)-methylbutanoyl]oxy]-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid amide

Conditions
ConditionsYield
at 40 - 42℃; for 8h; Inert atmosphere;100%
lovastatin
75330-75-5

lovastatin

monacolin J hydroxy acid
132748-10-8

monacolin J hydroxy acid

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; Reflux;98%
Stage #1: lovastatin; potassium hydroxide In ethanol; water at 20℃; for 12.5 - 17h; Heating / reflux;
Stage #2: With hydrogenchloride; water In diethyl ether at 5 - 10℃; for 1h; pH=5;
93%
Stage #1: lovastatin With potassium hydroxide In water; isopropyl alcohol at 80℃; for 7h;
Stage #2: With hydrogenchloride In water at 12 - 17℃; for 2h; pH=3 - 4; Cooling with ice;
90%
lovastatin
75330-75-5

lovastatin

triethylamine
121-44-8

triethylamine

(3R,5S)-7-[(1S,2S,6R,8S,8aR)-2,6-Dimethyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-3,5-dihydroxy-heptanoic acid; compound with triethyl-amine

(3R,5S)-7-[(1S,2S,6R,8S,8aR)-2,6-Dimethyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-3,5-dihydroxy-heptanoic acid; compound with triethyl-amine

Conditions
ConditionsYield
Stage #1: lovastatin With sodium hydroxide In methanol; water at 20℃; for 2h;
Stage #2: triethylamine In ethyl acetate at 20℃; for 4h;
98%
lovastatin
75330-75-5

lovastatin

(1S,3R,7S,8S,8aR)-8-((3R,5R)-3,5-dihydroxy-7-(hydroxyamino)-7-oxoheptyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (S)-2-methylbutanoate

(1S,3R,7S,8S,8aR)-8-((3R,5R)-3,5-dihydroxy-7-(hydroxyamino)-7-oxoheptyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (S)-2-methylbutanoate

Conditions
ConditionsYield
With hydroxylamine In tetrahydrofuran; water for 72h;98%
With hydroxylamine In tetrahydrofuran; water at 20℃; for 1h;92%
lovastatin
75330-75-5

lovastatin

7-[1',2',6',7',8',8a'(R)-hexahydro-2'(S),6'(R)-dimethyl-8'(S)-hydroxy-1'(S)-naphthyl]-3(R),5 (R)-dihydroxy heptanoic acid

7-[1',2',6',7',8',8a'(R)-hexahydro-2'(S),6'(R)-dimethyl-8'(S)-hydroxy-1'(S)-naphthyl]-3(R),5 (R)-dihydroxy heptanoic acid

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran; water at -30 - 20℃; for 5h;94%
pivaloyl chloride
3282-30-2

pivaloyl chloride

lovastatin
75330-75-5

lovastatin

(2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl 2,2-dimethylpropanoate
479482-41-2

(2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl 2,2-dimethylpropanoate

Conditions
ConditionsYield
With pyridine In toluene at 20℃;92%
With pyridine In toluene at 20℃; for 24h; Inert atmosphere;77%
benzoyl chloride
98-88-4

benzoyl chloride

lovastatin
75330-75-5

lovastatin

(2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl benzoate
81189-93-7

(2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl benzoate

Conditions
ConditionsYield
With pyridine In toluene at 20℃; for 18h;91%
With pyridine In toluene at 20℃; for 24h; Inert atmosphere;85%
lovastatin
75330-75-5

lovastatin

6(R)-<2-<1,2,3,5,6,7,8,8a(R)-Octahydro-2(S),6(R)-dimethyl-8(R)-<<2(S)-methylbutyryl>oxy>-1(S)-naphthyl>ethyl>-3,4,5,6-tetrahydro-4(R)-hydroxy-2H-pyran-2-one
79691-09-1

6(R)-<2-<1,2,3,5,6,7,8,8a(R)-Octahydro-2(S),6(R)-dimethyl-8(R)-<<2(S)-methylbutyryl>oxy>-1(S)-naphthyl>ethyl>-3,4,5,6-tetrahydro-4(R)-hydroxy-2H-pyran-2-one

Conditions
ConditionsYield
With (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; hydrogen In dichloromethane at 20℃; under 760 Torr; for 1.5h;90%
Multi-step reaction with 2 steps
1: 1.48 g / imidazole / dimethylformamide / 5 h / 35 °C
2: 50 mg / triethylsilane, trifluoroacetic acid / CH2Cl2 / 24 h / Ambient temperature
View Scheme
lovastatin
75330-75-5

lovastatin

7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-hydroxy-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid
761354-04-5

7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-hydroxy-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid

Conditions
ConditionsYield
Stage #1: lovastatin With potassium hydroxide; ethanol; water In isopropyl alcohol at 20℃; for 6.5h; Heating / reflux;
Stage #2: With hydrogenchloride In water; isopropyl alcohol for 1h; pH=<= 3;
90%
lovastatin
75330-75-5

lovastatin

A

(4R,6R)-4-hydroxy-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one
151006-15-4, 79952-42-4

(4R,6R)-4-hydroxy-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one

B

monacolin J hydroxy acid
132748-10-8

monacolin J hydroxy acid

Conditions
ConditionsYield
Stage #1: lovastatin With ammonia; water; enzyme SEQ ID NO:4 (encoded by SEQ ID NO:3) at 40℃; for 18.75 - 27h; pH=9.5; Enzymatic reaction;
Stage #2: In water pH=2.5; Product distribution / selectivity; Acidic aqueous solution;
A n/a
B 89.4%
Stage #1: lovastatin With methanol; sodium hydroxide; water at 20℃;
Stage #2: With hydrogenchloride In methanol; water pH=7 - 8;
Stage #3: With hydrogenchloride; methanol; methanesulfonic acid; ammonia; water; lovastatin esterase SEQ ID NO:4 (encoded by SEQ ID NO:3) Product distribution / selectivity; more than 3 stages;
With water; potassium hydroxide In methanol for 21h; Reflux;
lovastatin
75330-75-5

lovastatin

(4R,6R)-4-hydroxy-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one
151006-15-4, 79952-42-4

(4R,6R)-4-hydroxy-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
Stage #1: lovastatin With water; lithium hydroxide at 100℃;
Stage #2: With hydrogenchloride In water pH=< 2;
Stage #3: With calcium hydride In toluene at 110℃; for 1h;
89%
With lithium hydroxide In tetrahydrofuran; methanol at 66℃; for 2h; Inert atmosphere;73%
With lithium hydroxide for 24h; Heating;
lovastatin
75330-75-5

lovastatin

tert-butylamine
75-64-9

tert-butylamine

lovastatin tert-butylamine salt

lovastatin tert-butylamine salt

Conditions
ConditionsYield
With water at 50 - 55℃; for 3.5h;88%
lovastatin
75330-75-5

lovastatin

(1S,3R,7S,8S,8aR)-3,7-dimethyl-8-((3R,5S)-3,5,7-trihydroxyheptyl)-1,2,3,7,8,8ahexahydronaphthalen-1-yl 2-methylbutanoate
221192-13-8

(1S,3R,7S,8S,8aR)-3,7-dimethyl-8-((3R,5S)-3,5,7-trihydroxyheptyl)-1,2,3,7,8,8ahexahydronaphthalen-1-yl 2-methylbutanoate

Conditions
ConditionsYield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;87%
lovastatin
75330-75-5

lovastatin

2-naphthaloyl chloride
2243-83-6

2-naphthaloyl chloride

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

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

Conditions
ConditionsYield
With pyridine In toluene at 20℃; for 24h; Inert atmosphere;86%
lovastatin
75330-75-5

lovastatin

<1S-<1α(3R*,5S*),2α,6β,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl)-1,3,5-heptanetriol
148969-22-6

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

Conditions
ConditionsYield
With lithium aluminium tetrahydride84%
With lithium aluminium tetrahydride In tetrahydrofuran for 5h;84%
With lithium aluminium tetrahydride In diethyl ether for 3h;80%
acetic anhydride
108-24-7

acetic anhydride

lovastatin
75330-75-5

lovastatin

(S)-2-methyl-butyric acid (3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-acetoxy-6-oxo-tetrahydro-pyran-2yl]-ethyl}-3,7-dimetyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
81189-92-6

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

Conditions
ConditionsYield
With pyridine at 20℃; for 2.5h; Inert atmosphere;84%
lovastatin
75330-75-5

lovastatin

(1S,3R,7S,8S,8aR)-8-((3R,5R)-7-amino-3,5-dihydroxy-7-oxoheptyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (S)-2-methylbutanoate
118159-61-8

(1S,3R,7S,8S,8aR)-8-((3R,5R)-7-amino-3,5-dihydroxy-7-oxoheptyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (S)-2-methylbutanoate

Conditions
ConditionsYield
With ammonia In methanol at 20℃; for 24h;79%
lovastatin
75330-75-5

lovastatin

(1S,3R,7S,8S,8aR)-7,7-dideuterio-3,7-dimethyl-8-((3R,5S)-3,5,7-trihydroxyheptyl)-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2-methylbutanoate

(1S,3R,7S,8S,8aR)-7,7-dideuterio-3,7-dimethyl-8-((3R,5S)-3,5,7-trihydroxyheptyl)-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2-methylbutanoate

Conditions
ConditionsYield
With samarium diiodide; water-d2 In tetrahydrofuran at 23℃; for 2h; Inert atmosphere; chemoselective reaction;74%
succinic acid anhydride
108-30-5

succinic acid anhydride

lovastatin
75330-75-5

lovastatin

lovastatin succinate monoester

lovastatin succinate monoester

Conditions
ConditionsYield
With pyridine at 50℃; for 48h;72%
lovastatin
75330-75-5

lovastatin

chloroacetyl chloride
79-04-9

chloroacetyl chloride

C26H37ClO6

C26H37ClO6

Conditions
ConditionsYield
With pyridine In toluene at 0 - 20℃; for 18h;70%
4-(trifluoromethoxy)benzoyl chloride
36823-88-8

4-(trifluoromethoxy)benzoyl chloride

lovastatin
75330-75-5

lovastatin

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

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

Conditions
ConditionsYield
With pyridine In toluene at 20℃; for 24h; Inert atmosphere;64%
4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

lovastatin
75330-75-5

lovastatin

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

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

Conditions
ConditionsYield
With pyridine In toluene at 20℃; for 24h; Inert atmosphere;64%
4-(methylsulfinyl)benzoic acid
33963-58-5

4-(methylsulfinyl)benzoic acid

lovastatin
75330-75-5

lovastatin

(2R,4R)-2-(2-((1S,2S,6R,8S,8aR)-2,6-dimethyl-8-(((S)-2-methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)-6-oxotetrahydro-2H-pyran-4-yl 4-(methylsulfinyl)benzoate

(2R,4R)-2-(2-((1S,2S,6R,8S,8aR)-2,6-dimethyl-8-(((S)-2-methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)-6-oxotetrahydro-2H-pyran-4-yl 4-(methylsulfinyl)benzoate

Conditions
ConditionsYield
Stage #1: 4-(methylsulfinyl)benzoic acid; lovastatin With dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Inert atmosphere; Cooling with ice;
Stage #2: With dmap In dichloromethane at 20℃; for 16h; Inert atmosphere; Cooling with ice;
63%
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