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Dayang Chem (Hangzhou) Co.,Ltd.

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

Hangzhou Think Chemical Co. Ltd

(+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one CAS No.:41639-74-1 Name: (+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]f

Henan Tianfu Chemical Co., Ltd.

Product Name: HYDRIDE-L Synonyms: HYDRIDE-L;(+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one;BP-2 (LT-EDI);BP-2 (LT-EDI)(Bimaprost、Latanprost);(3aR,4R,5R,6aS)-5-Hydroxy-4-((S

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

Pharmaceutical Grade CAS 41639-74-1 with competitive price

Cas:41639-74-1

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

HYDRIDE-L

Cas:41639-74-1

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

inquiry

Qingdao Beluga Import and Export Co., LTD

HYDRIDE-L CAS:41639-74-1 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,

HYDRIDE-L CAS:41639-74-1

Cas:41639-74-1

Min.Order:1 Gram

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

Sinoway Industrial Co., Ltd.

Why is SINOWAY: 1) Specialized in pharmaceutical and healthcare industrial for 34 years. 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 c

Taizhou Crene Biotechnology co.ltd

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

HYDRIDE-L 41639-74-1

Cas:41639-74-1

Min.Order:0 Metric Ton

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

HYDRIDE-L

Cas:41639-74-1

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Afine Chemicals Limited

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

BP-2 (LT-EDI)

Cas:41639-74-1

Min.Order:1 Gram

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

cas:41639-74-1

Cas:41639-74-1

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

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

HYDRIDE-L

Cas:41639-74-1

Min.Order:100 Gram

FOB Price: $100.0 / 2000.0

Type:Lab/Research institutions

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 providing h

Factory Supply BP-2 (LT-EDI)

Cas:41639-74-1

Min.Order:0

Negotiable

Type:Other

inquiry

Siwei Development Group Ltd.

Product name: 2H-Cyclopenta[b]furan-2-One, Hexahydro-5-Hydroxy-4-[(1E,3S)-3-Hydroxy-5-Phenyl-1-Penten-1-yl]-,(3aR,4R,5R,6aS)- CAS No.:41639-74-1 Molecule Formula:C18H22O4 Molecule Weight:302.36 Purity: 98.0% Package: 25kg/drum Description:White

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,

HYDRIDE-L

Cas:41639-74-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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

HYDRIDE-L

Cas:41639-74-1

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

inquiry

Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

Product name: BP-2;(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one CAS No.: 41639-74-1 Chemical name: HYDRIDE-L;(+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl

Shandong Mopai Biotechnology Co., LTD

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

HYDRIDE-L

Cas:41639-74-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

KAISA GROUP INC

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

HYDRIDE-L

Cas:41639-74-1

Min.Order:1 Metric Ton

FOB Price: $1.5

Type:Trading Company

inquiry

Senova Technology Company Limited

1.High quality 2.High purity 3.Best price 4.Best service 5.Professional manufacturer 6.Loyal and honest supplier 7.Fast response to customer within 6 hours Application:Pharmaceutical Intermediate

SAGECHEM LIMITED

SAGECHEM is a chemical R&D, manufacturing and distribution company in China since 2009, including pharmaceutical intermediates, agrochemical, dyestuff intermediates, organosilicone, API and etc. We also offer a full range of services in custom synthe

Suzhou Health Chemicals Co., Ltd.

High quality,stable supply chain.Appearance:white/off-white or light yellow Storage:Store in cool and dry place, keep away from strong light and heat. Package:aluminum bottle,glass bottle,PTFE bottle,cardboard drum Application:This product can be use

CHANGZHOU HANGYU PHARMACEUTICAL TECHNOLOGY CO., LTD

CHANGZHOU HANGYU PHARMACEUTICAL TECHNOLOGY CO., LTD. founded in 1984, engages in pharmaceutical research, development, production, process design and technical consultation of synthetic and fermentation pharmaceutical products. The organizational s

41639-74-1manufacturer/high quality/in stock

Cas:41639-74-1

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Bluecrystal chem-union

We are a Union of chemistry in China, consists of chemists,engineers, laboratories,factories in China. We organize surplus capacity of R&D and production as well as custom synthesis for chemical products and chemical business project. We are supp

HYDRIDE-L

Cas:41639-74-1

Min.Order:1 Metric Ton

FOB Price: $1.0

Type:Trading Company

inquiry

GIHI CHEMICALS CO.,LIMITED

Lower price, sample is available,SDS test documents are available,large stock in warehouseAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:Fine chemical intermediates, used as the main raw material for the synthe

Hangzhou J&H Chemical Co., Ltd.

J&H CHEM is one of China's leading providers of integrated fine chemical services including offering, research and development, Custom manufacturing business, as well as other Value-added customer services, for diversified range products of chemicals

HYDRIDE-L

Cas:41639-74-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Antimex Chemical Limied

hight degree of purity Application:Fine chemical intermediates, used as the main raw material for he synthesis of various pesticides, medicines, surfactants, polymer monomers, Ond Ontifungal agents

Wuhan Circle Star Chem-medical Technology co.,Ltd.

good quality, competitive price, thoughtful after sale serviceAppearance:White to Off-White Solid Storage:Keep it in dry,shady and cool place Package:as your requirement Application:Pharma;Industry;Agricultural;chemical reaserch Transportation:by Sea

HYDRIDE-L

Cas:41639-74-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

(3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Stage #1: (3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one With chlorobis(2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane In tetrahydrofuran at -40℃; for 12h;
Stage #2: With hydrogenchloride In water at 20℃; for 0.5h; Reagent/catalyst; Temperature;
88%
With C20H35B In tetrahydrofuran; hexane at -40℃; for 12h;76%
(3aR,4R,5R,6aS)-4-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-2-oxo-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate
55444-68-3

(3aR,4R,5R,6aS)-4-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-2-oxo-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With potassium carbonate In methanol at 25℃; for 2h;83%
With methanol; potassium carbonate deprotection;
(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one
41639-73-0

(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With methanol; potassium carbonate80%
With potassium carbonate In tetrahydrofuran; methanol for 2.5h;
Stage #1: (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one With methanol; potassium carbonate at 20 - 30℃;
Stage #2: With hydrogenchloride In water; ethyl acetate at 20 - 30℃; for 0.5h;
benzyl(1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-hydroxy-(1E)-pentenyl]-5-oxo-cyclopentane-acetate
944269-28-7

benzyl(1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-hydroxy-(1E)-pentenyl]-5-oxo-cyclopentane-acetate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at -70℃; for 2h; Product distribution / selectivity;78%
benzyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate

benzyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Stage #1: benzyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate With L-Selectride In tetrahydrofuran at -70℃; for 2h; Cooling with methanol-dry ice;
Stage #2: With water; ammonium chloride In tetrahydrofuran Product distribution / selectivity;
78%
(1R,2'S,5'R)-methyl(1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-hydroxy-(1E)-pentenyl]-5-oxo-acetate

(1R,2'S,5'R)-methyl(1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-hydroxy-(1E)-pentenyl]-5-oxo-acetate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at -70℃; for 2h; Product distribution / selectivity;77%
(1'R,2'S,5'R)-menthyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate

(1'R,2'S,5'R)-menthyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Stage #1: (1'R,2'S,5'R)-menthyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate With L-Selectride In tetrahydrofuran at -70℃; for 2h; Cooling with methanol-dry ice;
Stage #2: With water; ammonium chloride In tetrahydrofuran Product distribution / selectivity;
77%
C38H33NO8

C38H33NO8

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With potassium carbonate In methanol; dichloromethane at 25 - 30℃; Inert atmosphere;77%
ethyl (1R,2R,3R) 3-hydroxy-2-[5-phenyl-(3S)-hydroxy-(1E)-pentenyl]-5-oxo-cyclopentane acetate

ethyl (1R,2R,3R) 3-hydroxy-2-[5-phenyl-(3S)-hydroxy-(1E)-pentenyl]-5-oxo-cyclopentane acetate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at -70℃; for 2h; Product distribution / selectivity;75%
ethyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate

ethyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Stage #1: ethyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate With L-Selectride In tetrahydrofuran at -70℃; for 2h; Cooling with methanol-dry ice;
Stage #2: With water; ammonium chloride In tetrahydrofuran Product distribution / selectivity;
75%
2-naphthyl (1R,2R,3R)-3-hydroxy-2-[(E)-5-phenyl-(3S)-hydroxy-1-pentenyl]-5-oxo-cyclopentane acetate

2-naphthyl (1R,2R,3R)-3-hydroxy-2-[(E)-5-phenyl-(3S)-hydroxy-1-pentenyl]-5-oxo-cyclopentane acetate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at -70℃; for 2h; Product distribution / selectivity;68%
2-naphthyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate

2-naphthyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Stage #1: 2-naphthyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate With L-Selectride In tetrahydrofuran at -70℃; for 2h; Cooling with methanol-dry ice;
Stage #2: With water; ammonium chloride In tetrahydrofuran Product distribution / selectivity;
68%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: H2 / 5 percent Pd/C / ethyl acetate
2.1: MeOH
3.1: N-BuLi / tetrahydrofuran / 0 °C
3.2: tetrahydrofuran
4.1: NaHMDS / 1,2-dimethoxy-ethane
4.2: 1,2-dimethoxy-ethane
5.1: (S)-BINAL-H; LiAlH4 / tetrahydrofuran
6.1: K2CO3; MeOH
View Scheme
3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-BuLi / tetrahydrofuran / 0 °C
1.2: tetrahydrofuran
2.1: NaHMDS / 1,2-dimethoxy-ethane
2.2: 1,2-dimethoxy-ethane
3.1: (S)-BINAL-H; LiAlH4 / tetrahydrofuran
4.1: K2CO3; MeOH
View Scheme
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NaHMDS / 1,2-dimethoxy-ethane
1.2: 1,2-dimethoxy-ethane
2.1: (S)-BINAL-H; LiAlH4 / tetrahydrofuran
3.1: K2CO3; MeOH
View Scheme
Multi-step reaction with 3 steps
1: 1.) NaH / 1.) THF, 90 min, 2.) THF, 30 min
2: lithium triethylborohydride / tetrahydrofuran / 0.5 h
3: potassium carbonate / methanol; tetrahydrofuran / 2.5 h
View Scheme
(3aR,4R,5R,6aS)-2-oxo-4-((1E)-3-oxo-5-phenylpent-1-en-1-yl)-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate
55076-60-3

(3aR,4R,5R,6aS)-2-oxo-4-((1E)-3-oxo-5-phenylpent-1-en-1-yl)-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (S)-BINAL-H; LiAlH4 / tetrahydrofuran
2: K2CO3; MeOH
View Scheme
Multi-step reaction with 2 steps
1: (-)-diisopinocamphenylborane chloride / dichloromethane / 26 h / -25 - 30 °C
2: potassium carbonate / methanol / 2 h / 25 °C
View Scheme
3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: MeOH
2.1: N-BuLi / tetrahydrofuran / 0 °C
2.2: tetrahydrofuran
3.1: NaHMDS / 1,2-dimethoxy-ethane
3.2: 1,2-dimethoxy-ethane
4.1: (S)-BINAL-H; LiAlH4 / tetrahydrofuran
5.1: K2CO3; MeOH
View Scheme
(1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one
41639-72-9

(1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium triethylborohydride / tetrahydrofuran / 0.5 h
2: potassium carbonate / methanol; tetrahydrofuran / 2.5 h
View Scheme
(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate
38754-71-1

(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) NaH / 1.) THF, 90 min, 2.) THF, 30 min
2: lithium triethylborohydride / tetrahydrofuran / 0.5 h
3: potassium carbonate / methanol; tetrahydrofuran / 2.5 h
View Scheme
benzoic acid (3aR,4R,5R,6aS)-4-((E)-3-hydroxy-5-phenyl-pent-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

benzoic acid (3aR,4R,5R,6aS)-4-((E)-3-hydroxy-5-phenyl-pent-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Stage #1: benzoic acid (3aR,4R,5R,6aS)-4-((E)-3-hydroxy-5-phenyl-pent-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester With methanol; sodium methylate for 2h;
Stage #2: With hydrogenchloride In methanol; water at 0 - 5℃; pH=6.5; Product distribution / selectivity;
(3aR,4R,6aS)-2-oxo-4-((E)-3-oxo-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

(3aR,4R,6aS)-2-oxo-4-((E)-3-oxo-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene; tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere
1.2: -20 - 0 °C / Inert atmosphere
1.3: pH 3
2.1: potassium carbonate; methanol / 2 h / 25 °C
View Scheme
(3aR,4R,6aS)-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

(3aR,4R,6aS)-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With methanol; potassium carbonate at 25℃; for 2h;
(3aR,4R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

(3aR,4R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydride / dichloromethane / 1 h / 0 °C
1.2: 0 - 5 °C
2.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene; tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere
2.2: -20 - 0 °C / Inert atmosphere
2.3: pH 3
3.1: potassium carbonate; methanol / 2 h / 25 °C
View Scheme
C21H20O5

C21H20O5

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -70 °C / Inert atmosphere
1.2: 1 h / Inert atmosphere
2.1: sodium hydride / dichloromethane / 1 h / 0 °C
2.2: 0 - 5 °C
3.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene; tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere
3.2: -20 - 0 °C / Inert atmosphere
3.3: pH 3
4.1: potassium carbonate; methanol / 2 h / 25 °C
View Scheme
4-Phenyl-2-butanone
2550-26-7

4-Phenyl-2-butanone

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: acetic acid; bromine / methanol / 2 h / -5 - 20 °C
2: acetonitrile / 1 h / 80 °C
3: lithium chloride; triethylamine / tetrahydrofuran / 2 h / -4 - 20 °C
4: (-)-diisopinocamphenylborane chloride / dichloromethane / 26 h / -25 - 30 °C
5: potassium carbonate / methanol / 2 h / 25 °C
View Scheme
diethyl (2-oxo-4-phenylbutyl)phosphonate
40601-45-4

diethyl (2-oxo-4-phenylbutyl)phosphonate

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium chloride; triethylamine / tetrahydrofuran / 2 h / -4 - 20 °C
2: (-)-diisopinocamphenylborane chloride / dichloromethane / 26 h / -25 - 30 °C
3: potassium carbonate / methanol / 2 h / 25 °C
View Scheme
1-bromo-4-phenylbutan-2-one
31984-10-8

1-bromo-4-phenylbutan-2-one

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetonitrile / 1 h / 80 °C
2: lithium chloride; triethylamine / tetrahydrofuran / 2 h / -4 - 20 °C
3: (-)-diisopinocamphenylborane chloride / dichloromethane / 26 h / -25 - 30 °C
4: potassium carbonate / methanol / 2 h / 25 °C
View Scheme
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
5307-99-3

(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: (S)-6,6'-bis(2,4,6-triisopropylphenyl)-1,1'-spirobiindane-7,7'-diyl hydrogenphosphate; dihydrogen peroxide / chloroform; water / -15 °C / Schlenk technique
2.1: ammonium chloride; zinc / methanol / 3 h / 70 °C
3.1: formic acid; sulfuric acid / 24 h / 80 °C
3.2: 2 h / 0 - 20 °C
4.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; N,N-dimethyl acetamide / 6 h / 20 °C
5.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
5.2: 6 h / 0 - 20 °C / Inert atmosphere
6.1: C20H35B / tetrahydrofuran; hexane / 12 h / -40 °C
View Scheme
Multi-step reaction with 6 steps
1.1: (S)-6,6'-bis(2,4,6-triisopropylphenyl)-1,1'-spirobiindane-7,7'-diyl hydrogenphosphate; dihydrogen peroxide / chloroform; water / 48 h / 0 °C / Schlenk technique
2.1: ammonium chloride; zinc / methanol / 3 h / 70 °C
3.1: formic acid; sulfuric acid / 24 h / 80 °C
3.2: 2 h / 0 - 20 °C
4.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; N,N-dimethyl acetamide / 6 h / 20 °C
5.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
5.2: 6 h / 0 - 20 °C / Inert atmosphere
6.1: C20H35B / tetrahydrofuran; hexane / 12 h / -40 °C
View Scheme
(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one
26054-46-6

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: formic acid; sulfuric acid / 24 h / 80 °C
1.2: 2 h / 0 - 20 °C
2.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; N,N-dimethyl acetamide / 6 h / 20 °C
3.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
3.2: 6 h / 0 - 20 °C / Inert atmosphere
4.1: C20H35B / tetrahydrofuran; hexane / 12 h / -40 °C
View Scheme
(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

(1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one
145667-75-0

(1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; sodium hydroxide In ethanol at 20℃; under 760.051 Torr; for 5h;100%
With palladium 10% on activated carbon; hydrogen; sodium hydroxide In ethanol at 20℃; under 3000.3 Torr;85%
With sodium hydroxide; hydrogen; 5%-palladium/activated carbon In ethyl acetate Product distribution / selectivity;78%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

(3aR,4R,5R,6aS)-hexahydro-4-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)cyclopenta[b]furan-2-one
69610-63-5

(3aR,4R,5R,6aS)-hexahydro-4-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)cyclopenta[b]furan-2-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 2.5h;89.9%
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 2.5h;89.9%
With toluene-4-sulfonic acid In dichloromethane for 0.5h;
With toluene-4-sulfonic acid In dichloromethane Etherification;
(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

(3aR,4R,5R,6aS)-4-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2,5-diol
856240-62-5

(3aR,4R,5R,6aS)-4-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2,5-diol

Conditions
ConditionsYield
With diisobutylaluminium hydride In tetrahydrofuran at -70℃; for 2h;81%
With diisobutylaluminium hydride
With diisobutylaluminium hydride In dichloromethane at -78℃; for 2h;
Stage #1: (3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one With diisobutylaluminium hydride In dichloromethane at -78℃; for 2h;
Stage #2: With ammonium chloride at 20℃; for 0.25h; Reagent/catalyst; Temperature;
(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-5-phenyl-pent-1-enyl)-cyclopentyl]-hept-5-enoic acid

(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-5-phenyl-pent-1-enyl)-cyclopentyl]-hept-5-enoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: p-TSA / CH2Cl2
2: DIBAL-H / -78 °C
3: NaHMDS
4: aq. AcOH / tetrahydrofuran
View Scheme
(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((R)-3-hydroxy-5-phenyl-pentyl)-cyclopentyl]-heptanoic acid

7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((R)-3-hydroxy-5-phenyl-pentyl)-cyclopentyl]-heptanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: p-TSA / CH2Cl2
2: DIBAL-H / -78 °C
3: NaHMDS
4: aq. AcOH / tetrahydrofuran
5: H2 / 5 percent Pd/C / ethyl acetate
View Scheme
(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetaldehyde

[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: p-TSA / CH2Cl2
2: DIBAL-H / -78 °C
View Scheme
(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

7-((1R,2R,3R,5S)-5-hydroxy-2-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid

7-((1R,2R,3R,5S)-5-hydroxy-2-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: p-TSA / CH2Cl2
2: DIBAL-H / -78 °C
3: NaHMDS
View Scheme
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 2.5 h / 20 °C
2.1: diisobutylaluminium hydride / toluene; hexane / -70 °C
3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / -20 °C
3.2: 16 h / -20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 2.5 h / 20 °C
2.1: diisobutylaluminium hydride / hexane; toluene / -70 °C
3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / -20 °C
3.2: 16 h / -20 °C
View Scheme
(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

N-(methanesulfonyl)-17-phenyl-ω-trinor-PGE2-carboxamide
69590-43-8

N-(methanesulfonyl)-17-phenyl-ω-trinor-PGE2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: p-toluenesulfonic acid / CH2Cl2 / 0.5 h
2: diisobutylaluminum hydride / toluene; hexane / 0.33 h
3: 1.) sodium methylsulfinylcarbanide / 1.) Me2SO, 2.) Me2SO, 2 h
4: Jones reagent / acetone / 0.08 h / -20 °C
5: 65percent aq. acetic acid / 14 h / Ambient temperature
View Scheme
(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

(3aR,4R,5R,6aS)-hexahydro-4-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)-2H-cyclopenta[b]furan-2-ol
856453-32-2

(3aR,4R,5R,6aS)-hexahydro-4-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)-2H-cyclopenta[b]furan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: p-toluenesulfonic acid / CH2Cl2 / 0.5 h
2: diisobutylaluminum hydride / toluene; hexane / 0.33 h
View Scheme
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / dichloromethane / 2.5 h / 20 °C
2: diisobutylaluminium hydride / toluene; hexane / -70 °C
View Scheme
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / dichloromethane / 2.5 h / 20 °C
2: diisobutylaluminium hydride / hexane; toluene / -70 °C
View Scheme
(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

N-{(Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoyl}-methanesulfonamide
69590-40-5

N-{(Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoyl}-methanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: p-toluenesulfonic acid / CH2Cl2 / 0.5 h
2: diisobutylaluminum hydride / toluene; hexane / 0.33 h
3: 1.) sodium methylsulfinylcarbanide / 1.) Me2SO, 2.) Me2SO, 2 h
View Scheme
(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one
41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

N-{(Z)-7-[(1R,2R,3R)-5-Oxo-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoyl}-methanesulfonamide
69590-42-7

N-{(Z)-7-[(1R,2R,3R)-5-Oxo-2-[(E)-(S)-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoyl}-methanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: p-toluenesulfonic acid / CH2Cl2 / 0.5 h
2: diisobutylaluminum hydride / toluene; hexane / 0.33 h
3: 1.) sodium methylsulfinylcarbanide / 1.) Me2SO, 2.) Me2SO, 2 h
4: Jones reagent / acetone / 0.08 h / -20 °C
View Scheme

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