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Cas Database

1000025-92-2

1000025-92-2

Identification

Synonyms:QC-6486;3,5-bis(benzyloxy)picolinonitrile;3,5-Bis-benzyloxypyridine-2-carbonitrile;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Matrix Scientific
  • Product Description:3,5-Bis(benzyloxy)picolinonitrile 95+%
  • Packaging:1g
  • Price:$ 1647
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:3,5-Bis(benzyloxy)picolinonitrile 95+%
  • Packaging:250mg
  • Price:$ 742
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  • Manufacture/Brand:Crysdot
  • Product Description:3,5-Bis(benzyloxy)picolinonitrile 95+%
  • Packaging:1g
  • Price:$ 972
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  • Manufacture/Brand:Chemenu
  • Product Description:3,5-Bis(benzyloxy)picolinonitrile 95%
  • Packaging:1g
  • Price:$ 916
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:3,5-BIS(BENZYLOXY)PICOLINONITRILE 95.00%
  • Packaging:5MG
  • Price:$ 501.53
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  • Manufacture/Brand:AK Scientific
  • Product Description:3,5-Bis(benzyloxy)picolinonitrile
  • Packaging:1g
  • Price:$ 2273
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  • Manufacture/Brand:AK Scientific
  • Product Description:3,5-Bis(benzyloxy)picolinonitrile
  • Packaging:250mg
  • Price:$ 1051
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Relevant articles and documentsAll total 4 Articles be found

COMPOUNDS HAVING HEPATIAL DISEASE EFFECTIVE

-

Paragraph 0140-0141; 0147, (2021/01/29)

The invention discloses a compound with a hepatopathy curative effect, and the compound is a compound shown as a general formula (I), an optical isomer or pharmaceutically acceptable salt thereof, canbe applied to treatment or prevention of hepatopathy, particularly to drugs for treating or preventing fatty liver, liver fibrosis or liver cirrhosis, and has a good application prospect.

Design of Development Candidate eFT226, a First in Class Inhibitor of Eukaryotic Initiation Factor 4A RNA Helicase

Ernst, Justin T.,Thompson, Peggy A.,Nilewski, Christian,Sprengeler, Paul A.,Sperry, Samuel,Packard, Garrick,Michels, Theodore,Xiang, Alan,Tran, Chinh,Wegerski, Christopher J.,Eam, Boreth,Young, Nathan P.,Fish, Sarah,Chen, Joan,Howard, Haleigh,Staunton, Jocelyn,Molter, Jolene,Clarine, Jeff,Nevarez, Andres,Chiang, Gary G.,Appleman, Jim R.,Webster, Kevin R.,Reich, Siegfried H.

supporting information, p. 5879 - 5955 (2020/07/03)

Dysregulation of protein translation is a key driver for the pathogenesis of many cancers. Eukaryotic initiation factor 4A (eIF4A), an ATP-dependent DEAD-box RNA helicase, is a critical component of the eIF4F complex, which regulates cap-dependent protein synthesis. The flavagline class of natural products (i.e., rocaglamide A) has been shown to inhibit protein synthesis by stabilizing a translation-incompetent complex for select messenger RNAs (mRNAs) with eIF4A. Despite showing promising anticancer phenotypes, the development of flavagline derivatives as therapeutic agents has been hampered because of poor drug-like properties as well as synthetic complexity. A focused effort was undertaken utilizing a ligand-based design strategy to identify a chemotype with optimized physicochemical properties. Also, detailed mechanistic studies were undertaken to further elucidate mRNA sequence selectivity, key regulated target genes, and the associated antitumor phenotype. This work led to the design of eFT226 (Zotatifin), a compound with excellent physicochemical properties and significant antitumor activity that supports clinical development.

EIF4A-INHIBITING COMPOUNDS AND METHODS RELATED THERETO

-

Paragraph 0548; 0549, (2017/08/01)

The present invention provides synthesis, pharmaceutically acceptable formulations and uses of compounds in accordance with Formula I, or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof. For Formula I compounds X, Y, R1, R2, R3a, R3b, R4a, R4b and R5 are as defined in the specification. The inventive Formula I compounds are inhibitors of eIF4A and find utility in any number of therapeutic applications, including but not limited to treatment of inflammation and various cancers.

Prolyl hydroxylase inhibitors and methods of use

-

Page/Page column 9, (2008/06/13)

The present disclosure relates to HIF-1α prolyl hydroxylase inhibitors, compositions which comprise the HIF-1α prolyl hydroxylase inhibitors described herein and to methods for controlling, inter alia, Peripheral Vascular Disease (PVD), Coronary Artery Disease (CAD), heart failure, ischemia, and anemia.

Process route upstream and downstream products

Process route

2-Cyano-3,5-dichloropyridine
85331-33-5

2-Cyano-3,5-dichloropyridine

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

3,5-bis(benzyloxy)picolinonitrile
1000025-92-2

3,5-bis(benzyloxy)picolinonitrile

Conditions
Conditions Yield
With sodium hydride; In tetrahydrofuran; at 0 - 190 ℃; for 5h; microwave;
94%
2-Cyano-3,5-dichloropyridine; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h;
benzyl alcohol; In tetrahydrofuran; mineral oil; at 20 ℃;
76.6%
2-Cyano-3,5-dichloropyridine; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h; Inert atmosphere;
benzyl alcohol; In tetrahydrofuran; for 3h; Inert atmosphere;
2-Cyano-3,5-dichloropyridine; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h; Inert atmosphere;
benzyl alcohol; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;
3,5-bis(benzyloxy)picolinonitrile
1000025-92-2

3,5-bis(benzyloxy)picolinonitrile

methylmagnesium bromide
75-16-1

methylmagnesium bromide

1-(3,5-bis(benzyloxy)pyridin-2-yl)ethan-1-one

1-(3,5-bis(benzyloxy)pyridin-2-yl)ethan-1-one

Conditions
Conditions Yield
In tetrahydrofuran; at -30 - 20 ℃; for 2.5h;
95%
3,5-bis(benzyloxy)picolinonitrile; methylmagnesium bromide; In tetrahydrofuran; at -30 - 20 ℃; for 2.5h;
With hydrogenchloride; water; In tetrahydrofuran; for 2h;
82 g
3,5-bis(benzyloxy)picolinonitrile; methylmagnesium bromide; In tetrahydrofuran; at -30 - 20 ℃;
With hydrogenchloride; water; In tetrahydrofuran; for 2h;
3,5-bis(benzyloxy)picolinonitrile
1000025-92-2

3,5-bis(benzyloxy)picolinonitrile

3,5-bis-benzyloxy-pyridine-2-carboxylic acid hydrochloride

3,5-bis-benzyloxy-pyridine-2-carboxylic acid hydrochloride

Conditions
Conditions Yield
3,5-bis(benzyloxy)picolinonitrile; With sodium hydroxide; In methanol; water; for 16h; Heating / reflux;
With hydrogenchloride; In water; pH=1 - 2;
100%
3,5-bis(benzyloxy)picolinonitrile
1000025-92-2

3,5-bis(benzyloxy)picolinonitrile

rac-methyl (5aR,6S,7R,8aR)-3-(benzyloxy)-5a-(4-bromophenyl)-8a-hydroxy-8-oxo-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxylate

rac-methyl (5aR,6S,7R,8aR)-3-(benzyloxy)-5a-(4-bromophenyl)-8a-hydroxy-8-oxo-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 15 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
With hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; potassium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; acetone; acetonitrile;
Multi-step reaction with 7 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 24 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
With hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; potassium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; acetone; acetonitrile;
Multi-step reaction with 7 steps
1.1: tetrahydrofuran / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / Inert atmosphere
3.2: 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 2 h / 85 °C
5.1: sodium hydroxide; dihydrogen peroxide / water; ethanol; dichloromethane / 1 h / 20 °C
5.2: Cooling
6.1: methanol; dichloromethane; acetonitrile / 15 h / 20 °C / UV-irradiation
7.1: sodium methylate / methanol / 1 h / Heating
With hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; potassium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; acetonitrile; 4.1: |Aldol Condensation / 5.1: |Algar-Flynn-Olyamada Reaction;
3,5-bis(benzyloxy)picolinonitrile
1000025-92-2

3,5-bis(benzyloxy)picolinonitrile

rac-methyl (5aR,6S,7R,8R,8aS)-3-cyano-5a-(4-cyanophenyl)-8,8a-dihydroxy-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxylate

rac-methyl (5aR,6S,7R,8R,8aS)-3-cyano-5a-(4-cyanophenyl)-8,8a-dihydroxy-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 12 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 15 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
10.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
12.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
Multi-step reaction with 12 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 24 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
10.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
12.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
Multi-step reaction with 12 steps
1.1: tetrahydrofuran / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / Inert atmosphere
3.2: 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 2 h / 85 °C
5.1: sodium hydroxide; dihydrogen peroxide / water; ethanol; dichloromethane / 1 h / 20 °C
5.2: Cooling
6.1: methanol; dichloromethane; acetonitrile / 15 h / 20 °C / UV-irradiation
7.1: sodium methylate / methanol / 1 h / Heating
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Heating
10.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
12.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 3 h / Inert atmosphere; Heating
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 4.1: |Aldol Condensation / 5.1: |Algar-Flynn-Olyamada Reaction;
3,5-bis(benzyloxy)picolinonitrile
1000025-92-2

3,5-bis(benzyloxy)picolinonitrile

rac-methyl (5aR,6S,7R,8R,8aS)-3-(benzyloxy)-5a-(4-bromophenyl)-8,8a-dihydroxy-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxylate

rac-methyl (5aR,6S,7R,8R,8aS)-3-(benzyloxy)-5a-(4-bromophenyl)-8,8a-dihydroxy-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 8 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 15 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
With hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; acetone; acetonitrile;
Multi-step reaction with 8 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 24 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
With hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; acetone; acetonitrile;
Multi-step reaction with 8 steps
1.1: tetrahydrofuran / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / Inert atmosphere
3.2: 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 2 h / 85 °C
5.1: sodium hydroxide; dihydrogen peroxide / water; ethanol; dichloromethane / 1 h / 20 °C
5.2: Cooling
6.1: methanol; dichloromethane; acetonitrile / 15 h / 20 °C / UV-irradiation
7.1: sodium methylate / methanol / 1 h / Heating
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
With hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; acetonitrile; 4.1: |Aldol Condensation / 5.1: |Algar-Flynn-Olyamada Reaction;
3,5-bis(benzyloxy)picolinonitrile
1000025-92-2

3,5-bis(benzyloxy)picolinonitrile

rac-methyl (5aR,6S,7R,8R,8aS)-3-(benzyloxy)-5a-(4-cyanophenyl)-8,8a-dihydroxy-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxylate

rac-methyl (5aR,6S,7R,8R,8aS)-3-(benzyloxy)-5a-(4-cyanophenyl)-8,8a-dihydroxy-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 9 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 15 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; sodium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
Multi-step reaction with 9 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 24 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; sodium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
Multi-step reaction with 9 steps
1.1: tetrahydrofuran / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / Inert atmosphere
3.2: 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 2 h / 85 °C
5.1: sodium hydroxide; dihydrogen peroxide / water; ethanol; dichloromethane / 1 h / 20 °C
5.2: Cooling
6.1: methanol; dichloromethane; acetonitrile / 15 h / 20 °C / UV-irradiation
7.1: sodium methylate / methanol / 1 h / Heating
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Heating
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; sodium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 4.1: |Aldol Condensation / 5.1: |Algar-Flynn-Olyamada Reaction;
3,5-bis(benzyloxy)picolinonitrile
1000025-92-2

3,5-bis(benzyloxy)picolinonitrile

rac-(5aR,6S,7R,8R,8aS)-3-cyano-5a-(4-cyanophenyl)-8,8a-dihydroxy-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxylic acid

rac-(5aR,6S,7R,8R,8aS)-3-cyano-5a-(4-cyanophenyl)-8,8a-dihydroxy-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxylic acid

Conditions
Conditions Yield
Multi-step reaction with 13 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 15 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
10.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
12.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
13.1: lithium hydroxide / tetrahydrofuran; water / 6 h / 20 °C
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
Multi-step reaction with 13 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 24 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
10.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
12.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
13.1: lithium hydroxide / tetrahydrofuran; water / 6 h / 20 °C
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
Multi-step reaction with 13 steps
1.1: tetrahydrofuran / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / Inert atmosphere
3.2: 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 2 h / 85 °C
5.1: sodium hydroxide; dihydrogen peroxide / water; ethanol; dichloromethane / 1 h / 20 °C
5.2: Cooling
6.1: methanol; dichloromethane; acetonitrile / 15 h / 20 °C / UV-irradiation
7.1: sodium methylate / methanol / 1 h / Heating
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Heating
10.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
12.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 3 h / Inert atmosphere; Heating
13.1: lithium hydroxide / water / 6 h / 20 °C
13.2: 0 °C / pH Ca. 3
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 4.1: |Aldol Condensation / 5.1: |Algar-Flynn-Olyamada Reaction;
3,5-bis(benzyloxy)picolinonitrile
1000025-92-2

3,5-bis(benzyloxy)picolinonitrile

rac-methyl (5aR,6S,7R,8R,8aS)-5a-(4-cyanophenyl)-3,8,8a-trihydroxy-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxylate

rac-methyl (5aR,6S,7R,8R,8aS)-5a-(4-cyanophenyl)-3,8,8a-trihydroxy-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 10 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 15 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
10.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; sodium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
Multi-step reaction with 10 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 24 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
10.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; sodium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
Multi-step reaction with 10 steps
1.1: tetrahydrofuran / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / Inert atmosphere
3.2: 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 2 h / 85 °C
5.1: sodium hydroxide; dihydrogen peroxide / water; ethanol; dichloromethane / 1 h / 20 °C
5.2: Cooling
6.1: methanol; dichloromethane; acetonitrile / 15 h / 20 °C / UV-irradiation
7.1: sodium methylate / methanol / 1 h / Heating
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Heating
10.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; sodium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 4.1: |Aldol Condensation / 5.1: |Algar-Flynn-Olyamada Reaction;
3,5-bis(benzyloxy)picolinonitrile
1000025-92-2

3,5-bis(benzyloxy)picolinonitrile

rac-(5aR,6S,7R,8R,8aS)-3-cyano-5a-(4-cyanophenyl)-8,8a-dihydroxy-N,N-dimethyl-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxamide

rac-(5aR,6S,7R,8R,8aS)-3-cyano-5a-(4-cyanophenyl)-8,8a-dihydroxy-N,N-dimethyl-6-phenyl-5a,7,8,8a-tetrahydro-6H-cyclopenta[4,5]furo[3,2-b]pyridine-7-carboxamide

Conditions
Conditions Yield
Multi-step reaction with 14 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 15 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
10.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
12.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
13.1: lithium hydroxide / tetrahydrofuran; water / 6 h / 20 °C
14.1: triethylamine / dichloromethane / 0.08 h / 0 °C
14.2: 4 h / 0 - 20 °C
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
Multi-step reaction with 14 steps
1.1: tetrahydrofuran / 2.5 h / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 0.5 h / Reflux
5.1: sodium hydroxide; dihydrogen peroxide / dichloromethane; ethanol / 1 h / 20 °C
6.1: methanol; dichloromethane; acetonitrile / 24 h / UV-irradiation
7.1: sodium methylate / methanol / 1 h / 70 °C
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
10.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
12.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / 125 °C / Inert atmosphere
13.1: lithium hydroxide / tetrahydrofuran; water / 6 h / 20 °C
14.1: triethylamine / dichloromethane / 0.08 h / 0 °C
14.2: 4 h / 0 - 20 °C
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
Multi-step reaction with 14 steps
1.1: tetrahydrofuran / -30 - 20 °C
1.2: 2 h
2.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
3.1: potassium carbonate / acetone / Inert atmosphere
3.2: 3 h / Inert atmosphere
4.1: sodium hydroxide / methanol / 2 h / 85 °C
5.1: sodium hydroxide; dihydrogen peroxide / water; ethanol; dichloromethane / 1 h / 20 °C
5.2: Cooling
6.1: methanol; dichloromethane; acetonitrile / 15 h / 20 °C / UV-irradiation
7.1: sodium methylate / methanol / 1 h / Heating
8.1: acetic acid; sodium tris(acetoxy)borohydride / acetonitrile / 4 h / 20 °C
9.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Heating
10.1: palladium(II) hydroxide; hydrogen / ethyl acetate / 16 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
12.1: zinc; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 3 h / Inert atmosphere; Heating
13.1: lithium hydroxide / water / 6 h / 20 °C
13.2: 0 °C / pH Ca. 3
14.1: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane; ethyl acetate / 4 h / 0 - 20 °C
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); hydrogen; dihydrogen peroxide; sodium methylate; palladium(II) hydroxide; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hydroxide; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 4.1: |Aldol Condensation / 5.1: |Algar-Flynn-Olyamada Reaction;

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