209861-02-9

Basic information

• Product Name: TF-Diol
• Synonyms: TF-Diol;(3aR,4R,5R,6aS)-4-((1E)-3,3-Difluoro-4-phenoxy-1-buten-1-yl)hexahydro-2H-cyclopenta[b]furan-2,5-diol (TF-Diol);2H-Cyclopenta[b]furan-2,5-diol,4-[(1E)-3,3-difluoro-4-phenoxy-1-buten-1-yl]hexahydro-(3aR,4R,5R,6aS)-;(3aR,4R,5R,6aS)-4-[(1E)-3,3-Difluoro-4-phenoxy-1-butenyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol;TF-DI
• CAS NO: 209861-02-9
• Molecular Formula: C₁₇H₂₀F₂O₄
• Molecular Weight: 326.3351064
• Mol File: 209861-02-9.mol

Chemical Properties

• Boiling Point: 481.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.361±0.06 g/cm3(Predicted)
• PKA: 13.01±0.60(Predicted)
• CAS DataBase Reference: TF-Diol(CAS DataBase Reference)
• NIST Chemistry Reference: TF-Diol(209861-02-9)
• EPA Substance Registry System: TF-Diol(209861-02-9)

Safety Data

• Hazardous Substances Data: 209861-02-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
TF-Diol is used as a building block for the synthesis of various pharmaceuticals due to its unique properties that enhance the reactivity and selectivity of other compounds, contributing to the development of novel and effective medications.
Used in Agrochemical Industry:
In the agrochemical sector, TF-Diol is utilized as a key component in the creation of new agrochemicals, leveraging its stability and reactivity-modifying capabilities to improve the performance and safety of these products.
Used in Advanced Materials:
TF-Diol is employed as a crucial constituent in the development of advanced materials, where its high stability and ability to influence the properties of other compounds are particularly beneficial for creating materials with enhanced performance characteristics.
Used in Organic Synthesis:
TF-Diol is used as a versatile intermediate in organic synthesis, where its unique structure and properties facilitate the creation of a wide range of organic compounds for various applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, TF-Diol is applied as a valuable chemical entity for the design and synthesis of new drugs, taking advantage of its potential to modify the reactivity and selectivity of other compounds to achieve desired therapeutic effects.

Upstream product

• 163074-98-4 [(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-(phenylmethoxy)-2H-cyclopenta[b]furan-4-carboxaldehyde] 
• 81190-06-9 [(3aR,4S,5R,6aS)-hexahydro-4-(hydroxymethyl)-5-(phenylmethoxy)-2H-cyclopenta[b]furan-2-one] 
• 209861-00-7 (3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybutan-1-en-1-yl)-hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl benzoate 
• 51638-91-6 (3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate 
• 209861-01-8 (3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one 
• 29782-85-2 rac-(trans)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol 
• 1487-05-4 rac-(trans)-3,3-dimethyltetrahydro-5H-oxireno[2',3':3,4]cyclopenta[1,2-d][1,3]dioxole 
• 5623-52-9 rac-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxole 

Downstream Products

• 209860-88-8 AFP-172 
• 209860-89-9 1-(5Z)-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenylamino-1-butenyl]-dihydroxycyclopentyl}-5-ethylheptenoate 
• 209860-87-7 tafluprost 
• 1449413-13-1 C₂₂H₂₈F₂O₅*C₁₂H₂₃N 

Relevant articles and documents

Method for large-scale preparation of tafluprost

The invention discloses a method for industrially preparing tafluprost. The method comprises the following steps: taking Corey lactone as an initial raw material, oxidizing, condensing, fluorinating,deprotecting, reducing, re-condensing, esterifying and r

An Asymmetric Suzuki-Miyaura Approach to Prostaglandins: Synthesis of Tafluprost

We report the catalytic asymmetric synthesis of Tafluprost (1), a prostaglandin analogue. This synthesis demonstrates a new approach to prostaglandins involving symmetrization and desymmetrization of a racemic precursor to control the absolute and relative stereochemistry of the cyclopentyl core. Key steps include a diastereo- and enantioselective Rh-catalyzed Suzuki-Miyaura reaction of a racemic bicyclic allyl chloride and an alkenyl boronic acid and a regio- and diastereoselective Pd-catalyzed Tsuji-Trost reaction with an enolate surrogate.

METHOD OF PURIFICATION OF PROSTAGLANDINS INCLUDING FLUORINE ATOMS BY PREPARATIVE HPLC

The present invention discloses a method of purification of prostaglandins including fluorine atoms by using preparative HPLC. Tafluprost and Travoprost are prostaglandins including fluorine. The chemical structure of the impurities in crude Tafluprost an

AMINE SALTS OF PROSTAGLANDIN ANALOGS

The present application relates to amine salts of prostaglandin analogs and their uses for the preparation of substantially pure prostaglandin analogs. Specific embodiments relate to amine salts of tafluprost and their uses for the preparation of substant

Synthesis of the highly potent prostanoid FP receptor agonist, AFP-168: A novel 15-deoxy-15,15-difluoroprostaglandin F2α derivative

A novel 15-deoxy-15,15-difluoro-prostaglandin(PG)F2α derivative 6 (AFP-168) has been synthesized from the Corey aldehyde in six steps. A key aspect of this route is difluorination of an enone and a stereoselective Wittig reaction. The compound shows high affinity to the FP receptor and potent activities for an anti-glaucoma agent.

Synthesis and biological properties of novel fluoroprostaglandin derivatives: Highly selective and potent agonists for prostaglandin receptors

Synthesis of novel 7,7-difluoroprostacyclin and 15-deoxy-15,15-difluoro- PGF2α derivatives will be presented. These compounds show high affinity to prostaglandin receptors and potent biological activities.

Difluoroprostaglandin derivatives and their use

A fluorine-containing prostaglandin derivative of the formula (1) (or a salt thereof) and a medicine containing it, particularly, a preventive or therapeutic medicine for an eye disease: STR1 wherein A is a vinylene group or the like, R1 is an