913258-22-7

Upstream product

• 768-56-9 4-Phenylbut-1-ene 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 1126-76-7 1,2-Epoxy-4-phenylbutane 
• 20296-07-5 1-hydroxy-4-phenyl-2-butanone 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 1589-82-8 phenylmagnesium bromide 
• 157732-87-1 (4S)-2,2-dimethyl-4-(2-phenylethyl)-1,3-dioxolane 
• 152203-65-1 (4S)-2,2-dimethyl-4-styryl-1,3-dioxolane 
• 118629-73-5 (S)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate 
• 124988-64-3 (S)-4-phenyl-1,2-butanediol 
• 913258-19-2 (S)-4-phenyl-1-(p-tolylsulfonyloxy)-2-(triethylsiloxy)butane 
• 913258-20-5 (S)-4-phenyl-1-iodo-2-(triethylsiloxy)butane 
• 913258-23-8 (S)-2-hydroxy-1-iodo-4-phenylbutane 

Downstream Products

• 60340-28-5 (S)-1-phenyl-5-hexen-3-ol 
• 160805-51-6 5-phenyl-3<(tert-butyldimethylsilyl)oxy>-pentene 
• 474944-31-5 (3S)-3-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-5-phenylpentan-1-ol 
• 876953-73-0 tert-butyl[(1S)-3-iodo-1-phenethylpropyl]oxydimethylsilane 
• 37904-38-4 (3S)-5-phenyl-1-penten-3-ol 
• 130209-82-4 latanoprost 
• 352276-28-9 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-ol 
• 41639-83-2 latanoprost acid 
• 60340-28-5 (R)-1-phenyl-hex-5-en-3-ol 
• 105836-17-7 (R)-1-phenyl-3-pentanol 
• 512844-86-9 (S)-1-phenyl-5-hexyn-3-ol 
• 915105-95-2 C₁₄H₁₅⁽²⁾HO₂ 

Relevant academic research and scientific papers

Concise, scalable and enantioselective total synthesis of prostaglandins

Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. [Figure not available: see fulltext.]

Stereospecific Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Tosylate and Allyl Alcohol Electrophiles

The stereospecific cross-coupling of easily accessed electrophiles holds significant promise in the construction of C-C bonds. Herein, we report a nickel-catalyzed reductive coupling of allyl alcohols with chiral, nonracemic alkyl tosylates. This cross-coupling delivers valuable allylation products with high levels of stereospecificity across a range of substrates. The catalytic system consists of a simple nickel salt in conjunction with a commercially available reductant and importantly represents a rare example of a cross-coupling involving the C-O bonds of two electrophiles.

A new monooxygenase from: Herbaspirillum huttiense catalyzed highly enantioselective epoxidation of allylbenzenes and allylic alcohols

Asymmetric epoxidation is a green route to enantiopure epoxides, but often suffers from low enantioselectivity toward unconjugated terminal alkenes. Mining of the NCBI non-redundant protein sequences with a reconstructed ancestral sequence based on six st

Enantioselective Resolution Copolymerization of Racemic Epoxides and Anhydrides: Efficient Approach for Stereoregular Polyesters and Chiral Epoxides

Herein we report an efficient strategy for preparing isotactic polyesters and chiral epoxides via enantioselective resolution copolymerization of racemic terminal epoxides with anhydrides, mediated by enantiopure bimetallic complexes in conjunction with a nucleophilic cocatalyst. The chirality of both the axial linker and the diamine backbones of the ligand are responsible for the chiral induction of this kinetic resolution copolymerization process. The catalyst systems exhibit exceptional levels of enantioselectivity with a kinetic resolution coefficient exceeding 300 for various racemic epoxides, affording highly isotactic copolymers (selectivity factors of more than 300) with a completely alternating structure and low polydispersity index. Most of the produced isotactic polyesters are typical semicrystalline materials with melting temperatures in the range from 77 to 160 °C.

Compound And Method

A compound of formula (I): (I) wherein Y is, Z is OR10, NR11R11 SR11, S(0)R11 S02R11, R10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO—R11, or a protecting group, and R11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I). wherein Y is

COMPOUND AND METHOD

A compound of formula (I): (I) wherein Y is, Z is OR10, NR11R11 SR11, S(0)R11 S02R11, R10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO-R11, or a protecting group, and R11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I).

Enantio- and diastereocontrolled total synthesis of (+)-strictifolione

A concise and practical enantioselective synthesis of (+)-strictifolione has been achieved in high diastereomeric excess using Jacobsen's hydrolytic kinetic resolution, proline-catalyzed sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination o

PROCESS FOR PRODUCING OPTICALLY ACTIVE CIS-SILYL OLEFIN OXIDE COMPOUND

The present invention provides an efficient production method of an optically active cis-silylolefin oxide compound useful as an intermediate for various compounds. A production method of an optically active cis-silylolefin oxide compound by subjecting an

A new synthetic approach to high-purity (15R)-latanoprost

This paper describes a new synthesis of latanoprost (1) that afforded high purity latanoprost in 16.9 % overall yield in eight synthetic steps from sulfone 4. The "a chain" in a derivative of the (-)-"Corey lactone" was elongated first, followed by the attachment of a novel, enantiomerically pure "ω chain" synthon. This ensured the absence of the undesired (15S)-1 diastereomer in the synthesized prostaglandin. The crystalline nature of the novel sulfone 4 facilitated its purification. A variation of the new synthesis of latanoprost is described, where the laboratory-scale synthesis was further adapted to a hundred-gram scale. In the course of the present synthesis, a new prostaglandin sulfone intermediate, 21, which may find application in the synthesis of diverse prostaglandin analogs, was introduced. A practical synthesis of novel, enantiomerically pure "ω chain" synthons 15, 16, and 17 has also been carried out, employing diol 12, which was obtained from derivatives of the D-mannitol chiral pool. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

PROCESS FOR PREPARATION OF 13,14-DIHYDRO-PGF2α DERIVATIVES

Invention relates to the process for preparation of 13,14-dihydro-PGF2α derivatives of R or S configuration at carbon atom in omega chain substituted by hydroxyl, represented by formula (I), wherein the meaning of substituents is defined in the description. Compounds (I) are valuable biologically active substances or intermediates thereof. The invention especially relates to the process for preparation of 13,14-dihydro-15(R)-17-substituted-18,19,20-trinor-PGF2α, ie. latanoprost.