94594-90-8

Usage

Uses

Used in Organic Synthesis:
(2R)-Bornane-10,2-sultam is used as a reagent for the preparation of Camphorsultam conjugates, which are essential in various organic synthesis processes.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, (2R)-Bornane-10,2-sultam is used as a proton source in the synthesis of chiral α,γ-substituted γ-butyrolactones. It is also employed in the asymmetric synthesis of (S)and (R)-N-Fmoc-S-trityl-α-methylcysteine, a crucial component in peptide synthesis.
Used as a Chiral Probe:
(2R)-Bornane-10,2-sultam serves as a chiral probe for optical resolution by High-Performance Liquid Chromatography (HPLC) and X-ray crystallographic determination of the absolute stereochemistry of carboxylic acids. This application is vital in the analysis and separation of enantiomers, which are essential in various industries, including pharmaceuticals and agrochemicals.
Used in Dienophile Preparation:
(2R)-Bornane-10,2-sultam is also used to prepare N-acryloyl derivatives, which are employed as dienophiles in asymmetric Diels-Alder reactions. These reactions are crucial in the synthesis of complex organic molecules with specific stereochemistry.
Overall, (2R)-Bornane-10,2-sultam is a versatile reagent with applications in various fields of organic chemistry, including asymmetric synthesis, chiral probe applications, and the preparation of intermediates for complex organic molecules. Its unique properties make it an essential component in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C10H17NO2S/c1-9(2)7-3-4-10(9)6-14(12,13)11-8(10)5-7/h7-8,11H,3-6H2,1-2H3/t7-,8-,10+/m0/s1

Upstream product

• 60886-80-8 (1S)-(-)-camphorsulfonylimine 
• 186581-53-3 diazomethane 
• 125664-99-5 N-<(2R,3S)-3-hydroxy-2-methylbutanoyl>bornane-10,2-sultam 
• 125665-01-2 N-<(2R,3S)-3-hydroxy-2,4-dimethylpentanoyl>bornane-10,2-sultam 
• 125760-65-8 N-<(2S,3R)-3-hydroxy-2,4-dimethylpentanoyl>bornane-10,2-sultam 
• 125665-08-9 N-<(2S,3R)-3-hydroxy-2-methylhexenoyl>bornane-10,2-sultam 
• 125665-06-7 N-<(2S,3R)-2-ethyl-3-hydroxy-4-methylpentanoyl>bornane-10,2-sultam 
• 125665-02-3 N-<(2S,3R)-2-methyl-3-hydroxy-(E)-4-hexenoyl>bornane-10,2-sultam 
• 125665-09-0 N-<(2S,3R)-2-ethyl-3-hydroxy-(E)-hexenoyl>bornane-10,2-sultam 
• 125664-98-4 (2R,3R)-1-((6R)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-3-hydroxy-2-methyl-3-phenylpropan-1-one 
• 125760-63-6 N-<(2S,3R)-2-methyl-3-hydroxy-3-phenylpropanoyl>bornane-10,2-sultam 
• 125665-04-5 N-<(2R,3R)-2-(hydroxybenzyl)butanoyl>bornane-10,2-sultam 
• 125665-04-5 N-<(2S,3S)-2-(hydroxybenzyl)butanoyl>bornane-10,2-sultam 
• 64-17-5 ethanol 

Downstream Products

• 94668-55-0 (1S)-N-crotyl-2,10-camphorsultam 
• 121560-18-7 (3aS,6R,7aR)-1-(cyclohex-1-en-1-ylcarbonyl)-8,8-dimethylhexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 
• 157518-33-7 4-[(E)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-oxo-propenyl]-benzonitrile 
• 157604-00-7 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(3-methoxy-phenyl)-propenone 
• 116195-24-5 (2-methyl-3-phenyl-butanoyl)bornane-10,2-sultam 
• 138566-17-3 2-(benzhydrylideneamino)-1-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1.5]dec-4-yl)ethanone 
• 125664-95-1 N-propionyl-(2R)-bornane-(10,2)-sultam 
• 141993-16-0 1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.0^1.5]dec-4-yl]-ethanone 
• 157603-99-1 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(2-methoxy-phenyl)-propenone 
• 121560-17-6 N-<(E)-2-methyl-3-phenyl-2-propenoyl>bornane-10,2-sultam 
• 109053-73-8 (3aS,6R,7aR)-8,8-dimethyl-1-[(2E)-3-phenylprop-2-enoyl]hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 
• 157604-01-8 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(3,4,5-trimethoxy-phenyl)-propenone 
• 157604-02-9 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(5-fluoro-2-methoxy-phenyl)-propenone 
• 157604-03-0 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-[2-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-propenone 

Relevant academic research and scientific papers

Palladium-Catalyzed Stereoselective Cyclization of in Situ Formed Allenyl Hemiacetals: Synthesis of Rosuvastatin and Pitavastatin

A diastereoselective palladium-catalyzed cyclization of allenyl hemiacetals is described. It permits the selective synthesis of 1,3-dioxane derivatives, precursors for syn-configured 1,3-diols which make an appearance in all of the statin representatives. The reaction allows the total synthesis of Rosuvastatin and Pitavastatin in a straightforward fashion.

Stereoselective α-Hydroxylation of Amides Using Oppolzer's Sultam as Chiral Auxiliary

An Oppolzer's sultam-based highly stereoselective α-hydroxylation of amides was developed to deliver the desired products in good yield and excellent diastereoselectivity (>20/1). The generally crystalline products and the recyclability of the chiral auxiliary illustrate the practicability and scalability of the current approach.

Tosvinyl and besvinyl as protecting groups of imides, azinones, nucleosides, sultams, and lactams. Catalytic conjugate additions to tosylacetylene

The use of the 2-(4-methylphenylsulfonyl)-ethenyl (tosvinyl, Tsv) group for the protection of the NH group of a series of imides, azinones (including AZT), inosines, and cyclic sulfonamides has been examined. The Tsvprotected derivatives are obtained in excellent yields by conjugate addition to tosylacetylene (ethynyl p-tolyl sulfone). The stereochemistry of the double bond can be controlled at will: with only 1 mol % of Et3N or with catalytic amounts of NaH, the Z stereoisomers are generated almost exclusively, while the E isomers are obtained using a stoichiometric amount of DMAP. Analogous phenylsulfonylvinyl-protected groups (with the besvinyl or Bsv group instead of Tsv) are obtained stereospecifically by reaction with (Z)- or (E)-bis(phenylsulfonyl)ethene. For lactams and oxazolidinones, this last method is much better. The Tsv and Bsv groups are stable in the presence of non-nucleophilic bases and to acids. They can be removed highly effectively via a conjugate addition-elimination mechanism using pyrrolidine or sodium dodecanethiolate as nucleophiles.

Amphidinolide B: Total synthesis, structural investigation, and biological evaluation

The total syntheses of amphidinolide B1 and the proposed structure of amphidinolide B2 have been accomplished. Key aspects of this work include the development of a practical, non-transition-metal-mediated method for the construction of the C13-C15 diene, the identification of α-chelation and dipole minimization models for diastereoselective methyl ketone aldol reactions, the discovery of a spontaneous Horner-Wadsworth-Emmons macrocyclization strategy, and the development of a novel late stage method for construction of an allylic epoxide moiety. The originally proposed structure for amphidinolide B2 and diastereomers thereof display potent antitumor activities with IC50 values ranging from 3.3 to 94.5 nM against human solid and blood tumor cells. Of the different stereoisomers, the proposed structure of amphidinolide B2 is over 12-fold more potent than the C8,9-epimer and C18-epimer in human DU145 prostate cancer cells. These data suggest that the epoxide stereochemistry is a significant factor for anticancer activity.

A facile, inexpensive and scalable route to thiol-protected α-methyl cysteine

A facile, scalable synthesis of α-methyl cysteine with three alternate thiol protecting groups (trityl, allyl and tert-butyl) is described. The thiol-protected amino acids are obtained in six steps from l-cysteine ethyl ester and are ideally suited for a range of natural product and solid-phase peptide synthesis applications. Georg Thieme Verlag Stuttgart - New York.

Stereoselective synthesis of (3S,5S,6S)-tetrahydro-6-isopropyl-3,5- dimethylpyran-2-one; A C5-epimer of a component of a natural sex pheromone of the wasp Macrocentrus grandii, the larval parasitoid of the European corn borer Ostrinia nubilalis

(3S,5S,6S)-Tetrahydro-6-isopropyl-3,5-dimethylpyran-2-one, a C5-epimer of a component of the natural sex pheromone of the wasp Macrocentrus grandii, the larval parasitoid of the European corn borer Ostrinia nubilalis, was synthesized starting from methyl l-valinate. The transformation includes a Kulinkovich cyclopropanation reaction, a cationic cyclopropyl-allyl rearrangement of cyclopropyl methanesulfonate, a diastereoselective alkylation of Oppolzer's (N-propionyl)-(2R)-bornane-10,2-sultam and a diastereoselective hydrogenation using Wilkinson's catalyst as the key steps.

Efficacious preparation of Oppolzer's glycylsultam via the Delepine reaction

A new preparative route to Oppolzer's glycylsultam, the 'NC' component in the asymmetric [C+NC+CC] coupling reaction leading to functionalized pyrrolidines, is described. The synthesis features a novel application of the Delepine reaction, providing a saf

Process for Production of Optically Active Carboxlic Acid Compound

An optically active acylated camphorsultam can be hydrolyzed with an aqueous solution of an alkaline earth metal hydroxide in the presence of a branched alkanol, to give a corresponding optically active carboxylic acid compound in safely and inexpensively

Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: Synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl- 4-butanolide

The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4- butanolide 13 is presented.