125664-95-1

Basic information

• Product Name: N-PROPIONYL-(2R)-BORNANE- 10,2-SULTAM
• Synonyms: N-PROPIONYL-(2R)-BORNANE- 10,2-SULTAM;1-((3aS,6R,7aR)-8,8-DiMethyl-2,2-dioxidohexahydro-1H-3a,6-Methanobenzo[c]isothiazol-1-yl)propan-1-one;(R)-(-)-Propionyl-2,10-camphorsultam
• CAS NO: 125664-95-1
• Molecular Formula: C₁₃H₂₁NO₃S
• Molecular Weight: 271.38
• Product Categories: Peptide
• Mol File: 125664-95-1.mol

Chemical Properties

• Melting Point: 153-154 °C(Solv: methanol (67-56-1))
• Boiling Point: 384.8±25.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -14.14±0.40(Predicted)
• CAS DataBase Reference: N-PROPIONYL-(2R)-BORNANE- 10,2-SULTAM(CAS DataBase Reference)
• NIST Chemistry Reference: N-PROPIONYL-(2R)-BORNANE- 10,2-SULTAM(125664-95-1)
• EPA Substance Registry System: N-PROPIONYL-(2R)-BORNANE- 10,2-SULTAM(125664-95-1)

Safety Data

• Hazardous Substances Data: 125664-95-1(Hazardous Substances Data)

Usage

Uses

As the provided materials do not specify the uses of N-Propionyl-(2R)-bornane-10,2-sultam, it is not possible to list its applications based on the information given. However, given its classification as a bicyclic monoterpenoid, it can be inferred that it may be used in chemical research for the synthesis of other compounds or as a starting material in the development of new chemical entities. Further research and data would be required to confirm its specific applications in various industries.

Upstream product

• 79-03-8 propionyl chloride 
• 94594-90-8 (2R)-bornane-10,2-sultam 
• 123-62-6 propionic acid anhydride 
• 125664-99-5 N-<(2R,3S)-3-hydroxy-2-methylbutanoyl>bornane-10,2-sultam 
• 220170-24-1 C₈H₁₄O₃ 

Downstream Products

• 127392-90-9 [(S)-3-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-3-oxo-propyl]-methyl-carbamic acid benzyl ester 
• 1228007-30-4 N-[(2S,3S)-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylpentanoyl]-bornane-10,2-sultam 
• 133391-78-3 (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-chloro-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-propan-1-one 
• 133391-78-3 (2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-chloro-phenyl)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-propan-1-one 
• 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 
• 1027311-89-2 (2R,3S)-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2-methylheptan-1-one 
• 125665-04-5 (S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-((R)-hydroxy-phenyl-methyl)-butan-1-one 
• 125665-04-5 N-<(2S,3S)-2-(hydroxybenzyl)butanoyl>bornane-10,2-sultam 
• 125665-04-5 N-<(2R,3R)-2-(hydroxybenzyl)butanoyl>bornane-10,2-sultam 
• 125665-04-5 (R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-((S)-hydroxy-phenyl-methyl)-butan-1-one 
• 125665-15-8 (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-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-(4-methoxy-phenyl)-2-methyl-propan-1-one 
• 125685-29-2 (R)-2-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-hexan-1-one 
• 125665-18-1 (R)-2-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-butan-1-one 
• 125665-07-8 N-<(2R,3R)-2-(hydroxybenzyl)hexanoyl>bornane-10,2-sultam 

Relevant articles and documents

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.

Diastereoselective synthesis of a lilac aldehyde isomer and its electrophysiological detection by a moth

The monoterpene lilac aldehyde (=2-(5-ethenyl-5-methyloxolan-2-yl)propanal) is a widespread flower scent. Lilac aldehyde is emitted in high amounts from nocturnal plant species, and it is highly attractive to nocturnal moth pollinators, such as Hadena bicruris, the pollinating seed predator of Silene latifolia. Lilac aldehyde possesses three stereogenic centers and can occur in eight stereoisomers which induce different antennal responses in H. bicruris. The distribution pattern of stereoisomers differs among plant species, and if H. bicruris has different receptors for detecting different isomers, it may use these differences to discriminate flowers of S. latifolia hosts from flowers of non-host plants. To investigate the question whether the moths have in their antennae one olfactory receptor or several different receptors for the detection of the single lilac aldehyde isomers, (2S,2′S,5′S)-lilac aldehyde was diastereoselectively synthesized. (2S,2′S,5′S)-Lilac aldehyde and its isomeric mixture were tested electrophysiologically on antennae of H. bicruris. The results displayed antennal responses, which are characteristic for a single receptor that detects the different lilac aldehyde isomers. Copyright

Diastereoselective synthesis of the C14-C29 fragment of amphidinol 3

An efficient stereoselective synthesis of the C14-C29 fragment highlighting a coupling reaction between a 1,3-dithiane derivative and an α-branched aldehyde was realized. This highly convergent synthesis involved two chiral pools, l-malic acid and (+)-camphorsulfonic acid, which are the starting compounds to control the six stereogenic centers present in the C14-C29 fragment of amphidinol 3.

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.

Synthesis of enantiomerically pure divinyl- and diallylcarbinols

Acylated oxazolidinones and bornane sultams can be cleaved to divinyl- and diallylcarbinols by treatment with vinyl- or allylmetal compounds. For the preparation of divinylcarbinols, acylated bornane sultams are the starting materials of choice, while for the preparation of diallylcarbinols acylated oxazolidinones and bornane sultams work equally well.

Bornanesultam-directed asymmetric synthesis of crystalline, enantiomerically pure syn aldols

N-acylsultams 2 furnish, via aldolization of their enolates 16 with aldehydes, diastereomerically pure, crystalline syn aldols. The absolute configuration of the product is controlled by the choice of the enolate counterion: 16, M = B → 3; 16, M = Li or S