141993-16-0

Basic information

• Product Name: N-ACETYL-(2S)-BORNANE 10,2-SULTAM
• Synonyms: (N-ACETYL)-(2R)-BORNANE-10,2-SULTAM;N-ACETYL-(2S)-BORNANE 10,2-SULTAM;(N-Acetyl)-(2R)-bornane-102-sultame;1-((3aS,6R,7aR)-8,8-diMethyl-2,2-dioxidohexahydro-1H-3a,6-Methanobenzo[c]isothiazol-1-yl)ethanone;(R)-(-)-Acetyl-2,10-camphorsultam
• CAS NO: 141993-16-0
• Molecular Formula: C₁₂H₁₉NO₃S
• Molecular Weight: 257.35
• Product Categories: Peptide
• Mol File: 141993-16-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 371.4°C at 760 mmHg
• Flash Point: 178.4°C
• Appearance: /
• Density: 1.1945 (rough estimate)
• Vapor Pressure: 1.03E-05mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-ACETYL-(2S)-BORNANE 10,2-SULTAM(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYL-(2S)-BORNANE 10,2-SULTAM(141993-16-0)
• EPA Substance Registry System: N-ACETYL-(2S)-BORNANE 10,2-SULTAM(141993-16-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• Hazardous Substances Data: 141993-16-0(Hazardous Substances Data)

Usage

General Description

N-Acetyl-(2S)-bornane 10,2-sultam, also known as N-acetyl-2-oxobornanesultam, is a chemical compound derived from the bicyclic monoterpene known as camphor. It is a white crystalline powder that is soluble in organic solvents and insoluble in water. N-ACETYL-(2S)-BORNANE 10,2-SULTAM is commonly used as a reagent in organic synthesis to produce various pharmaceuticals and other chemical products. Its unique molecular structure and reactivity make it a valuable tool in the production of complex organic compounds. Additionally, it has been investigated for its potential applications in the field of asymmetric catalysis and as a chiral auxiliary in organic synthesis.

InChI:InChI=1/C12H19NO3S/c1-8(14)13-10-6-9-4-5-12(10,11(9,2)3)7-17(13,15)16/h9-10H,4-7H2,1-3H3/t9-,10-,12-/m0/s1

Upstream product

• 167934-73-8 N-trimethylsilylbornane-10,2-sultam 
• 60886-80-8 (1S)-(-)-camphorsulfonylimine 
• 21286-54-4 Camphorsulfonyl chloride 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 108448-77-7 (+)-camphorsultam 
• 75-36-5 acetyl chloride 
• 7137-32-8 acetic pivalic mixed anhydride 
• 94594-90-8 (2R)-bornane-10,2-sultam 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 246167-29-3 N-((14S)-14-hydroxy-14-allyl)acetyloyl-(2R)-bornane-10,2-sultam 

Downstream Products

• 142037-68-1 (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)-3-hydroxy-3-phenyl-propan-1-one 
• 141993-18-2 (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)-3-hydroxy-3-phenyl-propan-1-one 
• 141993-23-9 (R)-3-Cyclohexyl-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-hydroxy-propan-1-one 
• 141993-23-9 (S)-3-Cyclohexyl-1-((1S,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-propan-1-one 
• 94668-55-0 (1S)-N-crotyl-2,10-camphorsultam 
• 398477-90-2 (2R)-N-[(3R)-5-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)pentanoyl]bornane-10,2-sultam 

Relevant articles and documents

MANGANESE(III)-PROMOTED OXIDATIVE FREE-RADICAL CYCLIZATIONS OF β-KETO IMIDES: ASYMMETRIC INDUCTION WITH OPPOLZER'S CHIRAL SULTAM

Oxidative free-radical cyclization of the unsaturated β-keto imide 3 containing Oppolzer's D-camphor sultam as a chiral auxiliary was studied.Intramolecularly promoted oxidative free-radical cyclization of 3 with Mn(III) in the presence of Cu(II) produced the stereoisomeric cis-hydrindanones 4 and 5 in a 3:1 ratio at 25 deg C.

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.

Total syntheses of epothilones B and D

A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12-C13, Wadsworth-Emmons olefination of methyl ketone 28 with the phosphonate ester 8, diastereoselective aldol condensation of aldehyde 5 with the enolate of keto acid derivatives to form the C6-C7 bond, selective deprotection of acid 52, and macrolactonization.

The total synthesis and biological assessment of trans-epothilone A

The total synthesis of (12S,13S)-trans-epothilone A (1a) was achieved based on two different convergent strategies. In a first-generation approach, construction of the C(11)-C(12) bond by Pd0-catalyzed Negishi-type coupling between the C(12)-to-C(15) trans-vinyl iodide 5 and the C(7)-to-C(11) alkyl iodide 4 preceded the (nonselective) formation of the C(6)-C(7) bond by aldol reaction between the C(7)-to-C(15) aldehyde 25 and the dianion derived from the C(1)-to-C(6) acid 3. The lack of selectivity in the aldol step was addressed in a second-generation approach, which involved construction of the C(6)-C(7) bond in a highly diastereoselective fashion through reaction between the acetonide-protected C(l)-to-C(6) diol 31 ('Schinzer's ketone') and the C(7)-to-C(11) aldehyde 30. As part of this strategy, the C(11)-C(12) bond was established subsequent to the critical aldol step and was based on B-alkyl Suzuki coupling between the C(1)-to-C(11) fragment 40 and C(12)-to-C(15) trans-vinyl iodide 5. Both approaches converged at the stage of the 3-O, 7-O-bis-TBS-protected seco acid 27, which was converted to trans-deoxyepothilone A (2) via Yamaguchi macrolactonization and subsequent deprotection. Stereoselective epoxidation of the trans C(12)-C(13) bond could be achieved by epoxidation with Oxone in the presence of the catalyst 1,2:4,5-di-O-isopropylidene-L-erythro-2,3-hexodiuro-2,6-pyranose (42a), which provided a 8:1 mixture of 1a and its (12R,13R)-epoxide isomer 1b in 27% yield (54% based on recovered starting material). The absolute configuration of 1a was established by X-ray crystallography. Compound 1a is at least equipotent with natural epothilone A in its ability to induce tubulin polymerization and to inhibit the growth of human cancer cell lines in vitro. In contrast, the biological activity of 1b is at least two orders of magnitude lower than that of epothilone A or 1a.