616866-44-5

Basic information

• Product Name: D-Aspartic acid, N-[(4-methylphenyl)sulfonyl]-, dimethyl ester
• CAS NO: 616866-44-5
• Molecular Formula: C13H17NO6S
• Molecular Weight: 315.347
• Mol File: 616866-44-5.mol

Chemical Properties

• CAS DataBase Reference: D-Aspartic acid, N-[(4-methylphenyl)sulfonyl]-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: D-Aspartic acid, N-[(4-methylphenyl)sulfonyl]-, dimethyl ester(616866-44-5)
• EPA Substance Registry System: D-Aspartic acid, N-[(4-methylphenyl)sulfonyl]-, dimethyl ester(616866-44-5)

Safety Data

• Hazardous Substances Data: 616866-44-5(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 1783-96-6 (2R)-aspartic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 14358-33-9 dimethyl (R)-2-aminobutanedioate hydrochloride 
• 6384-18-5 dimethyl D-aspartate 

Downstream Products

• 934472-06-7 2-hydroxyethyl-1-(toluene-4-sulfonyl)aziridine 
• 1334404-52-2 2-allyl-6-(2-hydroxyethyl)-1-(toluene-4-sulfonyl)-piperidin-3-ol 
• 1334404-51-1 2-allyl-6-[2-((tert-butyl)diphenylsilanyloxy)ethyl]-1-(toluene-4-sulfonyl)-piperidin-3-ol 
• 1334404-53-3 (-)-(1R,3S,6S)-3-(2-((tert-butyl)diphenylsilyloxy)ethyl)-2-tosyl-2-azabicyclo[4.1.0]heptane 
• 1334404-54-4 (+)-(1S,2R,5S)-2-bromo-2-(bromomethyl)-9-tosyl-8-oxa-9-aza-bicyclo[3.3.1]nonane 
• 1334404-55-5 (-)-2-((1R,3S,6S)-2-tosyl-2-azabicyclo[4.1.0]heptan-3-yl)ethanol 
• 1334404-56-6 (2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-(iodomethyl)-2-methoxy-1-tosylpiperidine 
• 1334404-58-8 (-)-(E)-methyl 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)but-2-enoate 
• 1334404-60-2 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)butan-1-ol 
• 1334404-41-9 C₃₁H₄₁NO₄SSi 
• 1334404-44-2 (R)-N-(1-[2-((tert-butyl)diphenylsilanyloxy)ethyl]-4-[1,3]dioxolan-2-ylbutyl)-4-methylbenzenesulfonamide 
• 1334404-42-0 2-(((tert-butyl)diphenylsilanoxy)ethyl)-5-methylene-1-(toluene-4-sulfonyl)piperidine 
• 1334404-45-3 2-[2-((tert-butyl)diphenylsilanyloxy)ethyl]-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine 
• 1334404-49-7 8-methyl-9-(toluene-4-sulfonyl)-2-oxa-9-azabicyclo[3.3.1]nonane 

Relevant articles and documents

A Stereoselective Formal Synthesis of Quinolizidine (–)-217A

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Stereoselective approaches to 2,3,6-trisubstituted piperidines. An enantiospecific synthesis of quinolizidine (-)-217A

The enantiospecific and diastereocontrolled total synthesis of alkaloid (-)-217A is described that employs a stepwise [3+3] annelation strategy and a piperidine 2,3-cyclopropanation-ring opening reaction as the key steps.

An efficient approach to 2-substituted N-tosylpiperdines: asymmetric synthesis of 2-(2-hydroxy substituted)piperidine alkaloids

We have developed an efficient and a general approach to chiral 2-substituted N-tosylpiperidines starting from chiral α-substituted-N-tosylaziridines. Using this approach, we have synthesized (+)-coniine. The synthesis of chiral N-tosyl-2-piperidinylethanol 15 and ent-15, was achieved from l- and d-aspartic acids, respectively in few steps. Piperidine 15 was converted into 2-(2-hydroxysubstituted)piperidines of type 2 in optically active form. By applying this strategy, asymmetric syntheses of halosaline (R,R)-2a, (+)- and (-)-sedamine 2b, (+)- and (-)-allosedamine 2c, (+)- and (-)-sedridine 2d, (+)- and (-)-allosedridine 2e, (+)-tetraponerine T-3 3a, T-4 3c, T-7 3b, and T-8 3d have been achieved in high yields. These stereoisomers can be interconverted via Mitsunobu inversion in excellent yields.

Development of a flexible approach to Nuphar alkaloids via two enantiospecific piperidine-forming reactions

(Chemical Equation Presented). In this paper we describe the stereoselective synthesis of functionalized lactam 7 via two enantiospecific piperidine-forming techniques and its employment in a general synthetic approach to Nuphar alkaloids. Specifically, the formation of piperidine 18 by formal [3 + 3] cycloaddition and stepwise annelation processes is described; the latter technique was found to be significantly more efficient than the Pd-catalyzed TMM addition process. Finally, exploitation of the exocyclic alkene installed in the piperidine-forming reaction in the transformation of 18 to (-)-deoxynupharidine ((-)-2), (-)-castoramine ((-)-3), and (-)-nupharolutine ((-)-4) via intermediate lactam 7 is delineated.

A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (-)-Deoxynupharidine

(Equation presented) A stereocontrolled route to Nuphar alkaloids is described that employs a formal [3 + 3] cycloaddition strategy to assemble the piperidine nucleus. The addition of Pd-TMM complexes to aziridine 10 was found to be sluggish; however, the addition of a functionalized allyl Grignard reagent followed by a Mitsunobu condensation reaction provided 11 in high yield. The employment of this route in the formal synthesis of (-)-deoxynupharidine 1 is described.