104901-62-4

Basic information

• Product Name: 6^A,6^B-Di-O-(p-tosyl)-γ-cyclodextrin
• Synonyms: 6^A,6^B-Di-O-(p-tosyl)-γ-cyclodextrin
• CAS NO: 104901-62-4
• Molecular Weight: 1605.52
• Mol File: 104901-62-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 6^A,6^B-Di-O-(p-tosyl)-γ-cyclodextrin(CAS DataBase Reference)
• NIST Chemistry Reference: 6^A,6^B-Di-O-(p-tosyl)-γ-cyclodextrin(104901-62-4)
• EPA Substance Registry System: 6^A,6^B-Di-O-(p-tosyl)-γ-cyclodextrin(104901-62-4)

Safety Data

• Hazardous Substances Data: 104901-62-4(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 17465-86-0 cyclomaltooctaose 
• 17465-86-0 γ-cyclodextrin 

Downstream Products

• 923262-92-4 6^A-(N-dansyl-L-cysteine)-6^H-tosyl-γ-cyclodextrin 

Relevant articles and documents

Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by capped γ-cyclodextrins: Critical control of enantioselectivity by cap rigidity

(Graph Presented) A series of γ-cyclodextrins (CDs) modified with capping and noncapping aromatic group(s) were synthesized to mediate the enantiodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylic acid (AC). The complexation behavior of these γ-CDs with AC was studied by circular dichroism, UV-vis, and NMR spectroscopy to reveal the formation of stable 1:2 host-guest complexes in all cases. The capped γ-CD with a biphenyl group bridging the A and D glucose units was shown to confine the included AC molecules most strictly among the capped and noncapped γ-CDs examined. Photocyclodimerization of AC mediated by capped γ-CDs considerably improved the yield and enantiomeric excess (ee) of the head-to-head photodimer 3. The ee and the absolute configuration of syn-head-to-tail photodimer 2 critically depended on the rigidity of capping. Thus, the flexibly capped and rim-substituted γ-CDs afforded 2 in moderate ee's of around 40%, whereas γ-CD with a rigid biphenyl cap gave the antipodal 2 in -58% ee. Interestingly, the ee of 2 mediated by flexibly capped γ-CDs was highly sensitive to the temperature variation as a consequence of large differential entropy changes in the enantiodifferentiation process. In contrast, the entropy effect does not appear to play a significant role in the photocyclodimerization of AC with rigidly capped γ-CDs. The differential enthalpy and entropy changes obtained for the enantiodifferentiating photocyclodimerization mediated by native and most of the modified γ-CDs gave an excellent enthalpy-entropy compensation plot with an exception of the biphenyl-capped γ-CD, indicating the operation of significantly different enantiodifferentiation mechanism within the rigidly capped cyclodextrin cavity.

Synthesis of 6A,6X-Di-O-(p-tosyl)-γ-cyclodextrins and Their Structural Determination through Enzymatic Hydrolysis of 3A,6A;3X,6X-Dianhydro-γ-cyclodextrins

6A,6X-Di-O-(p-tosyl)-γ-cyclodextrins (X = B, C, D, and E) were prepared by the reaction of γ-cyclodextrin and p-tosyl chloride in pyridine and isolated by reversed-phase column chromatography.From the results of Taka amylolyses of 3A,6A;3X,6X-dianhydro-γ-cyclodextrins which were obtained from the corresponding ditosylates, the regiochemistry of the ditosylates was determined.