32860-56-3

Basic information

• Product Name: MONO-6-O-(P-TOLUENESULFONYL)-ALPHA-CYCLODEXTRIN
• Synonyms: MONO-6-O-(P-TOLUENESULFONYL)-ALPHA-CYCLODEXTRIN;Mono-6-O-Tosyl-alpha-Cyclodextrin;Mono-6-O-(p-toluenesulfonyl)-α-cyclodextrin;Mono-6-O-a-D-glucosyl a-cyclodextrin;Mono-6-O-(p-toluenesulfonyl)-&alpha
• CAS NO: 32860-56-3
• Molecular Formula: C₄₃H₆₆O₃₂S
• Molecular Weight: 1127.03
• Product Categories: Cyclodextrins;Functional Materials;Macrocycles for Host-Guest Chemistry
• Mol File: 32860-56-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 221-225 ºC
• Boiling Point: 1454.324 °C at 760 mmHg
• Flash Point: 833.345 °C
• Appearance: /
• Density: 1.586
• Refractive Index: 1.593
• Water Solubility: Soluble in water
• CAS DataBase Reference: MONO-6-O-(P-TOLUENESULFONYL)-ALPHA-CYCLODEXTRIN(CAS DataBase Reference)
• NIST Chemistry Reference: MONO-6-O-(P-TOLUENESULFONYL)-ALPHA-CYCLODEXTRIN(32860-56-3)
• EPA Substance Registry System: MONO-6-O-(P-TOLUENESULFONYL)-ALPHA-CYCLODEXTRIN(32860-56-3)

Safety Data

• Hazardous Substances Data: 32860-56-3(Hazardous Substances Data)

Usage

Description

MONO-6-O-(P-TOLUENESULFONYL)-ALPHA-CYCLODEXTRIN, with the CAS number 32860-56-3, is a carbohydrate derivative of alpha-cyclodextrin. It is characterized by its p-toluenesulfonyl group at the 6-O position, which imparts unique chemical properties to the molecule. MONO-6-O-(P-TOLUENESULFONYL)-ALPHA-CYCLODEXTRIN is known for its high aqueous solubility, with a solubility of 88.5g/100mL, making it a versatile compound for various applications.

Uses

Used in Pharmaceutical Industry:
MONO-6-O-(P-TOLUENESULFONYL)-ALPHA-CYCLODEXTRIN is used as a key intermediate in the synthesis of pentacyclic triterpene α-cyclodextrin conjugates. These conjugates serve as HCV (Hepatitis C Virus) entry inhibitors, playing a crucial role in the development of antiviral drugs to combat Hepatitis C.
Used in Chemical Synthesis:
Due to its unique chemical properties, MONO-6-O-(P-TOLUENESULFONYL)-ALPHA-CYCLODEXTRIN can be employed as a building block in the synthesis of various complex organic molecules. Its p-toluenesulfonyl group can be used for further functionalization and modification, making it a valuable compound in organic chemistry and drug development.
Used in Supramolecular Chemistry:
The high aqueous solubility and unique structure of MONO-6-O-(P-TOLUENESULFONYL)-ALPHA-CYCLODEXTRIN make it an attractive candidate for supramolecular chemistry applications. It can be used to study host-guest interactions, molecular recognition, and the formation of non-covalent complexes with various guest molecules.
Used in Material Science:
The unique properties of MONO-6-O-(P-TOLUENESULFONYL)-ALPHA-CYCLODEXTRIN can also be exploited in the development of novel materials with specific properties. For example, it can be used to create stimuli-responsive materials, self-assembling systems, or as a component in the design of advanced drug delivery systems.

InChI:InChI=1/C43H66O32S/c1-12-2-4-13(5-3-12)76(61,62)63-11-19-37-25(54)31(60)43(69-19)74-36-18(10-48)67-41(29(58)23(36)52)72-34-16(8-46)65-39(27(56)21(34)50)70-32-14(6-44)64-38(26(55)20(32)49)71-33-15(7-45)66-40(28(57)22(33)51)73-35-17(9-47)68-42(75-37)30(59)24(35)53/h2-5,14-60H,6-11H2,1H3/t14?,15?,16?,17?,18?,19?,20?,21?,22?,23?,24?,25?,26-,27-,28-,29-,30-,31-,32+,33+,34+,35+,36+,37+,38+,39+,40+,41+,42+,43+/m0/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 10016-20-3 alpha cyclodextrin 

Downstream Products

• 29556-37-4 6-deoxy-6-amino-α-cyclodextrin 
• 94789-62-5 6-O-monotosyl permethylated α-cyclodextrin 

Relevant articles and documents

Application of host-guest chemistry in nanotube-based device fabrication: Photochemically controlled immobilization of azobenzene nanotubes on patterned α-CD monolayer/Au substrates via molecular recognition

Azobenzene-functionalized nanotubes recognized and attached onto well-defined complementary regions of thiolated α-CD SAM/Au substrates via host-guest molecular recognition. The binding between the azobenzene nanotubes and the α-CD SAM/Au substrates was c

CONVENIENT PREPARATION AND EFFECTIVE SEPARATION OF THE C-2 AND C-3 TOSYLATES OF α-CYCLODEXTRIN

Secondary tosylates of α-cyclodextrin were conveniently prepared by the reaction of the cyclodextrin with tosyl chloride in alkaline water where pH of the mixture should be allowed to decrease as the proceeding of reaction, and were effectivelly separated by reversed-phase column chromatography.

Unraveling unidirectional threading of α-cyclodextrin in a [2]rotaxane through spin labeling approach

We present here the results of a CW-ESR investigation of a double spin labeled α-cyclodextrin-based [2]rotaxane that is characterized by the presence of nitroxide labels both at the wheel and at the dumbbell. This was accomplished by synthesizing a spin l

Synthesis and biological evaluation of multivalent carbohydrate ligands obtained by click assembly of pseudo-rotaxanes

Multivalent carbohydrate ligands have been prepared by assembling α-cyclodextrin-based pseudo-rotaxanes through "click chemistry". The inclusion complex formed by a lactosyl-α-CD conjugate and a decane axle carrying a lactosyl stopper at one extremity and

Enhanced single-isomer separation and pseudoenantiomer resolution of new primary rim heterobifunctionalized α-cyclodextrin derivatives

The synthesis of batch-to-batch reproducible cyclodextrin (CD) derivatives often requires functionalization at specific positions of the CD skeleton. However, the regioselective preparation of this type of CD derivatives remains a challenge in synthetic c

A manganese porphyrin-α-cyclodextrin conjugate as an artificial enzyme for the catalytic epoxidation of polybutadiene

We describe a manganese porphyrin-α-cyclodextrin conjugate as a catalyst for the epoxidation of cis-polybutadiene with trans-epoxide preference, which is a reverse stereoselectivity as compared to normal porphyrin catalysts. A clamp-like mechanism is prop