74761-34-5

Upstream product

• 652990-14-2 1′,2,2′,3,3′,4,4′-hexa-O-benzyl-6,6′-dideoxy-6,6′-di-chlorosucrose 
• 1206803-50-0 1,3,4-tri-O-benzyl-6-O-triethyl-silyl-β-D-fructofuranosyl 2,3,4-tri-O-benzyl-6-O-triethyl-silyl-α-D-glucopyranoside 
• 63775-77-9 6,6'-di-O-(tert-butyldimethylsilyl)saccharose 
• 57-50-1 Sucrose 
• 100-39-0 benzyl bromide 
• 392699-44-4 6-O-acetyl-1,3,4-tri-O-benzyl-β-D-fructofuranosyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 392699-42-2 2,3,3',4,4'-hexa-O-benzyl-6,6'-O-ethoxyethylenesucrose 
• 392699-41-1 2,3,3',4,4'-hexa-O-benzyl-6,6'-O-diethoxyethylenesucrose 
• 652990-17-5 (1R,3S,4S,5R,6R,12R,13R,19R,20R,21S,22R)-4,5,20,21,22-Pentakis-benzyloxy-3-benzyloxymethyl-12,13-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,8,11,14,17,23,24-heptaoxa-tricyclo[17.3.1.1^3,6]tetracosane 
• 652990-15-3 1',2,3,3',4,4'-hexa-O-benzyl-6,6'-O-(3,6,9-trioxaundecan-1,11-diyl)sucrose 
• 652990-16-4 C₆₄H₆₈O₁₃ 
• 652990-18-6 1',2,3,3',4,4'-hexa-O-benzyl-6,6'-di-O-(pent-4-enoyl)sucrose 
• 652990-21-1 1',2,3,3',4,4'-hexa-O-benzyl-6,6'-di-O-mesylsucrose 
• 865200-99-3 [(2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-tert-butoxycarbonylmethoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-ylmethoxy]-acetic acid tert-butyl ester 
• 865201-03-2 C₆₈H₇₆O₁₅ 
• 865201-01-0 1',2,3,3',4,4'-hexa-O-benzyl-6,6'-O-(5,5-dimethyl-3,7-dioxanonan-1,9-diyl)-sucrose 
• 900525-69-1 1',2,3,3',4,4'-hexa-O-benzyl-6'-O-tert-butyldimethylsilylsucrose 
• 900525-72-6 6’-O-tert-butyldiphenylsilyl-1’,2,3,3’,4,4’-hexa-O-benzylsucrose 
• 1186624-89-4 6-O-(cyanomethyl)-1',2,3,3',4,4'-hexa-O-benzylsucrose 
• 392699-44-4 6-O-acetyl-1,3,4-tri-O-benzyl-β-D-fructofuranosyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Visible-Light Responsive Sucrose-Containing Macrocyclic Host for Cations

Chiral photoresponsive host 1 was prepared by a high-yield Cs2CO3-templated macrocyclization. Trans-1 transforms into long-lived cis-1 (25 days) upon irradiation with green light, and the backward transformation is triggered by blue light. Both isomers pr

Synthesis of novel macrocyclic derivatives with a sucrose scaffold by the RCM approach

1′2,3,3′4,4′-Hexa-O-benzylsucrose was esterified at both terminal positions with an unsaturated acid derived from d-glucose. Cyclization of the resulting di-olefin under the RCM conditions afforded the corresponding 21-membered macrocyclic unsaturated di-

Microwave-assisted protocols applied to the synthesis of 1′,2,3,3′,4,4′-Hexa-O-benzylsucrose

The sucrose derivative 1′,2,3,3′,4,4′-hexa-O- benzylsucrose is a key intermediate for the chemoselective synthesis of various useful materials, such as macrocycles, crown ether analogs, and polymers. Several strategies for the synthesis of this compound were explored by applying microwave-assisted protocols, thus permitting significant reductions of time and energy compared to other routes. The outcomes of the different approaches were compared and the optimal one, in terms of yield and reproducibility, was found to be the initial protection at the positions 6 and 6′, with tert-butyldiphenylsilylchloride (TBDPSCl) in the presence of 4-(dimethylamino)pyridine (4-DMAP) and pyridine as a solvent, then perbenzylation of the remaining hydroxyl groups, followed by selective deprotection of the TBDPS groups to obtain the title compound.

Synthesis and complexation properties of unsymmetrical sucrose-based receptors

New unsymmetrical , sucrose-based diaza-crown ethers have been designed and prepared from monosilylated hexa-O-benzylsucrose derivatives. The enantioselective complexation of phenylethylammonium cations by these receptors was evaluated. It was demonstrated that the introduction of the amino group at the 6-position (glucose moiety) in sucrose increases the association constant for the S cation, but reduces the enantioselectivity. On the other hand, introduction of the amino group at the 6′-position (fructose moiety) in sucrose increases significantly the value of Ka and at the same time the high enantioselectivity is preserved. A new approach to sucrose-based macrocyclic receptors with an unsymmetrical arrangement of heteroatoms is presented. Their complexes with the (S)-α- phenylethylammonium cation are stronger than with the corresponding R cation. The enantioselectivity of the complexation depends on the position of the nitrogen atom(s) in the macrocyclic ring. Copyright

Synthesis of 6-O-hexadecyl-and 6-O-octylsucroses and their self-assembling properties under aqueous conditions

This paper reports the synthesis and self-assembling properties of 6-O-hexadecyl-and 6-O-octylsucroses. Mono-etherification of 2,3,4,1,3,4-hexa-O- benzylsucrose with the corresponding alkyl bromides predominantly took place at the glucose 6-position and t

Highly efficient and mild method for regioselective de-O-benzylation of saccharides by Co2(CO)8-Et3SiH-CO reagent system

[Chemical equation presented] A highly efficient and mild method for the de-O-benzylation of protected saccharides was developed by transforming terminal benzyl ethers Into silyl ethers using Co2(CO)8-Et 3SIH under 1 atm of CO. The method was successfully used for the de-O-benzylatlon of perbenzylated monosaccharides with various anomerlc protecting groups, as well as natural disaccharldes and trisaccharides such as sucrose, raffinose, and melezltose In good yields (>80%).

Synthesis of phosphorylated derivatives of sucrose: 6,6′-di- phosphonate, 6- and 6′-phosphonates, and 6,6′-di-phosphine

Reaction of 6,6′dideoxy-6,6′di-iodo-1′,2,3,3′,4, 4′-hexa-O-benzylsucrose with triethyl phosphite afforded the corresponding 6,6′-diphosphonate. Selective phosphonylation either at the C-6 or 6-6′ position was also possible providing the corresponding sucrose mono-phosphonates. Reaction of 6,6′-dichloro-hexa-O-benzylsucrose with diphenylphoshine anion afforded the 6,6′-diphosphinosucrose. Copyright Taylor & Francis Group, LLC.

Macrocyclic receptors containing sucrose skeleton

Crown ether analogues with incorporated sucrose unit were prepared by reaction of 1′,2,3,3′,4,4′-hexa-O-benzylsucrose with polyethylene ditosylates in up to 52% yield. Stability constants of their complexes with Li+, Na+, K+, NH 4+ were determined by the NMR titration method. The macrocycles were also tested as catalysts in the enantioselective Michael reaction, but with little success (ee up to only 22%). The macrocycle containing nitrogen in the ring was also prepared in good yield. All prepared macrocycles were easily converted into the free sucrose crowns (H2/Pd/C) without destroying the (very labile) glycosidic bond. The crystal structure of the selected receptor was determined.

Synthesis of Macrocyclic Derivatives Containing a Sucrose Unit

An efficient synthesis of 1′,2,3,3′4,4′-hexa-O- benzylsucrose (48% from sucrose) is presented. This diol was used for the preparation of crown ether-type analogs of various size macrocyclic rings with incorporated sucrose units.

Crown ether analogs from sucrose

A convenient synthesis of 1′,2,3,3′4,4′-hexa-O-benzylsucrose (4) from the free disaccharide is presented. Diol 4 and previously obtained 1′-O-benzyloxymethyl-2,3,3′,4,4′-penta-O-benzylsucrose (3) served as precursors for chiral crown ether analogs containing a sucrose backbone. Deprotection of macrocyclic compounds (removal of the benzyl blocks) was possible under hydrogenolysis conditions.