85572-59-4

Upstream product

• 2280-44-6 D-Glucose 
• 76-83-5 trityl chloride 
• 98-88-4 benzoyl chloride 
• 50-99-7 D-glucose 
• 54325-28-9 6-O-trityl-D-glucopyranose 
• 54325-28-9 (2R,3R,4S,5S,6R)-6-Trityloxymethyl-tetrahydro-pyran-2,3,4,5-tetraol 

Downstream Products

• 1611474-34-0 2,3,4-tri-o-benzoyl-6-O-9-fluorenylmethyloxycarboxyl-α-D-glucopyranosyl bromide 
• 104707-01-9 1,2,3,4-tetra-O-benzoyl-β-D-glucopyranose 
• 1611474-38-4 C₄₉H₃₈O₁₂ 
• 1611474-40-8 C₅₆H₅₆O₁₃Si 
• 1611474-42-0 C₄₈H₄₄O₁₁ 
• 1611474-43-1 cyclohexyl 2,3,4-tri-O-benzoyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Glycosylation of a newly functionalized orthoester derivative

Tandem glycosylation of the 6-O-Fmoc-substituted benzyl orthoester derivative 2a was carried out in moderate yields by electrogenerated acid (EGA). The Fmoc group was effectively removed under mild basic conditions, and the product was submitted to the subsequent glycosylation.

First total synthesis of two new diglycosides, neohancosides A and B, from Cynanchum hancockianum

Neohancosides A (1) and B (2) are monoterpene diglycosides isolated from Cynanchum hancockianum, which is a Chinese folk medicine having antitumor activity. First total synthesis of 1 and 2, (3R)-linaloyl and (3R)-8-hydroxylinaloyl 3-O-β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranosides were achieved stereoselectively using fluoride 12b as a glycosyl donor. The asymmetry of C-3 in 1 and 2 was introduced efficiently by separating diasteremers of (3R), (3S)-linaloyl and (3R), (3S)-8-benzoyloxylinaloyl 3-O-2,3,4-tri-O-benzoyl-β-D-glucopyranoside, 19 and 21 and 20 and 22, respectively. Absolute configurations of 1 and 2 were determined by enzymatic degradation of synthetic intermediates 33 and 34.

Synthesis of a new phenol glycoside, neohancoside C from Cynanchum hancockianum

Neohancoside C (1) is a new phenol glycoside isolated from Cynanchum hancockianum, which is a Chinese folk medicine having antitumor activity. The synthesis of 1, 2-acetylphenyl β-D-xylopyranosyl-(1→6)-β-D-gluco- pyranoside, was achieved by phase-transfer

First total synthesis of new diglycosides, neohancoside A, and B from Cynanchum hancockianum

First total synthesis of monoterpene diglycosides, neohancosides A (1) and B (2) from Cynanchum hancockianum were achieved stereoselectively using fluoride as a glycosyl donor. The absolute configurations of 1 and 2 were determined by enzymatic degradation of synthetic intermediates.

TiCl4-CATALYZED CONVERSION OF 1,2,3,4-TETRA-O-ACETYL-6-O-TRITYL-β-D-GLUCOPYRANOSE INTO TRIACETYLLEVOGLUCOSAN - THE MECHANISM OF THE REACTION

In chloroform solutions containing some alcohol, 1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose is transformed, on the effect of TiCl4, into triacetyllevoglucosan, which can be isolated in the pure state in 70 percent yield.The method has also been found suitable for the preparation of the tribenzoyl derivative.The conversion takes place in two steps, a rapid detritylation followed by a slower cyclization process.During detritylation, a compound of the alkoxytitanium trichloride type is formed.In the cyclization step this loses AcOTiCl3, which formes a coordination complex with triacetyllevoglucosan in an equilibrium reaction, or an ionic complex with trityl chloride.