2296-40-4

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 709-50-2 methyl beta-D-glucopyranoside 
• 25561-30-2 trimethylsilyl 2,2,2-trifluoro-N-(trimethylsilyl)acetimidate 
• 67-56-1 methanol 
• 50-99-7 D-glucose 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 168138-24-7 Carbamic acid (2R,3R,4S,5S,6R)-3,5-dihydroxy-2-hydroxymethyl-6-((2R,3S,4S,5S,6S)-2,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 

Downstream Products

• 7726-97-8 1,4-anhydro-D-glucitol 
• 154-58-5 1,5-anhydro-D-glucitol 
• 129706-93-0 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 205598-17-0 1,6-deoxyglucitol 
• 187218-13-9 4-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-butyric acid (2R,3R,4S,5R,6R)-6-methoxy-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester 
• 142886-46-2 methyl 2,3,4-tri-O-acetyl-6-O-(4'-O-acetyl-p-coumaroyl)-β-D-glucopyranoside 
• 142886-43-9 methyl 6-O-(4'-O-acetyl-p-coumaroyl)-β-D-glucopyranoside 
• 135447-50-6 methyl 6-O-p-trans-coumaroyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Substrate specificity of tuliposide-converting enzyme, a unique non-ester-hydrolyzing carboxylesterase in tulip: Effects of the alcohol moiety of substrate on the enzyme activity

6-Tuliposides A (PosA) and B (PosB) are glucose esters accumulated in tulip (Tulipa gesneriana) as major defensive secondary metabolites. Pos-converting enzymes (TgTCEs), which we discovered previously from tulip, catalyze the conversion reactions of PosA

A new flavonoid diglycoside from Biophytum reinwardtii (Zucc.) Klotzsch. And evaluation of its antioxidant and anticancer activities

A new flavonoid diglycoside namely apigenin-4',5-O-β-D-diglucoside 1 has been isolated from the whole plant of Biophytum reinwardtii (Zucc.) Klotzsch. and its structure has been elucidated by a combination of spectroscopic (1H, 13C and 2D NMR spectroscopy), mass spectral data and chemical methods. The compound 1 has been evaluated for its antioxidant activities viz., DPPH free radical scavenging activity and modified ferric reducing/antioxidant power (FRAP) assay and anticancer activity viz., MTT assay. The compound 1 has been found to possess significant antioxidant and anticancer activities.

Catalytic Iron(III) Chloride Mediated Site-Selective Protection of Mono- and Disaccharides and One Trisaccharide

Regioselective differentiation of the hydroxy groups of mono- and oligosaccharide substrates is necessary to form building blocks that can be used for synthetic transformations. In this paper, we show that iron(III) chloride hexahydrate catalyses the tandem protection of mono- and disaccharides to give, in a one-pot procedure, selectively protected carbohydrate building blocks. This tandem protocol was successfully applied to a trisaccharide. The procedure is easy to carry out; for optimal results, each carbohydrate substrate required a fine tuning of the one-pot reaction conditions.

Characterization of ulvan extracts to assess the effect of different steps in the extraction procedure

An effective application development of the polysaccharide ulvan requires a comprehensive knowledge about the influence of the extraction process on composition of the extracts and in ulvan itself. In this context, the two main objectives of the present work are (1) the establishment of an efficient extraction process for ulvan and (2) development of an accurate characterization methodology to evaluate the extract composition and ulvan content. Three ulvan-rich extracts obtained by different schemes of extraction were studied. The methodology for the analysis was improved and a detailed analysis of extracted ulvan was provided. The polysaccharide is rich in ulvanobiuronic acid 3-sulfate type A [→4)-β-d-GlcAp-(1 → 4)-α-l-Rhap 3S-(1→], with minor amounts of ulvanobiuronic acid 3-sulfate type B [→4)-α-l-IdoAp-(1 → 4)-α-l-Rhap 3S-(1→]. The extract with the higher degree of purification is a high molecular weight polysaccharide (790 kDa) composed of rhamnose (22.4%), glucuronic acid (22.5%), xylose (3.7%), iduronic acid (3.1%) and glucose (1.0%). It is highly sulfated (32.2%) and contains 1.3% of proteins and 10.3% of inorganic material. Applying simple extraction scheme it was possible to obtain an extract from green algae with high content of ulvan without affecting the overall chemical structure of the polysaccharide.

Synthesis of tulipalin B and 1-O-methyl-6-tuliposide B

Toward the total synthesis of 6-tuliposide B, facile synthesis of tulipalin B and 1-O-methyl-6-tuliposide B (Methyl 6-0-((S)-3′,4′-dihydroxy-2′-methylenebutanoyl)-β-D-glucopyranoside) has been achieved.

Large-scale synthesis of D-mannose 6-phosphate and other hexose 6-phosphates

The syntheses of D-mannose 6-phosaphate (4), several D-mannopyranoside 6-phosphates, and methyl α-D-glucopyranoside 6-phosphate are described.Phophorylation of methyl 2,3,4-tri-O-(trimethylsilyl)-α-D-mannopyranoside (2) with phosphorus oxychloride followe

A convenient method for the cleavage of the D-mannosyl-L-gulose disaccharide from bleomycin-A2.

In order to elucidate the biological role of the sugar residue of the antitumor drug bleomycin, this was deglycosylated by beta-elimination under mild alkaline conditions, and by solvolysis with hydrogen fluoride. The latter procedure proved to be better because it led to the complete deglycosylation without modification of the peptide, thus allowing further biological investigations of this component.

An Efficient Synthesis of Anhydroalditols and Allyl C-Glycosides

Efforts to expedite production of anhydroalditols have led to a new, efficient synthesis of these compounds from alkyl glycosides.Silylation of the glycoside followed by reductive cleavage in the presence of triethylsilane and trimethylsilyl trifluoromethanesulfonate were carried out in the same reaction flask.Subsequent aqueous workup gave excellent yields of anhydroalditol(s).In some cases ring contraction was observed, but the use of bulkier silyl protecting groups gave greater yields of the expected product.This method was also shown to be an efficient means to prepare allyl C-glycosides, without any independent protecting or activating step, by simply replacing triethylsilane with allyltrimethylsilane in the synthetic scheme.