94591-55-6

Upstream product

• 60-12-8 2-phenylethanol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 14861-16-6 2-phenylethyl-β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 100-66-3 methoxybenzene 
• 604-69-3 β-D-glucose pentaacetate 
• 157242-09-6 2-phenylethyl α/β-glucoside 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 572-09-8 acetobromogalactose 
• 604-68-2 α-D-glucopyranose peracetylate 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 83-87-4 D-glucose pentaacetate 
• 1464-44-4 phenyl-β-D-glucopyranoside 

Downstream Products

• 911817-13-5 2-phenylethyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 1436383-91-3 2-phenylethyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→3)-2-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 1436383-92-4 2-phenylethyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→3)-2-O-acetyl-β-D-glucopyranoside 
• 14861-16-6 2-phenylethyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis and conformational analysis of plant hormone (auxin) related compound 2-(indol-3-yl) ethyl β-D-galactopyranoside and its 2,3,4,6-tetra-O-acetyl derivative

The synthesis, structure analysis by X-ray diffraction and NMR spectroscopy (including 1H{1H}NOEs) of 2-(indol-3-yl)ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (4) are described. The per-O-acetylated derivative of 2-(indol-3-yl)ethyl β-D-galactopyranoside (4*) was prepared along with the isomeric α-D-galactopyranose 1,2-orthoacetates (3 exo- and endo-stereomers) by condensation of 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (1) with the aglycone alcohol (2). The analogous condensation of 1 and 2-phenylethanol yielded a mixture of 2-phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (6) and isomeric α-D-galactopyranose 1,2-orthoacetates (5). Compound 4 crystallized in the monoclinic system, space group C2, a = 22.385(2), b = 7.865(2), c = 28.761(3) A, β = 102.1(1)°, Z = 8, with two symmetrically independent molecules in the asymmetric unit. In both molecules β-D-galactopyranose rings are in the 4C1 chair conformation. The conformational analysis of 4 and the analogous unprotected conjugate (4*), based on molecular mechanics calculations and molecular dynamics simulations, is presented. The conformational stability about the bond of conjugation and relative orientation of the indole ring towards the β-D-galactopyranose moiety are discussed.

Synthesis, biological activity of salidroside and its analogues

Salidroside is a phenylpropanoid glycoside isolated from Rhodiola rosea L., a traditional Chinese medicinal plant, and has displayed a broad spectrum of pharmacological properties. In this paper, about 18 novel salidroside analogues were prepared through Koenigs-Knorr method, the effects of these compounds over PC12 was assessed with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. The novel compounds differ in the substituents attached to the benzene ring or in the glycosyl donor. According to the data, compounds (3,5-dimethoxyphenyl)methyl β-D-glucopyranoside and (3,5-dimethoxyphenyl) methyl β-D-galactopyranoside with methoxy group at 3 and 5-positions of the benzene ring were the most viability at concentration of 300 μmol/l and 60 μmol/l, respectively.

Synthesis, characterization and application study of two glycosides as flavour precursors

Two glycosides of benzyl alcohol and phenethyl alcohol as flavour precursors have been synthesized and their structures were characterized by IR, 1H NMR spectra and ESI-MS. Their pyolysis products are investigated by the on-line pyrolysis gas chromatography-mass spectroscopy. Their transfer efficiency from tobacco to cigarette smoke was determined for evaluation of its possibility of application.

Facile preparation of α-glycosyl iodides by in situ generated aluminum iodide: Straightforward synthesis of thio-, seleno-, and o-glycosides from unprotected reducing sugars

A facile and practical protocol was developed for the synthesis of glycosyl iodides using AlI3 generated in situ from cheap aluminum metal and molecular iodine. Furthermore, in combination with iodine-catalyzed per-O-acetylation, sequential synthesis of per-acetylated glycosyl iodides, per-acetylated thioglycosides, selenoglycoside, and O-glycosides from unprotected reducing sugars was also achieved with complete diastereocontrol in a one-pot version. Supplemental material is available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

A convenient stereoselective synthesis of β-D-glucopyranosides

The Koenigs-Knorr method plays a prominent role in the stereoselective synthesis of alkyl D-glucopyranosides via glycosidic linkage. Such an approach requires costly and toxic promoter salts of silver or mercury, which have additional separation problems. In a novel method a less toxic promoter salt like LiCO3 is used for glycosidation of several fatty alcohols including an aromatic alcohol. LiCO3 can be easily separated from the reaction mass and gives good yield.

GC-MS characterization of acetylated β-D-glucopyranosides: Transglucosylation of volatile alcohols using almond β-glucosidase

β-D-Glucopyranosides of pentan-1-ol, (±)-pentan-2-ol, hexan-1-ol, octan-1-ol, benzyl alcohol, 2-phenylethanol, (±)-2-phenyl- propan-1-ol, 3-phenyl-propan-1-ol, geraniol and nerol were synthesized by transglucosylation of the respective alcohols with cellobiose using almond β-glucosidase. The reaction was carried out in acetonitrile with acetate buffer (vol. ratio 9:1), with the yields 14.4-45.0 %. Transglucosylation was not enantioselective. The products were characterized by GC-MS analysis of prepared tetraacetyl glucosides. Fragment ion characteristics of the aglucone moiety are present in all mass spectra, along with the fragments obtained from acetylated glucose. Acetylated glucosides are separable on HP-101 column (even diastereomeric tetraacetyl β-glucosides of enantiomeric alcohols).

Isolation of a Glucosidic β-Damascenone Precursor from Rose Petals

The 9-O-β-D-glucopyranoside of 3-hydroxy-7,8-didehydro-β-ionol (1) has been isolated from a glycosidic XAD-2 extract obtained from rose petals. In addition to the β-damascenone-generating compound 1, the following glycoconjugates have been isolated and characterized as peracetates: 3-hydroxy-7,8-dihydro-β-ionol 9-O-β-D-glucopyranoside (2), 3-hydroxy-7,8-dihydro-β-ionol 3-O-β-D-glucopyranoside (3), 2-phenylethyl-O-β-D-glucopyranoside (4), 2-phenylethyl-O-β-D-galactopyranoside (5), benzyl-O-β-D-glucopyranoside (6), (2E)-2,6-dimethyl-6-hydroxyocta-2,7-dienyl-O-β-D-glucopyranoside (7), (2Z)-2,6-dimethyl-6-hydroxyocta-2,7-dienyl-O-β-D-glucopyranoside (8), and (2E,6E)-2,6-dimethyl-1-hydroxyocta-2,6-dien-8-yl-O-β-D-glucopyranoside (9).

Sensitive and Selective Screening for 6′-O-Malonylated Glucoconjugates in Plants

Using synthesized reference compounds a screening for benzyl, 2-phenylethyl, geranyl, citronellyl, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone 6′-O-malonyl β-D-glucopyranosides in various plant tissues was performed by high-performance liquid chromatography - electrospray ionization - tandem mass spectrometry (HPLC-ESI-MS/MS). The results obtained with fruits (guava; raspberry; strawberry), leaves (green tea; vine), and mountain papaya (Carica pubescens) peel indicate that malonylation of glycoconjugates is a common pathway in plant secondary metabolism.

Synthesis of 2-Phenylethyl α-Glucoside

2-Phenylethyl α-glucoside was synthesized from 2-phenylethanol and α-D-glucose in the presence of p-toluenesulfonic acid monohydrate at 75 deg C and was isolated by continuous extraction, during which hexane was used to remove the excess 2-phenylethanol and then ethyl acetate was used to isolate the product.The spectral data including IR, 1H NMR, 13C NMR, and MS of this compound are presented. Keywords: 2-Phenylethanol; 2-phenylethyl α-glucoside; α-D-glucose; p-toluenesulfonic acid