686299-00-3

Upstream product

• 75-08-1 ethanethiol 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 125354-48-5 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside 
• 3458-28-4 D-Mannose 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 492-61-5 β-D-glucose 
• 83-87-4 D-glucose pentaacetate 
• 1941-52-2 D-glucose diethyl mercaptal 
• 50-99-7 D-glucose 
• 4137-33-1 ethyl 1-thio-α-D-glucofuranoside 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 
• 1290085-45-8 2,3:4,5-di-O-isopropylidene-β-D-glucoseptanose 
• 1379587-23-1 ethyl 1-thio-2,3:4,5-di-O-isopropylidene-α-D-glucoseptanoside 

Downstream Products

• 13121-61-4 tetra-O-acetyl-1,5-anhydro-D-mannitol 
• 151725-48-3 ethyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside 
• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 
• 55722-49-1 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 116872-14-1 Ethyl 2,3,4,6-tetra-O-p-chlorobenzyl-1-thio-β-D-galactopyranoside 
• 203514-18-5 ethyl 4-O-acetyl-2,6-di-O-benzoyl-1-thio-β-D-galactopyranoside 
• 322761-81-9 ethyl 3-O-[(1S)-1-(cyclohexylmethyl)-2-oxo-2-(phenylmethoxy)ethyl]-1-thio-β-D-galactopyranoside 2,4,6-tribenzoate 
• 90358-01-3 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl α-D-galactopyranoside 

Relevant academic research and scientific papers

A versatile approach to the synthesis of glycans containing mannuronic acid residues

Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3-O-picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linkedviaβ-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3-O-benzoyl group is also reported.

Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof

The invention discloses a beta-D-glucose short-chain fatty acid ester compound as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The compound is a compound shown as a formula I, or a stereoisomer, a pharmaceutically acceptable salt, a solvate or a prodrug of the compound shown as the formula I. The formula is as shown in the description, wherein R is a methyl group, an ethyl group, a propyl group, a propylene group, an isopropylidene group, a butyl group, a butylidene group, an isobutylidene group, an amyl group, a pentylidene group or an isoamylidene group. The compound has potential prevention and treatment effects on diabetes, hyperlipidemia, atherosclerosis, Alzheimer's disease, cardiovascular and cerebrovascular diseases,inflammation, tumors and depression.

GLUCOSE TRIPTOLIDE CONJUGATES AND USES THEREOF

A major hurdle in the treatment of cancer is chemoresistance induced under hypoxia that is characteristic of tumor microenvironment. Triptolide, a potent inhibitor of eukaryotic transcription, possesses potent antitumor activity. However, its clinical potential has been limited by toxicity and water solubility. To address those limitations of triptolide, the present disclosure designed and synthesized glucose-triptolide conjugates (glutriptolides) and demonstrated their antitumor activity in vitro and in vivo. The glutriptolides disclosed herein possess improved stability in human serum, greater selectivity towards cancer over normal cells and increased potency against cancer cells. Importantly, the glutriptolides are more potent against cancer cells under hypoxic conditions in contrast to existing cytotoxic drugs. These glutriptolides also exhibit sustained antitumor activity, prolonging survival in a prostate cancer metastasis animal model. Together, these findings suggest a new strategy to overcome chemoresistance through conjugation of cytotoxic agents to glucose.

A versatile approach to the synthesis of mannosamine glycosides

O-Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O-picoloyl group at the C-3 position of a mannosamine donor can provide high or complete stereocontrol. The method was also utilized for the synthesis of a biologically relevant trisaccharide related to the capsular polysaccharide of Streptococcus pneumoniae serotype 4. Also reported herein is a method to achieve complete α-manno stereoselectivity with mannosamine donors equipped with 3-O-benzoyl group. This journal is

Enzyme-Catalyzed Regioselective Acetylation of Functionalized Glycosides

Novozym 435 (N435) is an immobilized lipase (Candida antarctica lipase B) capable of catalyzing transesterfications in organic media. This paper describes how this enzyme can be used for regioselective acetylation of unprotected carbohydrates providing protected monosaccharide building blocks in only one step. Unprotected thiogylcosides with both gluco, xylo, and manno stereochemistry were tolerated by the enzyme and afforded the acetylated products in high yields. The regioselective acetylation was easily scaled up to a 5.0 gram scale and in most cases, no purification was needed. Several other glycosides, including 2-azido-2-deoxy glucosides, galactosides, and gluconolactones, were also acetylated and the scope and limitations using N435 has been uncovered.

One-Pot Relay Glycosylation

A novel one-pot relay glycosylation has been established. The protocol is characterized by the construction of two glycosidic bonds with only one equivalent of triflic anhydride. This method capitalizes on the in situ generated cyclic-thiosulfonium ion as the relay activator, which directly activates the newly formed thioglycoside in one pot. A wide range of substrates are well-accommodated to furnish both linear and branched oligosaccharides. The synthetic utility and advantage of this method have been demonstrated by rapid access to naturally occurring phenylethanoid glycoside kankanoside F and resin glycoside merremoside D.

Chemical glucosylation of pyridoxine

The chemical synthesis of pyridoxine-5′-β-D-glucoside (5′-β-PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α4,3-O-isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′-β-PNG.

Ring Expansion Leads to a More Potent Analogue of Ipomoeassin F

Two new ring-size-varying analogues (2 and 3) of ipomoeassin F were synthesized and evaluated. Improved cytotoxicity (IC50: from 1.8 nM) and in vitro protein translocation inhibition (IC50: 35 nM) derived from ring expansion imply that the binding pocket of Sec61α (isoform 1) can accommodate further structural modifications, likely in the fatty acid portion. Streamlined preparation of the key diol intermediate 5 enabled gram-scale production, allowing us to establish that ipomoeassin F is biologically active in vivo (MTD: μ3 mg/kg).

Visible Light Enables Aerobic Iodine Catalyzed Glycosylation

A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.

Synthesis of 12- O-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle

Fifteen glycosyl-oxystearates were synthesized by Crich's 4,6-benzylidene and K?ening-Knorr strategies. Assessment of structure-activity relationships using macrophage-inducible C-type lectin (Mincle) receptor cells expressing nuclear factor of activated