65827-58-9

Usage

Chemical Properties

Oil

InChI:InChI=1/C21H26O10/c1-12(22)26-11-17-18(28-13(2)23)19(27-10-16-8-6-5-7-9-16)20(29-14(3)24)21(31-17)30-15(4)25/h5-9,17-21H,10-11H2,1-4H3/t17?,18-,19+,20-,21+/m1/s1

Upstream product

• 3458-28-4 D-Mannose 
• 65877-63-6 3-O-benzyl-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 97590-76-6 benzyl-O-β-D-glucopyranoside 
• 10230-17-8 O³-benzyl-D-glucose 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 93714-01-3 methyl 3-O-benzyl-α-D-mannopyranoside 
• 1309382-33-9 methyl-6-(tert-butyldimethylsilyloxy)-3-O-benzyl-α-D-mannopyranoside 
• 74247-81-7 6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 3162-96-7 methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 

Downstream Products

• 39708-09-3 methyl-(O³-benzyl-O²,O⁴,O⁶-trimethyl-ξ-D-glucopyranoside) 
• 124813-93-0 benzyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 87791-22-8 1-O-Acetyl-3-O-benzyl-2,4,6-tri-O-methyl-β-D-glucopyranose 
• 87791-21-7 1-O-Acetyl-3-O-benzyl-2,4,6-tri-O-methyl-α-D-glucopyranose 
• 80064-96-6 N⁴-acetyl-1-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)cytosine 
• 124813-99-6 methyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)-α-D-mannopyranoside 
• 124814-09-1 C₈₀H₈₆O₁₉ 
• 146530-62-3 ethyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside 
• 22331-16-4 phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside 
• 22331-15-3 phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranoside 
• 103082-79-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-α-D-glucopyranose 
• 158198-55-1 phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside 
• 189144-47-6 2,4,6-tri-O-acetyl-3-O-benzyl-alpha-D-glucopyranosyl chloride 
• 303127-79-9 4-Methoxyphenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups

The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow.

Synthesis of helicobacter-pylorus O2 serotype O antigen oligosaccharide compound

The invention discloses discloses synthesis of a helicobacter-pylorus O2 serotype O antigen oligosaccharide compound, and belongs to the field of organic synthesis. According to the synthesis, helicobacter-pylorus O2 serotype O-antigen disaccharide to tet

Intercepted dehomologation of aldoses by N-heterocyclic carbene catalysis-a novel transformation in carbohydrate chemistry

The development of an N-heterocyclic carbene (NHC) catalysed intercepted dehomologation of aldoses is reported. The unique selectivity of NHCs for aldehydes is exploited in the complex context of reducing sugars. Examples of strong substrate governance for either intercepted dehomologation or a subsequent redox-lactonisation were identified and mechanistically understood. More importantly, it was shown that catalyst design allowed the tuning of the selectivity of the reaction with structurally unbiased starting materials towards either of the two scenarios.

Multi-gram scale synthesis of a bleomycin (BLM) carbohydrate moiety: exploring the antitumor beneficial effect of BLM disaccharide attached to 10-hydroxycamptothecine (10-HCPT)

The “tumor-seeking” role of bleomycin (BLM) disaccharide has been demonstrated to serve as a promising tool for cancer diagnosis and a potential ligand for targeted therapy. However, these practical applications are often hampered by the lack of BLM disaccharide. Herein, an efficient multi-gram synthesis of peracetylated BLM disaccharide 20 is achieved by a TMSOTF-mediated glycosidation coupling manner in 43.6% overall yield in terms of benzyl galactoside. The critical innovation of the synthetic strategy is that inexpensive benzyl galactoside was first adopted to prepare an l-gulose subunit 3 as a glycosyl acceptor, with a much shorter route in 73.0% yield, and a 3-O-carbamoyl-mannose donor 4 was achieved in 47.2% yield by lowering the amount of dibutyltin oxide, and merging aminolysis and selective deacetylation into a one-pot reaction. Next, the incorporation of BLM disaccharide into 10-hydroxycamptothecin (10-HCPT), a non-specific model compound, to form conjugate 1 could significantly improve the antitumor activity and display obvious selectivity toward cancerous and normal cells in comparison with 10-HCPT. Moreover, BLM disaccharide itself was non-cytotoxic, clearly indicating the importance and potential of BLM disaccharide in solving the targeted antitumor therapy of cytotoxic drugs.

Preparation method of clostridium bolteae surface capsular polysaccharide structure derivative

The invention discloses a preparation method of a clostridium bolteae surface capsular polysaccharide structure derivative and belongs to the field of sugar chemistry. The preparation method comprisesthe following steps: taking glucose as a glycosyl donor to obtain a target beta-glycosidic bond; then successfully synthesizing a disaccharide building block through an oxidization-reduction glucoseC-2 site method; then synthesizing a target oligosaccharide structure which takes the disaccharide building block as a repeating unit, such as the gram-positive bacterium surface capsular polysaccharide structure derivative [arrow3]-alpha-D-Manp-(1arrow4)-beta-D-Rhap-(1arrow]5-Linker. A reducing end of decaose is connected with a connecting arm and is used for connecting protein to form a glycoconjugate for carrying out immunology researches. The method provided by the invention has the advantages of simplicity, time saving, labor saving and low cost; the obtained clostridium bolteae surface capsular polysaccharide structure derivative is possibly used for developing and preparing medicine related to autism.

Total synthesis of viscumneoside III of Viscum coloratum

The first total synthesis of viscumneoside III, a promising anti-angina pectoris dihydroflavone O-glycoside isolated from Viscum coloratum was described here. Trichloroaceti-midate was employed as the apiofuranosyl donor to construct the key building block of homoeriodictyol-7-O-β-D-apiosyl-(1 → 2)-β-D-glycoside (1). The longest linear sequence (from 2 to 1) in the synthetic route required thirteen steps and afforded the final product 1 with an overall yield of 6.3%.

Preparation methods of 2-hydroxygulose receptor derivative, bleomycin disaccharide and precursor of bleomycin disaccharide

The invention discloses a preparation method of a 2-hydroxygulose receptor derivative. The method comprises the following steps: carrying out a series of reactions of ylidene protection on benzyl-beta-galactoside, 3-position configuration inversion, deacetylation, and selective acetylation. Meanwhile, the invention also discloses a method for preparing bleomycin disaccharide and a precursor of bleomycin disaccharide by using the 2-hydroxygulose receptor derivative prepared by the method as a receptor. According to the invention, through the adoption of the preparation method of the 2-hydroxygulose receptor derivative, the problems that sources of natural L-gulose are rare, cost is too high, and industrialization is not facilitated and the like are solved; meanwhile, the problems that the bleomycin disaccharide and the precursor of the bleomycin disaccharide are low in yield, reaction operability and repeatability are poor, industrialization is not facilitated and the like are solved. The preparation methods have the advantages that raw materials are cheap and easily available, the yield is high, the operability is high, conditions can be easily controlled, industrial amplificationcan be realized, efficiency is high, cost is low, and the like.

Automated glycan assembly of a s. pneumoniae serotype 3 cps antigen

Vaccines against S. pneumoniae, one of the most prevalent bacterial infections causing severe disease, rely on isolated capsular polysaccharide (CPS) that are conjugated to proteins. Such isolates contain a heterogeneous oligosaccharide mixture of differe

SUGAR-LINKER-DRUG CONJUGATES

The present disclosure relates to sugar-linker-drug conjugates, of the formula [A-B-]n-L-D, wherein A is a saccharide; B is a spacer, n is an integer selected from 1 to 3; L is a linker group and D is a drug having a chemically reactive functional group selected from the group consisting of a primary or secondary amine, hydroxyl, sulfhydryl, carboxyl, aldehyde and ketone. Pharmaceutical compositions comprising the conjugates and methods of using thern are also provided.

SACCHARIDE CONJUGATES

This invention relates to compounds comprising a saccharide conjugated to an imaging agent or a reporter group, compositions comprising them and methods of using them. Specifically BLM-disaccharide and BLM-monosaccharide conjugates containing different linker groups and an imaging agent or a reporter group are provided for the targeting and imaging of tumors.