80779-87-9

Usage

Uses

Used in Pharmaceutical Industry:
2-O-Benzyl-1,3,4,6-tetra-O-acetyl-a-D-mannopyranose is used as a key intermediate in the synthesis of complex carbohydrates and glycoconjugates, which are important for the development of new drugs and therapeutic agents. These glycoconjugates can be used to target specific cells or tissues, improving the efficacy and reducing the side effects of drugs.
Used in Chemical Industry:
2-O-Benzyl-1,3,4,6-tetra-O-acetyl-a-D-mannopyranose is used as a building block for the preparation of various complex carbohydrate structures, which can be used in the synthesis of natural products, polymers, and other organic compounds. 2-O-Benzyl-1,3,4,6-tetra-O-acetyl-a-D-mannopyranose can also be used in the preparation of the corresponding bromide, which is an important reagent for the synthesis of -mannosides, a class of compounds with potential applications in various fields.
Used in Research and Development:
2-O-Benzyl-1,3,4,6-tetra-O-acetyl-a-D-mannopyranose is used as a research tool for studying the structure, properties, and functions of carbohydrates and glycoconjugates. It can be used to investigate the role of carbohydrates in biological processes, such as cell recognition, signaling, and adhesion, as well as their potential applications in drug discovery and development.

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

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 108-24-7 acetic anhydride 
• 15038-71-8 methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 
• 80738-49-4 methyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranoside 
• 52579-97-2 1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose 
• 100-39-0 benzyl bromide 
• 55287-62-2 O²-benzyl-O³,O⁴-isopropyliden-1,6-anhydro-β-D-galactopyranose 

Downstream Products

• 53872-78-9 3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-galactopyranosyl bromide 
• 79705-36-5 Benzyl-2,3-O-isopropyliden-4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid 
• 79705-41-2 Benzyl-4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid 
• 79705-33-2 (2,2,2-Trichlorethyl)-2,3-O-isopropyliden-4-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid 
• 79705-42-3 Benzyl-4-0-(2-O-benzyl-α-D-galactopyranosyl)-α-L-rhamnopyranosid 
• 55287-66-6 Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-2-acetoxymethyl-5-benzyloxy-6-chloro-tetrahydro-pyran-3-yl ester 
• 791611-43-3 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-tridecyloxy)-tetrahydro-pyran-4-yl ester 
• 791611-46-6 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-hexadecanoylamino-octadecyloxy)-tetrahydro-pyran-4-yl ester 
• 791611-42-2 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-nonyloxy)-tetrahydro-pyran-4-yl ester 
• 791611-41-1 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-tetracosanoylamino-hexyloxy)-tetrahydro-pyran-4-yl ester 
• 791611-45-5 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-octanoylamino-octadecyloxy)-tetrahydro-pyran-4-yl ester 
• 791611-44-4 Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2S,3S,4R)-3,4-diacetoxy-2-acetylamino-octadecyloxy)-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

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.

Modified bleomycin disaccharides exhibiting improved tumor cell targeting

The bleomycins (BLMs) are a family of antitumor antibiotics used clinically for anticancer chemotherapy. Their antitumor selectivity derives at least in part from their ability to target tumor cells, a property that resides in the carbohydrate moiety of the antitumor agent. In earlier studies, we have demonstrated that the tumor cell selectivity resides in the mannose carbamoyl moiety of the BLM saccharide and that both the BLM disaccharide and monosaccharide containing the carbamoyl moiety were capable of the delivery/uptake of a conjugated cyanine dye into cultured cancer cell lines. Presently, the nature of the participation of the carbamoyl moiety has been explored further to provide compounds of utility for defining the nature of the mechanism of tumor cell recognition and uptake by BLM saccharides and in the hope that more efficient compounds could be identified. A library of seven disaccharide-Cy5 dye conjugates was prepared that are structural analogues of the BLM disaccharide. These differed from the natural BLM disaccharide in the position, orientation, and substitution of the carbamoyl group. Studies of these compounds in four matched sets of tumor and normal cell lines revealed a few that were both tumor cell selective and internalized 2-4-fold more efficiently than the natural BLM disaccharide.

Effects of lipid chain lengths in α-galactosylceramides on cytokine release by natural killer T cells

Glycolipid presentation by CD1 proteins has emerged as an important aspect of antigen recognition, and presentation of α-glycosylceramides by CD1d to natural killer T cells has become a central focus in understanding how glycolipid presentation can influence immune responses. An α-galactosylceramide containing relatively long lipid chains has been the subject of intense study because, when presented by CD1d to natural killer T cells, it stimulates the release of both proinflammatory and immunomodulatory cytokines. Using an efficient synthesis of α-galactosylceramides, we have prepared a series of glycolipids in which the lipid chain lengths have been incrementally varied. The responses of natural killer T cells to these glycolipids have been determined, and we have found that truncation of the phytosphingosine lipid chain increases the relative amounts of immunomodulatory cytokines released. In similar fashion, the length of the acyl chain in α-galactosylceramides influences cytokine release profiles. Copyright

RECONSTRUCTION OF GLYCAN CHAINS OF GLYCOPROTEIN BRANCHING MANNOPENTAOSIDE AND MANNOHEXAOSIDE

Synthetic routes to the branching mannopentaoside 4 and mannohexaoside 5 are described employing properly protected mannobioside 13 as a key intermediate.