187022-49-7

Usage

Uses

Used in Biochemistry Research:
Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside is utilized as a synthetic intermediate for the modification of carbohydrates, facilitating the study of glycosylation and its implications in various biological processes.
Used in Organic Chemistry Research:
In the field of organic chemistry, Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside is employed as a synthetic intermediate, enabling the exploration of complex carbohydrate structures and their interactions within organic systems.
Used in Pharmaceutical Research and Development:
Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside is leveraged in pharmaceutical research as a potential precursor for the development of novel drugs, given its unique structural features that may offer new avenues for therapeutic intervention.
Used in Drug Design and Synthesis:
In the pharmaceutical industry, Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-glucopyranoside is used as a key building block in the design and synthesis of new drug candidates, capitalizing on its capacity to be modified and incorporated into diverse molecular frameworks for targeted therapeutic effects.

InChI:InChI=1/C21H24Cl3NO9S/c1-11(26)30-9-15-17(32-12(2)27)18(33-13(3)28)16(25-20(29)31-10-21(22,23)24)19(34-15)35-14-7-5-4-6-8-14/h4-8,15-19H,9-10H2,1-3H3,(H,25,29)/t15-,16-,17+,18+,19-/m0/s1

Upstream product

• 108-98-5 thiophenol 
• 187022-27-1 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 
• 122210-01-9 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 108-24-7 acetic anhydride 
• 17341-93-4 2,2,2-Trichloroethyl chloroformate 
• 136945-14-7 O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate 
• 675876-42-3 (2S,3R,4R,5R,6R)-3-Azido-5-benzyloxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-ol 
• 676227-82-0 ((2S,4aR,6S,7R,8R,8aS)-7-Azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-tert-butyl-dimethyl-silane 
• 122210-05-3 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose 
• 172490-46-9 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 
• 819798-40-8 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 
• 148416-94-8 phenyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside 
• 819798-39-5 phenyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside 

Downstream Products

• 188583-12-2 N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester 
• 188583-24-6 phenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 
• 263010-53-3 N-(tert-butoxycarbonyl)-glycyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serine benzyl ester 
• 944060-21-3 C₃₇H₄₃Cl₃N₂O₁₅ 
• 944060-23-5 C₄₉H₅₆NO₁₈P 
• 512174-10-6 phenyl O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 
• 744193-99-5 phenyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 
• 263010-54-4 N-(tert-butoxycarbonyl)-glycyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranosyl]-L-serine benzyl ester 
• 188583-25-7 phenyl 2-[(2,2,2-trichloroethoxy)carbonyl]amino-4,6-O-p-methoxybenzylidene-2-deoxy-1-thio-β-D-glucopyranoside 
• 188583-27-9 phenyl 2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 
• 188583-28-0 phenyl 6-O-benzyloxymethyl-2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 
• 1054657-29-2 (2S,3S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxy)-2-tetradecanoylamino-butyric acid benzyl ester 
• 188583-26-8 phenyl 2-deoxy-4,6-O-p-methoxybenzylidene-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of LewisX-O-Core-1 threonine: A building block for O-linked LewisX glycopeptides

LewisX (LeX) is a branched trisaccharide Galβ1→4(Fucα1→3)GlcNAc that is expressed on many cell surface glycoproteins and plays critical roles in innate and adaptive immune responses. However, efficient synthesis of glycopeptides bearing LeX remains a major limitation for structure-function studies of the LeX determinant. Here we report a total synthesis of a LeX pentasaccharide 1 using a regioselective 1-benzenesulfinyl piperidine/triflic anhydride promoted [3 + 2] glycosylation. The presence of an Fmoc-threonine amino acid facilitates incorporation of the pentasaccharide in solid phase peptide synthesis, providing a route to diverse O-linked LeX glycopeptides. The described approach is broadly applicable to the synthesis of a variety of complex glycopeptides containing O-linked LeX or sialyl LewisX (sLeX).

A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.

Protecting group-free glycoligation by the desulfurative rearrangement of allylic disulfides as a means of assembly of oligosaccharide mimetics

2-(2-Pyridyldithio-3-butenyl) glycosides react with carbohydrate-based thiols in a two-step process involving sulfenyl transfer followed by desulfurative 2,3-allylic rearrangement, promoted by either triphenylphosphine or silver nitrate, to give novel saccharide mimetics. In an alternative embodiment of the same chemistry anomeric thiols are coupled with carbohydrates derivatized in the form of 2-(2-pyridyldithio-3-butenyl) ethers. This new method of glycoligation does not require protection of hydroxyl groups and is compatible with the presence of acetamides, azides, trichloroethoxycarbamates, and thioglycosides. Variations on the general theme enable the preparation of mimetics of reducing and nonreducing oligosaccharides as well as of nonglycosidically linked systems.

MOENOMYCIN ANALOGS, METHODS OF SYNTHESIS, AND USES THEREOF

The present invention provides novel moenomycin analogs as well as pharmaceutical compositions thereof, methods of synthesis, and methods of use in treating an infection by administering an inventive compound to a subject in need thereof. The moenomycin a

Efficient synthesis of core 2 class glycosyl amino acids by one-pot glycosylation approach

We describe the one-pot synthesis of core 2 class branched oligosaccharides initiated by chemo-selective glycosylation of silyl ether. Glycosylation of 6-O-silyl-4-benzyl-2-azido-thiogalactoside with glycosyl fluoride provided selectively 6-glycosylated thioglycoside without both O-glycosylation at the 3 position and S-glycosylation. Subsequent coupling of galactosyl fluoride and amino acids afforded the protected branched oligosaccharides in good yields.

Simplifying oligosaccharide synthesis: Efficient synthesis of lactosamine and siaylated lactosamine oligosaccharide donors

A practical sequence is described for converting D-glucosamine into peracetylated Gal(β-1,4)-GlcNTroc(β1-S)Ph and Neu5Ac(α-2,3)Gal(β-1,4)GlcNTroc(β1-S)Ph building blocks using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis. The known trichloroethoxycarbonyl, N-Troc, protecting group was selected as a suitable protecting group for both enzymatic and chemical reaction conditions. These oligosaccharide building blocks proved effective donors for the β-selective glycosylation of the unreactive OH-3 of a polymeric PEG-bound acceptor and for the axial OH-2 of a mannose acceptor in good yields. The resulting complex oligosaccharides are useful for vaccine and pharmaceutical applications.

Lipid A and related compounds. XXXII. Synthesis of biologically active N-acylated L-homoserine-containing D-glucosamine-4-phosphate derivatives structurally related to lipid A

New N-acylated L-homoserine-containing non-phosphorylated and phosphorylated D-glucosamine derivatives were synthesized as mimicks of lipid A disaccharide. Some of the synthesized compounds exhibited mitogenic activity and nitric oxide (NO) productivity.

Conversion of p-methoxyphenyl glycosides into the corresponding glycosyl chlorides and bromides, and into thiophenyl glycosides

p-Methoxyphenyl (pMP) β-D-glycopyranosides (Glc, Gal, GlcNPhth, GalNPhth, GlcNTroc, Galβ4Glc, Galα4Gal) were prepared from the corresponding 1-O-acetyl sugars in 79-90% yield, using boron trifluoride etherate as promoter. Treatment of the pMP glycosides with acyl chlorides or bromides in the presence of various Lewis acids gave the corresponding glycosyl chlorides and bromides in 81-98% yield. Treatment of the acyl-protected pMP glycosides with thiophenol and boron trifluoride etherate gave the corresponding thioglycosides in 80-100% yield and high (> 20:1) β/α selectivity. The stability of pMP glycosides was investigated against a series of reagents.