78184-40-4

Usage

Uses

Used in Pharmaceutical Development:
Allyl2,3,4-tri-O-benzyl-a-D-glucopyranoside is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with improved properties, such as enhanced solubility, stability, and bioavailability.
Used in Natural Product Synthesis:
In the field of natural product synthesis, Allyl2,3,4-tri-O-benzyl-a-D-glucopyranoside serves as a versatile building block for the construction of complex natural products. Its reactivity and functional groups enable the synthesis of a wide range of bioactive compounds with potential therapeutic applications.
Used in Organic Synthesis:
Allyl2,3,4-tri-O-benzyl-a-D-glucopyranoside is used as a valuable synthetic building block in organic synthesis. Its allyl and benzyl groups can be selectively modified or removed, allowing for the preparation of a variety of functionalized glucose derivatives with diverse applications in chemical research and industry.
Used in Chemical Research:
In chemical research, Allyl2,3,4-tri-O-benzyl-a-D-glucopyranoside is employed as a model compound to study various reaction mechanisms and to develop new synthetic methodologies. Its unique structure and reactivity make it an ideal candidate for exploring novel chemical transformations and understanding the underlying principles of organic reactions.

Upstream product

• 168608-17-1 allyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranoside 
• 87326-31-6 1-O-allyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 100-44-7 benzyl chloride 
• 107-18-6 allyl alcohol 
• 93382-48-0 allyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 103833-57-4 allyl 4,6-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 7464-56-4 1-O-allyl-α-D-glucopyranoside 
• 107242-80-8 1-O-allyl-6-O-trityl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 177554-96-0 allyl 2,3,4-tri-O-benzyl-6-O-methyl-α-D-glucopyranoside 
• 273935-08-3 allyl 2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranoside 
• 265312-91-2 1-O-allyl-2,3,4-tri-O-benzyl-6-O-(4-tolylsulfonyl)-α-D-glucopyranoside 
• 146773-71-9 allyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 177554-97-1 2,3,4-tri-O-benzyl-6-O-methyl-α-D-glucopyranose 
• 177555-03-2 2,3,4-tri-O-benzyl-6-O-methyl-α-D-glucopyranosyl bromide 
• 177555-10-1 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4-tri-O-benzyl-6-O-methyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 1253793-21-3 allyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1253793-20-2 allyl (2,3,4-tri-O-benzyl-α-D-xylopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1253793-24-6 allyl (2,3,4-tri-O-pivaloyl-β-D-xylopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1253793-12-2 C₅₇H₆₂O₁₀ 
• 1253793-26-8 allyl (2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1253793-13-3 allyl (2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1105543-55-2 1-O-(2',3',4'-tri-O-benzyl-6'-O-tosyl-α-D-glucopyranosyl)propan-1,3-diol 

Relevant academic research and scientific papers

Distribution and metabolism of 14C-sulfoquinovosylacylpropanediol (14C-SQAP) after a single intravenous administration in tumor-bearing mice

Sulfoquinovosylacylpropanediol (SQAP) is a novel potent radiosensitizer that inhibits angiogenesis in vivo and results in increased oxigenation and reduced tumor volume. We investigated the distribution, metabolism, and excretion of SQAP in male KSN-nude mice transplanted with a human pulmonary carcinoma, Lu65.For the metabolism analysis, a 2?mg (2.98?MBq)/kg of [glucose-U-14C]-SQAP (CP-3839) was intravenously injected. The injected SQAP was decomposed into a stearic acid and a sulfoquinovosylpropanediol (SQP) in the body.The degradation was relatively slow in the carcinoma tissue.1,3-propanediol[1-14C]-SQAP (CP-3635) was administered through intravenous injection of a 1?mg (3.48?MBq)/kg dose followed by whole body autoradiography of the mice.The autoradiography analysis demonstrated that SQAP rapidly distributed throughout the whole body and then quickly decreased within 4 hours except the tumor and excretion organs such as liver, kidney.Retention of SQAP was longer in tumor parts than in other tissues, as indicated by higher levels of radioactivity at 4 hours. The radioactivity around the tumor had also completely disappeared within 72 hours.

COMPOUND RETAINED IN TUMOR

A novel compound which specifically resides in a tumor, a method for allowing it to reside in a tumor, and a method for detecting, diagnosing, and treating tumor with use thereof are provided. The present invention relates to a compound represented by chemical formula (I) wherein R is an anionic group binding to hydrogen, R1 is OH, OCOH, OCO(CH2)hCH3, or an acting group, h being an integer of 0 or more, R2 is H, OH, OCOH, OCO(CH2)iCH3, or an acting group, i being an integer of 0 or more, R3 is OH, SO3H, or an acting group, R4 is OH, SO3H, or an acting group, and R5 is OH, SO3H, or an acting group, at least one of R1, R2, R3, R4, and R5 containing an acting group, or pharmaceutically acceptable salts thereof.

DIOXA-BICYCLO[3.2.1]OCTANE-2,3,4-TRIOL DERIVATIVES

Compounds of Formula (A) and (B) are described herein and the uses thereof for the treatment of diseases, conditions and/or disorders mediated by sodium-glucose transporter inhibitors (in particular, SGLT2 inhibitors).

Sulfonated sugar compounds, pharmaceutical compositions which contain the same, and methods of treating tumors with the same

Sulfoquinovosylacyl propanediol compounds represented by formula (I): wherein R1 is an acyl residue of a fatty acid, Y is a number of 1, 2 or 3, and M represents a cation having a positive charge equal to Y and pharmaceutically acceptable salts

Novel sulfoquinovosylacylglycerol derivative, and use thereof as medicaments

A method for immunosuppression in a subject comprising administering to the subject in need thereof, a pharmaceutically effective amount of at least one sulfoquinovosylacylglycerol derivative represented by General formula (1-1): wherein R101 represents an acyl residue of a higher fatty acid, and R102 represents a hydrogen atom or an acyl residue of a higher fatty acid; and a pharmaceutically acceptable salt thereof. Of the sulfoquinovosylacylglycerol derivatives, β-sulfoquinovosylacylglycerols are novel compounds. The present invention also relates to pharmaceutical composition comprising a pharmaceutically effective amount of the β-sulfoquinovosylacylglycerols and/or its pharmaceutically acceptable salt; and a pharmaceutically acceptable excipient. The pharmaceutical composition may be used as an immunosuppressive agent, anticancer agent and DNA polymerase α inhibitor.

Synthesis of sulfoquinovosylacylglycerols, inhibitors of eukaryotic DNA polymerase α and β

Sulfoquinovosyldiacylglycerols (SQDGs) and sulfoquinovosylmonoacylglycerols (SQMGs), bearing diverse fatty acids, were synthesized from d-glucose, and were examined for enzymatic inhibitions of DNA polymerase α and β. These results indicated that the carbon numbers of the fatty acids were highly related to the activities, at least in vitro, of eukaryotic DNA polymerase inhibition.

Synthesis and enzymatic evaluation of substrates and inhibitors of β-glucuronidases

The phosphono and the tetrazolyl analogues 4 and 5 of 4-methylumbelliferyl β-D-glucuronide (= (4-methyl-2-oxo-2H-1-benzopyran-7-yl β-D-glucopyranosid)uronic acid; 6) were synthesized and evaluated as substrates of β-glucuronidases. Similarly, the phenylcarbamate 7 and its phosphono analogue 8 were prepared and evaluated as inhibitors. To examine the diastereoselectivity of the phosphorylation, we also synthesized the protected L-ido-, D-gluco-, and D-galacto-configurated phospha-glycopyranuronates 12, 13, 21, 22, 34 and 35. Two strategies were followed. In the first one, the glucuronic acid 19 was decarboxylated to 11 and further transformed, via 20, into the trichloroacetimidate 10. Phosphorylation of 10 with (MeO)3P yielded the diastereoisomers 12 and 13, the diastereoselectivity depending on the solvent. In MeCN, 12 and 13 were obtained in a ratio of 1:1, while in non-participating solvents the L-ido 12 was by far the major diastereoisomer. The acetate 11 was inert to (MeO)3P, but reacted with (PhO)3P to the anomeric mixture 21/22, in keeping with a stabilizing 1,3-interaction in the intermediate phosphonium salt. Similarly, the phospha-galacturonates 34 and 35 were prepared from the galactoside 23 via the enol ether 26, the lactone 27, and the acetates 28/29 that were also transformed into the trichloroacetimidate 33. In the second, higher-yielding strategy, phosphorylation of the pentodialdehyde 39 to 40/41 was followed by hydrolysis and acetylation to the phospha-glucuronates 43/44. Transesterification to 45/46, selective deacetylation to 48/49, and formation of the trichloroacetimidates 50/51 were followed by glycosidation and deprotection to 4. The tetrazole 5 was prepared from the lactones 54/55 via the N-benzylamides 57/58 that were treated with TfN3 to give the N-benzyltetrazoles 59/60. These were transformed into the trichloroacetimidates 63/64, glycosylated to 65, and deprotected. The O-carbamoylhydroximo-lactone 7 derived from the glucuronate 67/68, and the phosphonate analogue 8 were prepared by established methods. The phosphonate 4 is slowly hydrolyzed by the E. coli β-glucuronidase, but neither 4 nor the tetrazole 5 are affected by the bovine liver β-glucuronidase. The phenylcarbamate 7 of D-glucarhydroximo-1,5-lactone, but not its phosphonate analogue 8, is an inhibitor (K(I) = 8 μM) of the E. coli β-glucuronidase. The bovine liver β-glucuronidase is inhibited strongly by 7 (IC50 = 0.2 μM) and weakly by 8 (IC50 = 2 mM).

109. Oligosaccharide analogues of polysaccharides: Part 8. Orthogonally protected cellobiose-derived dialkynes. A convenient method for the regioselective bromo- and protodegermylation of trimethylgermyl- and trimethylsilyl-protected dialkynes

The cellobiose-derived dialkynes 14 and 15 were prepared by glycosidation of the acceptor 9 with the thioglycosides 12 (82%) and 13 (85%), respectively. The acceptor 9 was prepared from the known alcohol 2 via the lactone 7 in five steps (48% overall), an