21193-75-9 | D-Galactal

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Description

• Catalog Number: AI44863
• Chemical Name: D-Galactal
• CAS Number: 21193-75-9
• Molecular Formula: C6H10O4
• Molecular Weight: 146.1412
• MDL Number: MFCD00038067
• SMILES: OC[C@H]1OC=C[C@H]([C@H]1O)O

Computed Properties

• Complexity: 134
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 3
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 3
• Rotatable Bond Count: 1
• XLogP3: -1

Upstream Synthesis Route

D-Galactal is a versatile compound that plays a significant role in chemical synthesis. As a carbohydrate derivative, D-Galactal is commonly used as a building block in the production of various pharmaceuticals, agrochemicals, and natural products. Its unique structure and reactivity make it a valuable intermediate in organic synthesis processes.In chemical synthesis, D-Galactal can serve as a precursor for the creation of complex molecules through various reactions such as glycosylation, oxidation, and reduction. Its ability to undergo selective transformations allows chemists to introduce specific functional groups at strategic positions, enabling the creation of intricate molecular structures with high precision.Moreover, D-Galactal's inherent chirality makes it a valuable tool in asymmetric synthesis, where the stereochemistry of the final product is critical. By utilizing D-Galactal as a chiral building block, chemists can access enantiomerically pure compounds with high efficiency and selectivity.Overall, the diverse applications of D-Galactal in chemical synthesis highlight its importance as a key component in the design and production of advanced materials and biologically active molecules.

Literature

• The synthesis of 2-deoxy-α-D-glycosides from D-glycals catalyzed by TMSI and PPh3.

  Carbohydrate research 20120901

• Measurement of the activity of individual subunits of single molecules of the tetrameric enzyme β-galactosidase.

  Analytical chemistry 20120515

• Sequential directed epoxydation-acidolysis from glycals with MCPBA. A flexible approach to protected glycosyl donors.

  The Journal of organic chemistry 20111202

• Convergent synthesis of the tetrasaccharide repeating unit corresponding to the O-antigen of the verotoxin-producing Escherichia coli O176.

  Glycoconjugate journal 20111201

• Stereodivergent synthesis of diastereoisomeric carba analogs of glycal-derived vinyl epoxides: a new access to carbasugars.

  Chirality 20111001

• A short and highly efficient synthesis of L-ristosamine and L-epi-daunosamine glycosides.

  Organic letters 20110218

• Stereoselective C-glycosidations with achiral and enantioenriched allenylsilanes.

  Organic letters 20101015

• Synthesis of gamma-aminobutyric acid analogs based on carbohydrate scaffolds.

  Carbohydrate research 20100616

• Regio- and stereocontrolled selective debenzylation and substitution reactions of C-2 formyl glycals. Application in the synthesis of constrained beta-sugar amino acids.

  The Journal of organic chemistry 20090807

• Attempts to improve the overall stereoselectivity of the Ireland-Claisen rearrangement.

  Organic letters 20090115

• Synthesis and self-assembly of glycal-based bolaforms.

  The Journal of organic chemistry 20081121

• The use of tri-O-acetyl-D-glucal and -D-galactal in the synthesis of omega-aminoalkyl 2-deoxy- and 2,3-dideoxy-d-hexopyranosides.

  Carbohydrate research 20081013

• Synthesis of new 2-phosphono-alpha-D-glycoside derivatives by stereoselective oxa-Michael addition to a D-galacto derived enone.

  Carbohydrate research 20080519

• 2-Nitroglycals: versatile intermediates for efficient and highly stereoselective base-catalyzed glycoside bond formations.

  Nature protocols 20080101

• Synthesis and anti-inflammatory activity of N-phthalimidomethyl 2,3-dideoxy- and 2,3-unsaturated glycosides.

  Carbohydrate research 20070702

• Glycal glycosylation and 2-nitroglycal concatenation, a powerful combination for mucin core structure synthesis.

  The Journal of organic chemistry 20070608

• Synthesis of a sialic acid alpha(2-3) galactose building block and its use in a linear synthesis of sialyl Lewis X.

  Organic letters 20070426

• Direct epoxidation of D-glucal and D-galactal derivatives with in situ generated DMDO.

  Carbohydrate research 20061127

• Antiproliferation and apoptosis induced by C-glycosides in human leukemia cancer cells.

  Bioorganic & medicinal chemistry letters 20060815

• Superoxide dismutase-like activity of cobalt(II) complexes based on a sugar platform.

  Chemical communications (Cambridge, England) 20051121

• Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals.

  The Journal of organic chemistry 20040903

• Reinvestigation of the mercuration-demercuration reaction on alkylated glycals: an improved method for the preparation of 2,3-dideoxy-alpha,beta-unsaturated carbohydrate enals.

  Carbohydrate research 20040802

• A novel sulfonamidoglycosylation of glycals.

  Organic letters 20031113

• Synthetic studies towards the tunicamycins and analogues based on diazo chemistry. Total synthesis of tunicaminyl uracil.

  Organic & biomolecular chemistry 20031107

• Totally stereoselective synthesis of 1,3-disaccharides through Diels-Alder reactions.

  The Journal of organic chemistry 20031031

• The use of tri-O-acetyl-D-glucal and -D-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides.

  Carbohydrate research 20021105

• Addition of malonyl radicals to glycals with C-1 acceptor groups: remarkable influence of the substituents on the product distribution.

  Chemical communications (Cambridge, England) 20020621

• Higher acyclic nitrogen containing deoxy sugar derivatives: a new lead in the generation of antimycobacterial chemotherapeutics.

  Bioorganic & medicinal chemistry 20020601

• [Clinical and experimental study of shuangcao tuihuang granule-1 in treating severe jaundice of acute icterohepatitis].

  Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine 20010901

• Protection of pig kidney (PK15) cells from the cytotoxic effect of anti-pig antibodies by alpha-galactosyl oligosaccharides.

  Transplantation 19940327