2873-29-2 | Tri-O-acetyl-D-Glucal

Packsize	Purity	Availability	Price	Discounted Price
5g	97%	in stock	$8.00	$5.00
10g	97%	in stock	$10.00	$7.00
25g	97%	in stock	$22.00	$15.00
100g	97%	in stock	$53.00	$37.00

Description

• Catalog Number: AB34946
• Chemical Name: Tri-O-acetyl-D-Glucal
• CAS Number: 2873-29-2
• Molecular Formula: C12H16O7
• Molecular Weight: 272.2512
• MDL Number: MFCD00063253
• SMILES: CC(=O)OC[C@H]1OC=C[C@H]([C@@H]1OC(=O)C)OC(=O)C

Computed Properties

• Complexity: 388
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 3
• Heavy Atom Count: 19
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• XLogP3: 0.2

Literature

• NaHSO(4) supported on silica gel: an alternative catalyst for Ferrier rearrangement of glycals.

  Carbohydrate research 20111129

• Synthesis and biological activity of the nucleoside analogs based on polyfluoroalkyl-substituted 1,2,3-triazoles.

  Nucleosides, nucleotides & nucleic acids 20111001

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

  Chirality 20111001

• Montmorillonite K-10 clay-catalyzed Ferrier rearrangement of 2-C-hydroxymethyl-d-glycals, 3,4,6-tri-O-alkyl-d-glycals, and 3,4-(dihydro-2H-pyran-5-yl)methanol: a few unexpected domino transformations.

  Carbohydrate research 20110927

• Total synthesis of landomycin A, a potent antitumor angucycline antibiotic.

  Journal of the American Chemical Society 20110817

• An efficient method for the selective synthesis of 2-deoxy-2-iodo-glycosides by O-glycosidation of D-glucal using I₂-Cu(OAc)₂.

  Carbohydrate research 20101102

• Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

  Bioorganic & medicinal chemistry letters 20101101

• Facile synthesis of enantiomerically pure 2- and 2,3-disubstituted furans catalysed by mixed Lewis acids: an easy route to 3-iodofurans and 3-(hydroxymethyl)furans.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20090608

• 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 novel migrastatin and dorrigocin A analogues from D-glucal.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20080101

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

  Carbohydrate research 20070702

• Cobaltpolyoxometalate-catalyzed cyclization of glucal with aryl amines: Synthesis of 2,4-disubstituted tetrahydroquinolines.

  Bioorganic & medicinal chemistry letters 20070515

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

  Carbohydrate research 20061127

• Exploring skeletal diversity via ring contraction of glycal-derived scaffolds.

  Organic letters 20061026

• A highly stereocontrolled total synthesis of (-)-neodysiherbaine A.

  The Journal of organic chemistry 20060526

• Two-step regio- and stereoselective syntheses of [19F]- and [18F]-2-deoxy-2-(R)-fluoro-beta-D-allose.

  Carbohydrate research 20060320

• 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

• A surprising dipolar cycloaddition provides ready access to aminoglycosides.

  Journal of the American Chemical Society 20040714

• A mild, efficient and alpha-selective glycosidation by using potassium dodecatungstocobaltate trihydrate as catalyst.

  Bioorganic & medicinal chemistry letters 20040705

• Synthesis of the C(1)-C(12) segment of peloruside A by an alpha-benzyloxymethyl ketone aldol strategy.

  Organic letters 20040304

• Electrochemical synthesis and X-ray crystal structures of beta-D-2-phenylselenyl-1,3,4,6-tetra-O-acetylglucopyranose and alpha-D-2-phenylselenyl-1,3,4,6-tetra-O-acetylmannopyranose.

  Carbohydrate research 20040102

• Trichloro-oxazolines as activated donors for aminosugar coupling.

  Organic letters 20031225

• Multigram synthesis of the C29-C51 subunit and completion of the total synthesis of altohyrtin C (spongistatin 2).

  Journal of the American Chemical Society 20031022

• 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

• Mild synthesis of disaccharidic 2,3-enopyranosyl cyanides and 2-C-2-deoxy pyranosyl cyanides with Hg(CN)(2)/HgBr(2)/TMSCN.

  The Journal of organic chemistry 20021101

• Stereoselective synthesis of a C-glycosylic compound (a 'methyl C-glycoside') through a regioselective free-radical ring-opening reaction. A single-crystal X-ray structure determination.

  Carbohydrate research 20020927

• Synthesis of enantiopure 3-azabicyclo[3.3.0]octen-7-one derivatives via intramolecular Pauson-Khand cycloaddition reaction using tri-O-acetyl-D-glucal as starting material.

  The Journal of organic chemistry 20020517

• Concise synthesis of ciguatoxin ABC-ring fragments and surface plasmon resonance study of the interaction of their BSA conjugates with monoclonal antibodies.

  Bioorganic & medicinal chemistry letters 20010806

• Synthesis of 1,2-unsaturated pyranosylphosphonate nucleosides from 3,4,6-tri-O-acetyl-D-glycal.

  Die Pharmazie 20010701

• Synthesis and hypolipidemic activity of N-phthalimidomethyl tetra-O-acyl-alpha-D-mannopyranosides.

  Carbohydrate research 20010604

• LiBF4-mediated C-glycosylation of glycals with allyltrimethylsilane: a facile synthesis of allyl C-glycosylic compounds.

  Carbohydrate research 20010518

• Synthesis and antiperoxidant activity of new phenolic O-glycosides.

  Carbohydrate research 20010227