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Atomfair 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone C34H34O6 CAS 13096-62-3

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone (CAS No. 13096-62-3) is a highly specialized carbohydrate derivative with the molecular formula C34H34O6. This compound is a key intermediate in synthetic organic chemistry, particularly in the preparation of complex sugars and glycoconjugates. The tetra-O-benzyl protection ensures selective reactivity, making it invaluable for controlled glycosylation reactions. With a purity of ≥95%, this white to off-white crystalline powder is rigorously tested via HPLC, NMR, and MS to meet the stringent requirements of pharmaceutical and biochemical research. Store under inert conditions (2-8°C) to maintain stability.

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Description

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone (CAS No. 13096-62-3) is a highly specialized carbohydrate derivative with the molecular formula C34H34O6. This compound is a key intermediate in synthetic organic chemistry, particularly in the preparation of complex sugars and glycoconjugates. The tetra-O-benzyl protection ensures selective reactivity, making it invaluable for controlled glycosylation reactions. With a purity of ≥95%, this white to off-white crystalline powder is rigorously tested via HPLC, NMR, and MS to meet the stringent requirements of pharmaceutical and biochemical research. Store under inert conditions (2-8°C) to maintain stability.

Properties

  • CAS Number: 13096-62-3
  • Complexity: 705
  • IUPAC Name: (3R,4S,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-one
  • InChI: InChI=1S/C34H34O6/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-33H,21-25H2/t30-,31-,32+,33-/m1/s1
  • InChI Key: BUBVLQDEIIUIQG-NXVJRICRSA-N
  • Exact Mass: 538.23553880
  • Molecular Formula: C34H34O6
  • Molecular Weight: 538.6
  • SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H]([C@H](C(=O)O2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
  • Topological: 63.2
  • Monoisotopic Mass: 538.23553880
  • Synonyms: 13096-62-3, 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone, (3R,4S,5R,6R)-3,4,5-TRIS(BENZYLOXY)-6-((BENZYLOXY)METHYL)TETRAHYDRO-2H-PYRAN-2-ONE, D-Gluconic acid, 2,3,4,6-tetrakis-O-(phenylmethyl)-, delta-lactone, 2,3,4,6-Tetra-O-benzyl-D-gluconic acid-delta-lactone, (3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-one, MFCD08703228, (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-one, 2,3,4,6-tetra-o-benzyl-d-(+)-glucono-1,5-lactone, BUBVLQDEIIUIQG-NXVJRICRSA-N, SCHEMBL500473, DTXSID20447897, AKOS015918438, Tetra-O-benzyl-delta-D-Gluconolactone, AC-1439, CS-W005485, HY-W005485, MT04993, AS-19520, T3793, 2,3,4,6-tetra-o-benzyl-glucono-1,5-lactone, D-Gluconic acid, 2,3,4,6-tetrakis-O-(phenylmethyl)-, |A-lactone, (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxylmethyl)tetrahydro-2H-pyran-2-one, (3r,4s,5r,6r)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydropyran-2-one, (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one, 2,3,4,6-Tetra-O-benzyl-D-gluconic acid-delta-lactone;(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)tetrahydropyran-2-one, D-Gluconic acid, 2,3,4,6-tetrakis-O-(phenylmethyl)-, d-lactone (9CI, ACI); Gluconic acid, 2,3,4,6-tetra-O-benzyl-, d-lactone, D- (8CI); (3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one; (3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6

This compound is widely used as a protected sugar lactone in the synthesis of glycosides, oligosaccharides, and glycodendrimers. It serves as a critical precursor in medicinal chemistry for developing glycosidase inhibitors and antiviral agents. Researchers also employ it in carbohydrate-based drug discovery and glycoengineering applications.

Safety and Hazards

GHS Hazard Statements

  • H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
  • H413 (100%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statements

  • P264, P270, P273, P301+P317, P330, and P501

Hazard Classes and Categories

  • Acute Tox. 4 (100%)
  • Aquatic Chronic 4 (100%)

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Disclaimer

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  • Strictly prohibited: Resale, repackaging, or formulation into commercial products.
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