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(4S,5R)-4-[(tert-Butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-one

  • CAS No. 83159-91-5

  • Cat. No. CS-0053171
  • Purity≥95%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

(4S,5R)-4-[(tert-Butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-one|CS-0053171

Structure of 83159-91-5

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General Information

  • CAS No. 83159-91-5
  • Cat. No. CS-0053171
  • Purity ≥95%
  • MDL No. None
  • Storage Store at room temperature, keep dry and cool
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₇H₃₆O₄Si₂
  • Molecular Weight 360.64
  • Synonym(s) 3,5-Di-O-(tert-butyldimethylsilyl)-2-deoxy-D-ribonolactone
  • SMILES CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)C[C@@H]1O[Si](C)(C)C(C)(C)C

Description

This silyl-protected oxolane derivative features two tert-butyldimethylsilyl ether groups strategically positioned to stabilize reactive hydroxyl functionalities. The (4S,5R) stereochemistry ensures precise spatial control for downstream synthetic applications. Bench-stable and moisture-tolerant, it integrates seamlessly into complex molecule assembly workflows, particularly in carbohydrate and nucleoside analog synthesis.

Application

(4S,5R)-4-[(tert-Butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-one serves as a stereochemically defined, silyl-protected diol precursor in complex carbohydrate and natural product synthesis. Its bench-stable structure enables reliable protection of vicinal hydroxyl groups with orthogonal deprotection profiles, facilitating sequential functionalization in multi-step routes. The molecule functions as a key building block for oxolane-based scaffolds, offering predictable reactivity in glycosylation and coupling reactions under standard conditions.

Synthesis

  • Route1
    • null|null
      18162-48-6
    • In-stock
      (4S,5R)-4-Hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one|CS-0053170
      34371-14-7
    • ~95%
    • In-stock
      (4S,5R)-4-[(tert-Butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-one|CS-0053171
      83159-91-5

    References

    • Kozikowski,, Alan P.; Ghosh, Arun K. Journal of Organic Chemistry, 1984 , vol. 49, # 15 p. 2762 - 2772
  • Route2
    • null|null
      83159-90-4
    • ~%
    • In-stock
      (4S,5R)-4-[(tert-Butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-one|CS-0053171
      83159-91-5

    References

    • Agricultural and Biological Chemistry, , vol. 49, # 5 p. 1435 - 1440
  • Route3
    • In-stock
      (4S,5R)-4-Hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one|CS-0053170
      34371-14-7
    • null|null
      18162-48-6
    • ~67%
    • null|null
      106183-56-6
    • In-stock
      (4S,5R)-4-[(tert-Butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-one|CS-0053171
      83159-91-5

    References

    • Danilova, G. A.; Mel'nikova, V. I.; Pivnitsky, K. K. Tetrahedron Letters, 1986 , vol. 27, # 22 p. 2489 - 2490

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319
Precautionary Statements : P261-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   44.76
  • LogP   4.7141
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   5

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