Lot numbers can be found on the outside label of a product:
(3R,4R,5R)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate
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CAS No. 28708-32-9
- Cat. No. CS-W005013
- Purity≥97%
- MDL No.MFCD03788309
*For research and further manufacturing use only, not for direct human use.
Structure of 28708-32-9
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General Information
- CAS No. 28708-32-9
- Cat. No. CS-W005013
- Purity ≥97%
- MDL No. MFCD03788309
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₃H₁₈O₉
- Molecular Weight 318.28
- Synonym(s) None
- SMILES O=C(OC[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(C)=O)C(OC(C)=O)O1)C
Description
This triacetate derivative of tetrahydrofuran triol serves as a key protecting group strategy in carbohydrate synthesis, offering enhanced stability and controlled deprotection under mild conditions. The (3R,4R,5R) stereochemistry ensures predictable stereoselective transformations, while the acetoxymethyl side chain enables selective functionalization.
Application
(3R,4R,5R)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate serves as a key chiral building block in the synthesis of complex carbohydrate derivatives and nucleoside analogs. Its triacetate functionality provides enhanced stability and facilitates selective deprotection sequences, enabling controlled access to diol intermediates. The molecule exhibits excellent bench stability and functional group tolerance, allowing straightforward integration into multi-step syntheses involving glycosylation, coupling, or cyclization reactions.
Synthesis
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Route1
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532-20-7 -
108-24-7 - ~99%
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In-stock
28708-32-9
References
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Li, Lingjun; Lin, Baichuan; Yang, Zhenjun; Zhang, Liangren; Zhang, Lihe Tetrahedron Letters, 2008 , vol. 49, # 29-30 p. 4491 - 4493
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Route2
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37077-80-8
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108-24-7
- ~73%
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In-stock
28708-32-9
References
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Cen, Yana; Sauve, Anthony A. Journal of the American Chemical Society, 2010 , vol. 132, # 35 p. 12286 - 12298
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Route3
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52554-28-6 -
108-24-7
- ~%
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In-stock
28708-32-9
References
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Liav, Avraham; Angala, Shiva K.; Brennan, Patrick J.; Jackson, Mary Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 8 p. 2649 - 2651
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 114.43
- LogP -0.2991
- H_Acceptors 9
- H_Donors 0
- Rotatable_Bonds 5
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Key Words
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