1,2:5,6-Di-O-isopropylidene-α-D-gulofuranose

Name: 1,2:5,6-Di-O-isopropylidene-α-D-gulofuranose
Brand: ChemScene
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CAS No. 14686-89-6
Cat. No. CS-B1536
Purity≥98%
MDL No.MFCD00069693

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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1,2:5,6-Di-O-isopropylidene-α-D-gulofuranose|CS-B1536

Structure of 14686-89-6

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General Information

CAS No. 14686-89-6
Cat. No. CS-B1536
Purity ≥98%
MDL No. MFCD00069693
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₂₀O₆
Molecular Weight 260.28
Synonym(s) 1,2:5,6-Bis-O-(1-methylethylidene)-α-D-gulofuranose; Furo[2,3-d]-1,3-dioxole, α-D-gulofuranose deriv.; 1,2:5,6-Di-O-isopropylidene-alpha-D-gulofuranose
SMILES O[C@H]([C@H]([C@@H](CO1)OC1(C)C)O2)[C@@H](O3)[C@H]2OC3(C)C

Description

This α-D-gulofuranose derivative features two isopropylidene protecting groups at the 1,2- and 5,6-positions, providing exceptional stability and ease of handling in synthetic workflows. The configuration enables selective transformations at unmasked hydroxyl sites, facilitating efficient glycosylation sequences and enabling access to complex oligosaccharide architectures under standard conditions.

Application

1,2:5,6-Di-O-isopropylidene-α-D-gulofuranose serves as a stable, bench-ready chiral building block for carbohydrate chemistry, enabling selective functionalization at C3 and C4 positions. Its rigid cyclic acetal structure provides excellent protection for vicinal diols, facilitating stereoselective transformations in glycosylation and heterocycle synthesis. The compound exhibits high purity, ease of handling, and compatibility with standard organic protocols, making it ideal for the construction of complex oligosaccharides and bioactive scaffolds.

Synthesis

Route1
- 26775-14-4
- ~99%
- In-stock
  
  14686-89-6
References
- Raju, Ravinder; Castillo, Bernard F.; Richardson, Stewart K.; Thakur, Meena; Severins, Ryan; Kronenberg, Mitchell; Howell, Amy R. Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 15 p. 4122 - 4125
Route2
- 2847-00-9
- ~92%
- In-stock
  
  14686-89-6
References
- Drueckhammer, Dale G.; Wong, Chi-Huey Journal of Organic Chemistry, 1985 , vol. 50, # 26 p. 5912 - 5913
Route3
- 3253-75-6
- ~94%
- In-stock
  
  14686-89-6
References
- Masnovi, John; Koholic, Dolores J.; Berki, Robert J.; Binkley, Roger W. Journal of the American Chemical Society, 1987 , vol. 109, # 9 p. 2851 - 2853

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-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 66.38
LogP 0.3752
H_Acceptors 6
H_Donors 1
Rotatable_Bonds 1

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1,2:5,6-Di-O-isopropylidene-α-D-gulofuranose

CAS No. 14686-89-6

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