(3aR,6R,6aR)-6-(((tert-Butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol

Name: (3aR,6R,6aR)-6-(((tert-Butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol
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CAS No. 217309-46-1
Cat. No. CS-0197637
Purity≥95%
MDL No.None

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(3aR,6R,6aR)-6-(((tert-Butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol|CS-0197637

Structure of 217309-46-1

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General Information

CAS No. 217309-46-1
Cat. No. CS-0197637
Purity ≥95%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₈O₅Si
Molecular Weight 304.45
Synonym(s) 6-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol
SMILES CC(C)(C)[Si](C)(C)OC[C@@H]1[C@@H]2[C@H](C(O)O1)OC(C)(C)O2

Description

This tetrahydrofuro[3,4-d][1,3]dioxole features a silyl-protected hydroxyl group and a geminal dimethyl motif, enabling stable incorporation into complex carbohydrate syntheses. The tert-butyldimethylsilyl moiety provides robust protection under standard conditions, while the rigid fused ring system supports stereoselective transformations.

Application

(3aR,6R,6aR)-6-(((tert-Butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol serves as a stereochemically defined, bench-stable building block for complex carbohydrate and nucleoside synthesis. The silyl ether group provides robust protection of the C6 hydroxyl, enabling orthogonal deprotection in multi-step sequences. Its rigid tetrahydrofuro[3,4-d][1,3]dioxole core supports reliable glycosylation reactions and functions as a key intermediate in the construction of bioactive heterocyclic scaffolds requiring precise stereocontrol.

Safety Information

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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-P330-P362-P405-P501

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Computational Chemistry Data

TPSA 57.15
LogP 2.2455
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Tetrahydrofuran compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Dioxolane compounds

Key Words

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(3aR,6R,6aR)-6-(((tert-Butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol

CAS No. 217309-46-1

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