(3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid

Name: (3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 54622-95-6
Cat. No. CS-0064750
Purity≥97%
MDL No.MFCD10039832

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(3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid|CS-0064750

Structure of 54622-95-6

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General Information

CAS No. 54622-95-6
Cat. No. CS-0064750
Purity ≥97%
MDL No. MFCD10039832
Storage 4°C, protect from light, stored under argon
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₄O₆
Molecular Weight 218.20
Synonym(s) Methyl 2,3-O-isopropylidene-beta-D-ribofuranosiduronic acid
SMILES OC([C@@H]1[C@]2([H])[C@](OC(C)(C)O2)([H])[C@H](OC)O1)=O

Description

This tetrahydrofuran derivative features a methoxy-substituted dioxole ring system with a carboxylic acid at the 4-position, delivering enhanced solubility and stability. The stereochemistry at C3a, C4, C6, and C6a positions ensures precise spatial orientation for chiral synthesis. Its bench-stable nature and moisture-tolerant functionality simplify handling in complex reaction sequences.

Application

(3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid serves as a stereochemically defined building block for the synthesis of complex heterocyclic scaffolds. Its constrained tetrahydrofuran core with orthogonal protecting groups enables selective transformations in multi-step sequences. The carboxylic acid functionality facilitates coupling reactions, while the methoxy and gem-dimethyl substituents provide enhanced stability and modulate reactivity, making it well-suited for iterative synthetic approaches in medicinal chemistry and natural product synthesis.

Synthesis

Route1
- In-stock
  
  4099-85-8
- ~97%
- In-stock
  
  54622-95-6
References
- Huang, Lijun; Teumelsan, Nardos; Huang, Xuefei Chemistry - A European Journal, 2006 , vol. 12, # 20 p. 5246 - 5252
Route2
- 532-20-7
- ~%
- In-stock
  
  54622-95-6
References
- Journal of Medicinal Chemistry, , vol. 47, # 16 p. 4041 - 4053
Route3
- 67814-68-0
- ~%
- In-stock
  
  54622-95-6
References
- Journal of Medicinal Chemistry, , vol. 47, # 16 p. 4041 - 4053

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 74.22
LogP -0.0376
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Dioxolane compounds

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(3aS,4S,6R,6aR)-6-Methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid

CAS No. 54622-95-6

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