Benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate

Name: Benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate
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CAS No. 274693-54-8
Cat. No. CS-M2434
Molecule weight351.39
Purity≥97%
MDL No.None

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Benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate|CS-M2434

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General Information

CAS No. 274693-54-8
Cat. No. CS-M2434
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₂₅NO₆
Molecular Weight 351.39
Synonym(s) N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester
SMILES O=C(OCC1=CC=CC=C1)N[C@@H]2C[C@H](OCCO)[C@]3([H])[C@@]2([H])OC(C)(C)O3

Description

Benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate features a rigid cyclopenta[d][1,3]dioxole core with a bench-stable, moisture-tolerant carbamate handle. This configuration enables direct incorporation into oligonucleotide synthesis workflows without protecting group manipulation.

Application

Benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate serves as a stable, bench-ready chiral building block for the synthesis of complex heterocyclic scaffolds. Its protected hydroxyl and carbamate functionalities enable orthogonal reactivity in multi-step syntheses, facilitating selective transformations under mild conditions. The cyclopentane-dioxolane core provides rigidity and stereocontrol, making it valuable in medicinal chemistry campaigns requiring defined stereogenic centers.

Synthesis

Route1
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  274693-54-8
References
- Zhang, Hao; Liu, Jun; Zhang, Luyong; Kong, Lingyi; Yao, Hequan; Sun, Hongbin Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 11 p. 3598 - 3602

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 86.25
LogP 1.5827
H_Acceptors 6
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Dioxolane compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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Benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate

CAS No. 274693-54-8

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