trans-tert-Butyl (3-hydroxycyclobutyl)carbamate

Name: trans-tert-Butyl (3-hydroxycyclobutyl)carbamate
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CAS No. 389890-42-0
Cat. No. CS-0038605
Molecule weight187.24
Purity≥98%
MDL No.MFCD09038209

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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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trans-tert-Butyl (3-hydroxycyclobutyl)carbamate|CS-0038605

Structure of 389890-42-0

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General Information

CAS No. 389890-42-0
Cat. No. CS-0038605
Purity ≥98%
MDL No. MFCD09038209
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₇NO₃
Molecular Weight 187.24
Synonym(s) trans-3-AMintocyclobutanol
SMILES CC(C)(C)OC(=O)N[C@H]1C[C@@H](C1)O

Description

trans-tert-Butyl (3-hydroxycyclobutyl)carbamate is a bench-stable, moisture-tolerant carbamate protecting group for alcohols. This rigid cyclobutane scaffold imparts conformational control, enabling selective functionalization in complex molecule synthesis. The tertiary butyl moiety facilitates mild deprotection under acidic conditions.

Application

trans-tert-Butyl (3-hydroxycyclobutyl)carbamate serves as a stable, bench-friendly chiral auxiliary for cyclobutane-based synthesis. The protected hydroxyl group enables selective transformations while the carbamate handles orthogonally in multistep sequences. It functions effectively in stereoselective functionalization and cyclobutane scaffold construction, offering predictable reactivity and straightforward purification.

Synthesis

Route1
- 1036260-45-3
- In-stock
  
  24424-99-5
- ~%
- In-stock
  
  389890-42-0
References
- GLAXO GROUP LIMITED Patent: WO2007/62333 A2, 2007 ; Location in patent: Page/Page column 13 ;
Route2
- 871014-16-3
- ~62%
- In-stock
  
  389890-42-0
References
- Radchenko, Dmytro S.; Pavlenko, Sergiy O.; Grygorenko, Oleksandr O.; Volochnyuk, Dmitriy M.; Shishkina, Svitlana V.; Shishkin, Oleg V.; Komarov, Igor V. Journal of Organic Chemistry, 2010 , vol. 75, # 17 p. 5941 - 5952

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

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Computational Chemistry Data

TPSA 58.56
LogP 1.0344
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Alcohol

Building Blocks Skeleton Fatty ring compounds Cyclobutane compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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trans-tert-Butyl (3-hydroxycyclobutyl)carbamate

CAS No. 389890-42-0

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