Lot numbers can be found on the outside label of a product:
(1R)-(1-Hydroxymethyl-but-3-enyl)-carbamic acid tert-butyl ester
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CAS No. 188359-85-5
- Cat. No. CS-0340688
- Purity≥97%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 188359-85-5
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General Information
- CAS No. 188359-85-5
- Cat. No. CS-0340688
- Purity ≥97%
- MDL No. None
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₀H₁₉NO₃
- Molecular Weight 201.26
- Synonym(s) Carbamic acid, [(1R)-1-(hydroxymethyl)-3-butenyl]-, 1,1-dimethylethyl ester
- SMILES O=C(OC(C)(C)C)N[C@@H](CO)CC=C
Description
This chiral building block features a hydroxymethyl-functionalized butenyl backbone paired with a tert-butyl carbamate protecting group. The (1R) stereochemistry ensures high enantioselectivity in downstream transformations, while the pendant hydroxyl and alkene moieties enable selective derivatization. Bench-stable and moisture-tolerant, it integrates seamlessly into complex molecule synthesis workflows.
Application
(1R)-(1-Hydroxymethyl-but-3-enyl)-carbamic acid tert-butyl ester serves as a versatile chiral building block for synthesizing functionalized pyrrolidines and other nitrogen-containing heterocycles. The terminal alkene enables palladium-catalyzed coupling reactions, while the protected carbamate and allylic hydroxyl group offer orthogonal reactivity. Bench-stable and amenable to standard purification protocols, it facilitates efficient access to complex scaffolds in medicinal chemistry campaigns.
Synthesis
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Route1
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In-stock
24424-99-5 - ~%
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In-stock
188359-85-5
References
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Matsunaga, Hirofumi; Ishizuka, Tadao; Kunieda, Takehisa Tetrahedron, 1997 , vol. 53, # 4 p. 1275 - 1294
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Route2
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188347-88-8 - ~%
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In-stock
188359-85-5
References
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Matsunaga, Hirofumi; Ishizuka, Tadao; Kunieda, Takehisa Tetrahedron, 1997 , vol. 53, # 4 p. 1275 - 1294
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Route3
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In-stock
54594-06-8 - ~%
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In-stock
188359-85-5
References
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PHENEX PHARMACEUTICALS AG; KINZEL, Olaf; STEENECK, Christoph; KLEYMANN, Gerald; ALBERS, Michael; HOFFMANN, Thomas; KREMOSER, Claus; PEROVIC-OTTSTADT, Sanja; SCHLUeTER, Thomas Patent: WO2011/107248 A1, 2011 ; WO 2011/107248 A1
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P280-P302+P352
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Quality Control
Computational Chemistry Data
- TPSA 58.56
- LogP 1.4481
- H_Acceptors 3
- H_Donors 2
- Rotatable_Bonds 4
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Key Words
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