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47622

Sigma-Aldrich

Fmoc-Thr(tBu)-OH

≥98.0% (HPLC)

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Synonym(s):
Fmoc-O-tert-butyl-L-threonine
Empirical Formula (Hill Notation):
C23H27NO5
CAS Number:
Molecular Weight:
397.46
Beilstein:
4581133
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

Quality Level

Assay

≥98.0% (HPLC)

optical activity

[α]20/D +16±1°, c = 1% in ethyl acetate

reaction suitability

reaction type: C-H Activation
reaction type: Fmoc solid-phase peptide synthesis
reagent type: ligand
reaction type: Peptide Synthesis

application(s)

peptide synthesis

functional group

Fmoc
amine
carboxylic acid

storage temp.

2-8°C

SMILES string

C[C@@H](OC(C)(C)C)[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(O)=O

InChI

1S/C23H27NO5/c1-14(29-23(2,3)4)20(21(25)26)24-22(27)28-13-19-17-11-7-5-9-15(17)16-10-6-8-12-18(16)19/h5-12,14,19-20H,13H2,1-4H3,(H,24,27)(H,25,26)/t14-,20+/m1/s1

InChI key

LZOLWEQBVPVDPR-VLIAUNLRSA-N

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This Item
473124731947517
Fmoc-Thr(tBu)-OH ≥98.0% (HPLC)

Sigma-Aldrich

47622

Fmoc-Thr(tBu)-OH

Fmoc-D-Thr(tBu)-OH ≥98.0% (TLC)

Sigma-Aldrich

47312

Fmoc-D-Thr(tBu)-OH

Fmoc-D-Tyr(tBu)-OH ≥98.0% (HPLC)

Sigma-Aldrich

47319

Fmoc-D-Tyr(tBu)-OH

Fmoc-Hyp(tBu)-OH ≥98.0% (HPLC)

Sigma-Aldrich

47517

Fmoc-Hyp(tBu)-OH

optical activity

[α]20/D +16±1°, c = 1% in ethyl acetate

optical activity

[α]20/D −15±1.5°, c = 1% in ethyl acetate

optical activity

-

optical activity

[α]20/D −25±2.5°, c = 1% in methanol

functional group

Fmoc, amine, carboxylic acid

functional group

Fmoc

functional group

Fmoc

functional group

Fmoc

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

reaction suitability

reaction type: C-H Activation

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

General description

Fmoc-Thr(tBu)-OH also known as Fmoc-O-tert-butyl-L-threonine, is commonly used as amino acid building block in peptide synthesis.

Application

Fmoc-Thr(tBu)-OH can be used to synthesize chlorofusin analogues via solid phase peptide synthesis. Additionally, it can serve as a protecting group for both the amine and the hydroxyl functions in solid-phase synthesis of complex depsipeptides.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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European Journal of Organic Chemistry, 2020, 183-192 (2020)
Solid-phase synthesis of chlorofusin analogues
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The Journal of Organic Chemistry, 72, 5146-5151 (2007)
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