Boc-Thr-OH | N-protective Amino Acid

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Quality Control of Boc-Thr-OH Purity: 95% SDS Specification

COA

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NMR

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CNMR

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HPLC

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LC-MS

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Product Details of Boc-Thr-OH

CAS No. :	2592-18-9
Formula :	C₉H₁₇NO₅
M.W :	219.24
SMILES Code :	C[C@@H](O)[C@@H](C(O)=O)NC(OC(C)(C)C)=O
Synonyms :	Boc-Thr-OH
MDL No. :	MFCD00065946
InChI Key :	LLHOYOCAAURYRL-RITPCOANSA-N
Pubchem ID :	2724766

Safety of Boc-Thr-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Boc-Thr-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 2592-18-9 ]

[ 2592-18-9 ] Synthesis Path-Downstream 1~35

1
[ 24498-31-5 ]
[ 2592-18-9 ]
[ 23010-46-0 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1969,vol. 311,p. 490 - 496.

2
[ 589-57-1 ]
[ 2592-18-9 ]
[ 109539-05-1 ]

References: [1]Synthesis,1986,p. 572 - 573.

3
[ 28954-12-3 ]
[ 24424-99-5 ]
[ 2592-18-9 ]

Yield	Reaction Conditions	Operation in experiment
304 mg	With sodium hydrogencarbonate; In methanol; water; at 0 - 20℃; for 18h;	Preparation 43 (2S,3S)-2-((ferf-Butoxycarbonyl)amino)-3-hvdroxybutanoic acid Di-terf-butyldicarbonate (550 mg, 2,52 mmol) was added to a mixture of L-allo- threonine (250 mg, 2.10 mmol) and sodium bicarbonate (529 mg, 6.30 mmol) in methanol (2.5 ml_) and water (2.5 ml_) at 0°C. The reaction mixture was then allowed to warm to room temperature and stirred at room temperature for 18 hours. The reaction mixture was concentrated to remove methanol and the residual aqueous phase was acidified with 6N hydrochloric acid solution (pH 3~ 4), extracted with ether (3x), the organic phases were combined and washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo, then dried under vacuum for 24 hours to afford the title compound (304 mg) as a white solid. LCMS Rt= 0.36 minutes MS m/z 220 [M+H]+ MS m/z 218 [M-H]-

References: [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 6935 - 6960.
[2]Journal of the American Chemical Society,2000,vol. 122,p. 10214 - 10215.
[3]Journal of the American Chemical Society,2003,vol. 125,p. 1877 - 1887.
[4]Patent: WO2019/52545,2019,A1 .Location in patent: Paragraph 00300.
[5]Journal of Organic Chemistry,1982,vol. 47,p. 5160 - 5167.
[6]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4329 - 4332.
[7]Journal of the American Chemical Society,2002,vol. 124,p. 2534 - 2543.
[8]Journal of Medicinal Chemistry,2012,vol. 55,p. 4824 - 4836.
[9]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 6134 - 6143.
[10]Patent: WO2013/114250,2013,A1 .Location in patent: Page/Page column 158; 159.
[11]Angewandte Chemie - International Edition,2015,vol. 54,p. 1284 - 1288.
Angew. Chem.,2015,vol. 127,p. 1300 - 1304,5.
[12]Journal of Medicinal Chemistry,2015,vol. 58,p. 4204 - 4219.
[13]European Journal of Organic Chemistry,2018,vol. 2018,p. 1465 - 1476.

4
[ 2592-18-9 ]
[ 593-56-6 ]
[ 80543-39-1 ]

References: [1]Journal of Organic Chemistry,1982,vol. 47,p. 5160 - 5167.

5
[ 2592-18-9 ]
[ 101924-87-2 ]
[ 102408-95-7 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 5159 - 5162.

6
[ 2592-18-9 ]
[ 101924-86-1 ]
[ 102409-04-1 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 5159 - 5162.

7
[ 2592-18-9 ]
[ 101924-82-7 ]
[ 101924-73-6 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 5155 - 5158.

8
[ 2592-18-9 ]
[ 106369-53-3 ]
[ 101924-83-8 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 5155 - 5158.

9
[ 2592-18-9 ]
[ 101924-80-5 ]
[ 101924-72-5 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 5155 - 5158.

10
[ 2592-18-9 ]
[ 106930-61-4 ]
[ 108312-46-5 ]

References: [1]Tetrahedron Letters,1986,vol. 27,p. 2653 - 2656.

11
[ 2592-18-9 ]
[ 119973-54-5 ]

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 2311 - 2316.

12
[ 69739-34-0 ]
[ 2592-18-9 ]
[ 308279-72-3 ]

Yield	Reaction Conditions	Operation in experiment
78%		Example 1: Synthesis of Compound of Formula IIIQH O 1. TBSOTf, Et3N TBSO OX U CH2Cl2, 0°C, 2h ^I O. 2. K2CO3, MeOH/H2O iNHBoc 2 h, 23°C, 78percent NHBoc 3. PhSH, DCC, HOBtCompound Al EtOAc, 23°C, 12h Compound A2 69percent yield; >;99.9percent eeN-Boc-L-allo-threonine (Compound Al; synthesized from L-allo-threonine purchased from Fluka Chemical Corp.; Milwaukee, WI) was protected with TBS using te/t-butyldimethylsilyl triflate (TBSOTf) and then treated with thiophenol (PhSH), JV,jV-dicyclohexylcarbodiimide (DCC), and 1-hydroxybenzotriazole (HOBt) in ethyl acetate (EtOAc) to form (2S,3S)-S-phenyl 2-(te/t-butoxycarbonylamino)-3- (tetaut-butyldimethylsilyloxy)butanethioate (Compound A2). Compound A2 was formed in 69percent yield and an enantiomeric excess (ee) of >;99.9percent.

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 10214 - 10215.
[2]Patent: WO2010/85547,2010,A2 .Location in patent: Page/Page column 17.

13
[ 2592-18-9 ]
(S)-allylglycine methyl ester hydrochloride [ No CAS ]
N-tert-butoxycarbonyl-(2S,3S)-threonyl-(S)-allylglycine methyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 1871 - 1882.

14
[ 2592-18-9 ]
[ 2462-32-0 ]
[ 437631-41-9 ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 1877 - 1887.

15
[ 2592-18-9 ]
[ 42854-62-6 ]
[ 947189-54-0 ]