ChemicalBook > CAS DataBase List > N-(tert-Butoxycarbonyl)-L-glutamine

N-(tert-Butoxycarbonyl)-L-glutamine

Product Name
N-(tert-Butoxycarbonyl)-L-glutamine
CAS No.
13726-85-7
Chemical Name
N-(tert-Butoxycarbonyl)-L-glutamine
Synonyms
BOC-GLN;BOC-L-GLUTAMINE;BOC-L-GLN;n-OH;BOC-L-GLN-OH;NSC 334370;BOC-GLUTAMINE;Boc-Gln-OH 98%;TBOC-L-GLUTAMINE;N-t-BOC-L-Gln-OH
CBNumber
CB8436290
Molecular Formula
C10H18N2O5
Formula Weight
246.26
MOL File
13726-85-7.mol
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N-(tert-Butoxycarbonyl)-L-glutamine Property

Melting point:
113-116 °C (dec.)(lit.)
alpha 
-3.5 º (c=2,C2H5OH)
Boiling point:
389.26°C (rough estimate)
Density 
1.2430 (rough estimate)
refractive index 
-4 ° (C=2, EtOH)
storage temp. 
Sealed in dry,2-8°C
solubility 
Soluble in DMSO and methanol. Soluble in 1 mmole in 2 ml DMF.
form 
Solid
pka
3.84±0.10(Predicted)
color 
White
optical activity
[α]20/D 3.5°, c = 1 in ethanol
BRN 
2127805
InChI
InChI=1S/C10H18N2O5/c1-10(2,3)17-9(16)12-6(8(14)15)4-5-7(11)13/h6H,4-5H2,1-3H3,(H2,11,13)(H,12,16)(H,14,15)/t6-/m0/s1
InChIKey
VVNYDCGZZSTUBC-LURJTMIESA-N
SMILES
C(O)(=O)[C@H](CCC(N)=O)NC(OC(C)(C)C)=O
CAS DataBase Reference
13726-85-7(CAS DataBase Reference)
EPA Substance Registry System
L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]- (13726-85-7)
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
TSCA 
Yes
HS Code 
29241990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
408441
Product name
Boc-Gln-OH
Purity
98%
Packaging
25g
Price
$146
Updated
2025/07/31
TCI Chemical
Product number
B1649
Product name
Nalpha-(tert-Butoxycarbonyl)-L-glutamine
Purity
>98.0%(HPLC)(T)
Packaging
10g
Price
$67
Updated
2025/07/31
TCI Chemical
Product number
B1649
Product name
Nalpha-(tert-Butoxycarbonyl)-L-glutamine
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$132
Updated
2025/07/31
Usbiological
Product number
005155
Product name
tert-Butoxycarbonyl-L-glutamine
Packaging
1g
Price
$319
Updated
2021/12/16
TRC
Product number
B690430
Product name
tert-Butoxycarbonyl-L-glutamine
Packaging
100g
Price
$325
Updated
2021/12/16
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N-(tert-Butoxycarbonyl)-L-glutamine Chemical Properties,Usage,Production

Chemical Properties

White fine crystalline powder

Uses

Protected Glutamine.

Uses

It is employed in the synthesis and analgesic activity of human .beta.-endorphin.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

56-85-9

24424-99-5

13726-85-7

Example 1: Synthesis of N-(Boc)-L-glutamine (1): L-glutamine (25 g, 0.17 mol) was dissolved in 300 mL of aqueous NaOH solution (21.9 g, 0.547 mol). The resulting solution was cooled to below 10 °C, followed by the slow addition of a THF (150 mL) solution of Boc anhydride (0.205 mol) (note that the reaction is exothermic). The reaction mixture was stirred continuously at 25 °C for 20 hours. The progress of the reaction was monitored by TLC and the unfolding agent was MeOH:CH2Cl2 (1:1, containing 0.1% AcOH). Upon completion of the reaction, the organic phase was separated and the aqueous phase was extracted with hexane (100 mL) and acidified to pH 2 with 2N HCl, followed by extraction with ethyl acetate (2 x 250 mL). The organic phases were combined, dried with Na2SO4 and the solvent was evaporated in vacuum. The resulting viscous oily product was diluted with dichloromethane and evaporated again. After standing for 2-3 days, it was crystallized from hexane to give N-(Boc)-L-glutamine (1) (37.5 g, 89% yield) as a colorless solid. The product was characterized by 1H NMR (DMSO, 300 MHz) and ESI-MS (m/z: 269 [M+Na]+).

References

[1] Journal of the American Chemical Society, 1997, vol. 119, # 17, p. 4086 - 4087
[2] Patent: WO2015/189856, 2015, A1. Location in patent: Page/Page column 14
[3] Synthetic Communications, 2008, vol. 38, # 2, p. 162 - 169
[4] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 8, p. 2777 - 2780
[5] Organic Syntheses, 1985, vol. 63, p. 160 - 160

N-(tert-Butoxycarbonyl)-L-glutamine Preparation Products And Raw materials

Raw materials

Preparation Products

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N-(tert-Butoxycarbonyl)-L-glutamine Suppliers

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View Lastest Price from N-(tert-Butoxycarbonyl)-L-glutamine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Boc-L-Gln-OH 13726-85-7
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98%min
Supply Ability
500kgs
Release date
2021-09-24
Sichuan HongRi Pharma-Tech Co.,Ltd
Product
Boc-L-Gln-OH 13726-85-7
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1T+
Release date
2023-09-25
Anhui Dexinjia Biopharm Co., Ltd
Product
N-(tert-Butoxycarbonyl)-L-glutamine 13726-85-7
Price
US $10.00/kg
Min. Order
1kg
Purity
98
Supply Ability
100kg
Release date
2024-04-10

13726-85-7, N-(tert-Butoxycarbonyl)-L-glutamineRelated Search:

BOC-L-Serine BOC-L-Asparagine Boc-D-Valine BOC-CYS-OH L-Glutamine Boc-L-Glutamic acid 4-BROMO-2,2-DIPHENYLBUTYRONITRILE 5-Methoxymethyl-2,3-pyridinedicarboxylic acid (2,3,4-trihydroxy-5-oxo-pentoxy)phosphonic acid BUTOXYCARBOXIM 1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one L-Glutamic acid, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]formylamino]benzoyl]-, 1-(1,1-dimethylethyl) 5-methyl ester NALPHA-(TERT-BUTOXYCARBONYL)-D-GLUTAMINE,N-tert-Butoxycarbonyl-D-glutamine ,n(à)-tert-butoxycarbonyl-d-glutamine N-Boc-N'-(9-xanthenyl)-L-glutamine N-(tert-Butoxycarbonyl)-L-glutamine N-Boc-N'-trityl-L-glutamine NALPHA-tert-Butoxycarbonyl-L-glutamine 4-nitrophenyl ester BOC-N-GAMMA-ETHYL-L-GLUTAMINE

  • n2-[(1,1-dimethylethoxy)carbonyl]-l-glutamin
  • BOC-GLN
  • BOC-GLUTAMINE
  • (S)-5-AMINO-2-(TERT-BUTOXYCARBONYLAMINO)-5-OXOPENTANOIC ACID
  • N(ɑ)-Boc-L-glutamine, 98+%
  • BOC-L-GLUTAMINE extrapure
  • Boc-L-glutamine, Nα-(tert-Butoxycarbonyl)-L-glutamine
  • L-Glutamine, N(2)-[(1,1-dimethylethoxy)carbonyl]-
  • N-(tert-Butoxycarbonyl)-3-(carbamoylmethyl)alanine
  • N2-[(1,1-Dimethylethoxy)carbonyl]-L-glutamine
  • Nα-(tert-Butyloxycarbonyl)-L-glutamine
  • N(^a)-Boc-L-glutamine, 98+%
  • tert-Butoxycarbonyl-L-glutamine
  • Nα- (tert-Butoxycarbonyl)-L-glutamine ,99%
  • Boc-Gln-OH,Nα-(tert-Butoxycarbonyl)-L-glutamine, Boc-L-glutamine
  • L-GLUTAMINE-N-T-BOC
  • BOC-L-GlutaMine(Boc-L-Gln-OH)
  • Boc-Gln-OH (Boc-L-GlutaMine
  • Na-(tert-Butoxycarbonyl)-L-glutaMine)
  • N(alpha)-Boc-L-glutamine, 98+%
  • (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-carbamoylbutanoic acid
  • N-[amino(methoxy)methylidene]carbamic acid tert-butyl ester
  • n-OH
  • BOC-L-GLUTAMINE
  • BOC-L-GLN
  • BOC-L-GLN-OH
  • TBOC-L-GLUTAMINE
  • T-BUTYLOXYCARBONYL-L-GLUTAMINE
  • N(ALPHA)-BOC-L-GLUTAMINE
  • N-ALPHA-TERT-BUTYLOXYCARBONYL-L-GLUTAMINE
  • NALPHA-(TERT-BUTOXYCARBONYL)-L-GLUTAMINE
  • N-ALPHA-T-BOC-L-GLUTAMINE
  • N-ALPHA-T-BUTOXYCARBONYL-L-GLUTAMINE
  • N-(TERT-BUTOXYCARBONYL)-L-GLUTAMINE
  • N-T-BOC-L-GLUTAMINE
  • N-T-BUTOXYCARBONYL-L-GLUTAMINE
  • N<SUB>α</SUB>-(tert-Butoxycarbonyl)-L-glutamine
  • -alpha-t-BOC-L-glutamine
  • N-α-Boc-L-glutamine
  • N(a)-Boc-L-glutamine
  • NA-T-BOC-L-GLUTAMINE
  • N-TERT-BUTOXYCARBONYLGLUTAMINE
  • Nalpha-BOC-L-Glutamine, 99+%
  • n(à)-boc-l-glutamine
  • n(à)-tert-butoxycarbonyl-l-glutamine
  • N-ALPHA-T-BUTYLOXYCARBONYL-L-GLUTAMINE
  • N2-[(tert-butoxy)carbonyl]-L-glutamine
  • Boc-Gln-OH 98%
  • L-GLUTAMINE-N-T-BOC (ALPHA-15N+)
  • Boc-L-glutamine≥ 98% (HPLC)
  • (S)-2-[(tert-Butoxycarbonyl)aMino]-4-carbaMoylbutanoic Acid
  • N2-Carboxy-glutaMine N-tert-Butyl Ester
  • NSC 334370
  • Nalpha-Boc-L-glutamine Boc-Gln-OH
  • (Tert-Butoxy)Carbonyl Gln-OH
  • n-(tert-butoxycarbonyl)-l-glutamine CAS NO.13726-85-7
  • Nα-(tert-Butoxycarbonyl)-L-glutamine &gt
  • N-(tert-Butoxycarbonyl)-L-glutamine USP/EP/BP