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Boc-4-pinicalborane-L-phenylalanine

Product Name
Boc-4-pinicalborane-L-phenylalanine
CAS No.
216439-76-8
Chemical Name
Boc-4-pinicalborane-L-phenylalanine
Synonyms
216439-76-8;Boc-4-Pinicalborane-L-Phe-OH;Boc-4-pinicalborane-L-phenylalanine;Boc-4-pinacol borate L-phenylalanine;N-Boc-4-(pinacolyloxylboronyl)-L-phenylalanine;N-tert-butyloxycarbonyl-4-pinacolatoborono-L-phenylalanine;N-Boc-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-phenylalanine;N-[(1,1-Dimethylethoxy)carbonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-phenylalanine;L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid
CBNumber
CB72684308
Molecular Formula
C20H30BNO6
Formula Weight
391.27
MOL File
216439-76-8.mol
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Boc-4-pinicalborane-L-phenylalanine Property

Boiling point:
537.2±50.0 °C(Predicted)
Density 
1.14±0.1 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
pka
3.86±0.10(Predicted)
Appearance
White to off-white Solid
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Synthonix
Product number
B22364
Product name
(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoicacid
Purity
97%
Packaging
100mg
Price
$60
Updated
2021/12/16
ChemScene
Product number
CS-M3317
Product name
L-Phenylalanine,N-[(1,1-dimethylethoxy)carbonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
Packaging
250mg
Price
$61
Updated
2021/12/16
Synthonix
Product number
B22364
Product name
(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoicacid
Purity
97%
Packaging
250mg
Price
$80
Updated
2021/12/16
Activate Scientific
Product number
AS102295
Product name
N-Boc-4-(pinacolyloxylboronyl)-L-phenylalanine
Purity
95% ee
Packaging
250mg
Price
$95
Updated
2021/12/16
ChemScene
Product number
CS-M3317
Product name
L-Phenylalanine,N-[(1,1-dimethylethoxy)carbonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
Packaging
1g
Price
$123
Updated
2021/12/16
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Boc-4-pinicalborane-L-phenylalanine Chemical Properties,Usage,Production

Synthesis

220587-29-1

216439-76-8

119771-23-2

Synthesis of (S)-2-((tert-butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propionic acid from methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propionate and ( S)-3-(4-boronic acid phenyl)-2-((tert-butoxycarbonyl)amino)propionic acid was performed in the following general steps: the above organic ester layer was stirred with an aqueous lithium hydroxide solution (23 g, dissolved in 500 mL of water) for 30 min at room temperature. The pH of the reaction mixture was adjusted to about 10 with 6N hydrochloric acid and subsequently filtered. The filter cake was washed with 200 mL of water. Acetonitrile was removed from the filtrate by distillation under reduced pressure to give an aqueous slurry (water was supplemented during distillation to a total volume of 950 mL). The slurry was filtered through a 20 micron cellulose pad and the filter cake was washed with 200 mL of water. The filtrate was washed with 500 mL of methyl tertiary butyl ether (MTBE) and then rediluted with 700 mL of MTBE. The mixture was acidified with 6N hydrochloric acid to pH about 4.5. The organic layer was washed with 500 mL of water and concentrated under reduced pressure to give the target acid compound as a brown oil (206 g, estimated purity of 95% based on NMR). The crude product can be used directly in the next step of the reaction. Alternatively, it can be purified by solvent recrystallization from MTBE/heptane mixture to give a white solid product containing a small amount of (S)-3-(4-boronic acid phenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid. Mass spectral (ESI) data: MH+ = 392.2, MNH4+ = 409.2, M2H+ = 783.4, M2NH4+ = 800.4. 1H NMR (CDCl3) δ 7.95 (br s, 1H), 7.76 (d, J = 7.8 Hz, 2H), 7.21 (d, J = 7.6 Hz, 2H), 5.03 (d, J = 7.8 Hz, 1H), 4.62 (m, 1H), 3.18 (m, 2H), 1.43 (s, 9H), 1.35 (s, 12H).13C NMR (CDCl3) δ 175.8, 155.7, 139.7, 135.4, 129.2, 84.2, 80.5, 54.5, 38.3, 28.7, 25.2.

References

[1] Patent: US2009/62540, 2009, A1. Location in patent: Page/Page column 8-9
[2] Patent: US2009/88447, 2009, A1. Location in patent: Page/Page column 5-6

Boc-4-pinicalborane-L-phenylalanine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Boc-4-pinicalborane-L-phenylalanine manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD
Product
(S)-2-((tert-Butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid 216439-76-8
Price
US $2.00-5.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2025-06-24
Career Henan Chemical Co
Product
Boc-4-pinicalborane-L-phenylalanine 216439-76-8
Price
US $6.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1kg, 5kg, 50kg
Release date
2020-01-09

216439-76-8, Boc-4-pinicalborane-L-phenylalanineRelated Search:


  • Boc-4-pinicalborane-L-phenylalanine
  • (S)-2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid
  • L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
  • N-Boc-4-(pinacolyloxylboronyl)-L-phenylalanine
  • 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid
  • N-tert-butyloxycarbonyl-4-pinacolatoborono-L-phenylalanine
  • N-[(1,1-Dimethylethoxy)carbonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-phenylalanine
  • 216439-76-8
  • N-Boc-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-L-phenylalanine
  • Boc-4-Pinicalborane-L-Phe-OH
  • Boc-4-pinacol borate L-phenylalanine
  • (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoic acid
  • (S)-2-((tert-Butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid - [B22364]
  • 216439-76-8
  • C20H30BNO6