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重要文件

670359

Sigma-Aldrich

乙酰基硫甲基-硼烷二苯基膦复合物

≥98.0%

同義詞:

(T-4)-[S-[(Diphenylphosphino-κP)methyl] ethanethioate]trihydroboron

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About This Item

經驗公式(希爾表示法):
C15H18BOPS
CAS號碼:
分子量::
288.15
分類程式碼代碼:
12352200
PubChem物質ID:
NACRES:
NA.22
暫時無法取得訂價和供貨情況

化驗

≥98.0%

形狀

solid

反應適用性

reaction type: click chemistry
reagent type: ligand
reaction type: Staudinger Reaction

mp

52-55 °C

官能基

phosphine

儲存溫度

2-8°C

SMILES 字串

B.CC(=O)SCP(c1ccccc1)c2ccccc2

InChI

1S/C15H15OPS.BH3/c1-13(16)18-12-17(14-8-4-2-5-9-14)15-10-6-3-7-11-15;/h2-11H,12H2,1H3;1H3

InChI 密鑰

MXPNVFCCEGQGEN-UHFFFAOYSA-N

應用

  • Traceless Staudinger ligation reagent with borane protecting group.
  • The borane group stabilizes the phosphine against oxidation and can be easily removed with mild basic or acidic conditions to yield the active phosphine.[1]
  • After reaction with an azide, the phosphine is eliminated in the presence of water to yield a native amide bond.[2]
  • Used in the synthesis of cyclic peptides.[2]
Acetylthiomethyl-diphenylphosphine borane complex Ligation with DABCO

包裝

Bottomless glass bottle. Contents are inside inserted fused cone.

法律資訊

授权后方可销售,仅供研发使用。美国专利 6,974,884 和相关专利申请

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訊號詞

Warning

危險聲明

危險分類

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

標靶器官

Respiratory system

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

dust mask type N95 (US), Eyeshields, Gloves


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Matthew B Soellner et al.
The Journal of organic chemistry, 67(14), 4993-4996 (2002-07-06)
The Staudinger ligation of peptides with a C-terminal phosphinothioester and N-terminal azide is an emerging method in protein chemistry. Here, the first Staudinger ligations of nonglycyl azides are reported and shown to proceed both in nearly quantitative yield and with
Michaela Mühlberg et al.
Bioorganic & medicinal chemistry, 18(11), 3679-3686 (2010-05-15)
The traceless Staudinger ligation has recently found various applications in the field of peptide synthesis and modification, including immobilization and cyclization strategies. In this report, we utilize the traceless Staudinger ligation in the formation of amide bonds, which allows the

相關內容

Traceless Staudinger Ligation

Raines lab innovations include traceless Staudinger ligation and DTBA reagent, advancing chemical biology research with Sigma-Aldrich.

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