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Merck
CN
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文件

670359

Sigma-Aldrich

乙酰基硫甲基-硼烷二苯基膦复合物

≥98.0%

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别名:
(T-4)-[S-[(Diphenylphosphino-κP)methyl] ethanethioate]trihydroboron
经验公式（希尔记法）:
C15H18BOPS
CAS号:
446822-71-5
分子量:
288.15
UNSPSC代码:
12352200
PubChem化学物质编号:
329760266
NACRES:
NA.22

检测方案

≥98.0%

形式

solid

反应适用性

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

mp

52-55 °C

官能团

phosphine

储存温度

2-8°C

SMILES字符串

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 key

MXPNVFCCEGQGEN-UHFFFAOYSA-N

应用

  • 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.
  • After reaction with an azide, the phosphine is eliminated in the presence of water to yield a native amide bond.
  • Used in the synthesis of cyclic peptides.
Acetylthiomethyl-diphenylphosphine borane complex Ligation with DABCO

包装

Bottomless glass bottle. Contents are inside inserted fused cone.

法律信息

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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说明
价格

象形图

Exclamation mark
GHS07

警示用语：

Warning

危险声明

H315,H319,H335

危险分类

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

靶器官

Respiratory system

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

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

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Raines Group – Professor Product Portal

Professor Ron Raines works with Sigma-Aldrich on the development of reagents and tools for chemical biology such as the traceless Staudinger ligation reagent (670359). DTBA (774405), a superior biological reducing reagent to DTT, is another technology to come out of the Raines lab.

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