18623-26-2

Basic information

• Product Name: TRIMETHYLSILYL-L-(+)-ARABINOSE
• Synonyms: TRIMETHYLSILYL-L-(+)-ARABINOSE;TMS-Arabinose;2-O,3-O,4-O,5-O-Tetrakis(trimethylsilyl)-L-arabinose
• CAS NO: 18623-26-2
• Molecular Formula: C8H18O5Si
• Molecular Weight: 222.31102
• Mol File: 18623-26-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TRIMETHYLSILYL-L-(+)-ARABINOSE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLSILYL-L-(+)-ARABINOSE(18623-26-2)
• EPA Substance Registry System: TRIMETHYLSILYL-L-(+)-ARABINOSE(18623-26-2)

Safety Data

• Hazardous Substances Data: 18623-26-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
TRIMETHYLSILYL-L-(+)-ARABINOSE is used as a protecting group for the hydroxyl group in arabinose, facilitating selective reactions at other functional groups on the sugar molecule. This selective protection is crucial for the synthesis of complex organic compounds where precise control over the reaction sites is necessary.
Used in Pharmaceutical Development:
TRIMETHYLSILYL-L-(+)-ARABINOSE is used as a versatile building block in the development of various pharmaceuticals. Its role in the synthesis of nucleoside analogs and other bioactive molecules highlights its importance in creating new and effective drugs.
Used in the Preparation of Nucleoside Analogs:
TRIMETHYLSILYL-L-(+)-ARABINOSE is used as a key component in the preparation of nucleoside analogs, which are essential in the development of antiviral and anticancer medications. TRIMETHYLSILYL-L-(+)-ARABINOSE's ability to protect the hydroxyl group during synthesis contributes to the successful creation of these therapeutic agents.
Used in Bioactive Molecule Synthesis:
TRIMETHYLSILYL-L-(+)-ARABINOSE is used as a fundamental building block in the synthesis of bioactive molecules, which have potential applications in medicine, agriculture, and other fields. Its versatility in organic chemistry allows for the creation of a wide range of biologically active compounds with diverse functions and properties.

Synthetic route

chloro-trimethyl-silane (75-77-4) + (23S)-21R-O-n-butyl-19-oxo-3β,20ξ,21-trihydroxy-21,23-epoxydammar-24-ene 3-O-[α-L-rhamnopyranosyl(1->2)][β-D-xylopyranosyl(1->3)]-α-L-arabinopyranoside → C19H44O5Si3 + C17H42O5Si4 (18623-26-2) + 2,3,4,5-Tetra-O-trimethylsilylxylose (18623-22-8)

Conditions	Yield
Stage #1: (23S)-21R-O-n-butyl-19-oxo-3β,20ξ,21-trihydroxy-21,23-epoxydammar-24-ene 3-O-[α-L-rhamnopyranosyl(1->2)][β-D-xylopyranosyl(1->3)]-α-L-arabinopyranoside With hydrogenchloride; water In methanol at 90℃; for 6h; Stage #2: chloro-trimethyl-silane With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane at 20℃; for 0.25h;

chloro-trimethyl-silane (75-77-4) + (23S)-21S-O-n-butyl-19-oxo-3β,20ξ,21-trihydroxy-21,23-epoxydammar-24-ene 3-O-[α-L-rhamnopyranosyl(1->2)][β-D-xylopyranosyl(1->3)]-α-L-arabinopyranoside → C19H44O5Si3 + C17H42O5Si4 (18623-26-2) + 2,3,4,5-Tetra-O-trimethylsilylxylose (18623-22-8)

Conditions	Yield
Stage #1: (23S)-21S-O-n-butyl-19-oxo-3β,20ξ,21-trihydroxy-21,23-epoxydammar-24-ene 3-O-[α-L-rhamnopyranosyl(1->2)][β-D-xylopyranosyl(1->3)]-α-L-arabinopyranoside With hydrogenchloride; water In methanol at 90℃; for 6h; Stage #2: chloro-trimethyl-silane With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane at 20℃; for 0.25h;

Upstream product

• 75-77-4 chloro-trimethyl-silane 

Relevant articles and documents

Triterpenoid saponins from Gynostemma pentaphyllum

Four new dammarane-type triterpene saponins, 1-4, were isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino. Their structural elucidations were accomplished mainly on the basis of spectroscopic methods, such as IR, HR-TOF-MS, and NMR. Compounds 1-4 showed moderate cytotoxic activities against cancer cell lines HL-60, Colon205, and Du145 in vitro.