108392-01-4

Basic information

• Product Name: TRIMETHYLSILYL-L(+)RHAMNOSE
• Synonyms: TRIMETHYLSILYL-L(+)RHAMNOSE;trimethylsilyl-L-plus-rhamnose*mixed anomers
• CAS NO: 108392-01-4
• Molecular Formula: C₁₈H₄₄O₅Si₄
• Molecular Weight: 236.34
• Product Categories: Carbohydrates;Carbohydrates A to;Carbohydrates P-ZBiochemicals and Reagents;Monosaccharide
• Mol File: 108392-01-4.mol
• Article Data: 16

Chemical Properties

• Appearance: clear, colorless/liquid
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TRIMETHYLSILYL-L(+)RHAMNOSE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLSILYL-L(+)RHAMNOSE(108392-01-4)
• EPA Substance Registry System: TRIMETHYLSILYL-L(+)RHAMNOSE(108392-01-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 108392-01-4(Hazardous Substances Data)

Usage

General Description

TRIMETHYLSILYL-L(+)RHAMNOSE is a chemical compound that is commonly used in organic synthesis and as a building block for the preparation of complex molecules. It is a derivative of L(+)rhamnose, a naturally occurring sugar molecule found in plants. The trimethylsilyl group attached to the rhamnose molecule makes it more stable and easier to handle in organic reactions. This chemical is often used as a protective group for the hydroxyl group of rhamnose, allowing for selective reactions to occur at other functional groups in the molecule. It is also used in the preparation of natural products and pharmaceutical compounds.

Upstream product

• 6014-42-2 L-rhamnose 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 75-77-4 chloro-trimethyl-silane 
• 73-34-7 L-rhamnose 
• 21149-38-2 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide 
• 88434-24-6 marthasteroside A₂ 
• 2280-44-6 D-Glucose 
• 73-34-7 D-Fucose 
• 1268813-04-2 mirabamide F 
• 1268813-03-1 mirabamide E 
• 1300063-95-9 2α,3β,23,30-tetrahydroxyurs-12-en-28-oic acid 28-O-[α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl] ester 

Relevant articles and documents

New steroidal saponins from the roots of Solanum melongena L.

Phytochemical investigation of the roots of Solanum melongena L. resulted in the isolation of six new steroidal saponins, including five new cholestane saponins (1-5) and one new steroidal alkaloid (6), along with one new natural product (7) and three know steroids (8-10). The structures of all isolated compounds were determined by 1D and 2D NMR experiments and by comparison of their spectroscopic and physical data with literature values. The inhibitory activities on nitric oxide (NO) production stimulated by lipopolysaccharide (LPS) in a RAW 264.7 cell line were assayed for all the isolated compounds. Compounds 1, 2 and 4–9 exhibited moderate inhibition of NO production with IC50 values ranging from 12.6 to 59.5 μM.

An efficient method for the preparation of 1,5-anhydroalditol from unprotected carbohydrates via glycopyranosyl iodide

A practical, facile method was developed for the preparation of 1,5-anhydroalditol via per-O-TMS-glycopyranosyl iodide with LiBH4. A series of 1,5-anhydroalditols were prepared in excellent yields (up to 92%) from unprotected carbohydrates within 2 days under mild conditions. In addition, multi-gram scale preparation of 1,5-anhydroglucitol (1,5-AG), a major polyol present in human serum, was developed using the same procedure without the need for chromatographic purification.

Microwave-assisted one-pot synthesis of 1,6-anhydrosugars and orthogonally protected thioglycosides

Living organisms employ glycans as recognition elements because of their large structural information density. Well-defined sugar structures are needed to fully understand and take advantage of glycan functions, but sufficient quantities of these compounds cannot be readily obtained from natural sources and have to be synthesized. Among the bottlenecks in the chemical synthesis of complex glycans is the preparation of suitably protected monosaccharide building blocks. Thus, easy, rapid, and efficient methods for building-block acquisition are desirable. Herein, we describe routes directly starting from the free sugars toward notable monosaccharide derivatives through microwave-assisted one-pot synthesis. The procedure followed the in situ generation of per-O-trimethylsilylated monosaccharide intermediates, which provided 1,6-anhydrosugars or thioglycosides upon treatment with either trimethylsilyl trifluoromethanesulfonate or trimethyl(4-methylphenylthio)silane and ZnI2, respectively, under microwave irradiation. We successfully extended the methodology to regioselective protecting group installation and manipulation toward a number of thioglucosides and the glycosylation of persilylated derivatives, all of which were conducted in a single vessel. These developed approaches open the possibility for generating arrays of suitably protected building blocks for oligosaccharide assembly in a short period with minimal number of purification stages.