108392-01-4

Usage

Uses

Used in Organic Synthesis:
TRIMETHYLSILYL-L(+)RHAMNOSE is used as a building block for the synthesis of complex organic molecules. Its trimethylsilyl group provides stability and facilitates selective reactions at other functional groups, making it a valuable component in the construction of intricate molecular structures.
Used in Pharmaceutical Compound Preparation:
TRIMETHYLSILYL-L(+)RHAMNOSE is used as a key intermediate in the preparation of pharmaceutical compounds. Its protective group function allows for the selective modification of the rhamnose molecule, enabling the development of novel and effective drug candidates.
Used in Natural Product Synthesis:
TRIMETHYLSILYL-L(+)RHAMNOSE is employed as a starting material in the synthesis of natural products. Its unique properties and reactivity make it suitable for the construction of complex natural product structures, contributing to the discovery of new bioactive compounds with potential therapeutic applications.
Used in Protective Group Chemistry:
TRIMETHYLSILYL-L(+)RHAMNOSE is used as a protective group for the hydroxyl group of rhamnose in organic reactions. This allows chemists to selectively modify other functional groups in the molecule without affecting the hydroxyl group, providing greater control over the reaction outcomes and facilitating the synthesis of desired products.

Upstream product

• 1246030-28-3 3α,11α,30-trihydroxylup-20(29)-en-23,28-dioic acid 28-O-[α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl]ester 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 1246030-30-7 3α,19β,O-dihydroxylupane-23,28-dioic acid 28-O-[α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl]ester 
• 75-77-4 chloro-trimethyl-silane 
• 73-34-7 L-rhamnose 
• 21149-38-2 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide 
• 3615-41-6 L-Rhamnose 
• 88434-24-6 marthasteroside A₂ 
• 2280-44-6 D-Glucose 
• 73-34-7 D-Fucose 
• 1307292-22-3 (25R)-26-O-β-D-glucopyranosyl-furosta-5,20(22)-diene-1β,3β,26-triol 1-O-[α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside] 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 1268813-04-2 mirabamide F 

Relevant academic research and scientific papers

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.

Trifasciatosides A-J, steroidal saponins from Sansevieria trifasciata

Four previously unreported steroidal saponins, trifasciatosides A-D (1-4), three pairs of previously undescribed steroidal saponins, trifasciatosides E-J (5a, b-7a, b) including acetylated ones, together with twelve known compounds were isolated from the n-butanol soluble fraction of the methanol extract of Sansevieria trifasciata. Their structures were elucidated on the basis of detailed spectroscopic analysis, including 1H-NMR, 13C-NMR, 1H-1H correlated spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC), total correlated spectroscopy (TOCSY), nuclear Overhauser enhancement and exchange spectroscopy (NOESY), electrospray ionization-time of flight (ESI-TOF)-MS and chemical methods. Compounds 2, 4, and 7a, b exhibited moderate antiproliferative activity against HeLa cells.

Cytotoxic protobassic acid glycosides from Planchonella obovata leaf

Four triterpenoid glycosides, possessing protobassic acid as common aglycon, together with 16 known compounds were isolated from the leaves of Planchonella obovata. They are 6β-hydroxy-conyzasaponin G (2), 3?-O-de-β-D-apiofuranosylisoarganin F (3), isoarganin F (4), and 6β-hydroxy-conyzasaponin N (5). The structures of these glycosides were elucidated based on spectroscopic analysis, in particular using 1D TOCSY to con.rm the 1H NMR assignment of each sugar residue. The absolute con.guration of each monosaccharide in the glycon part was determined by GC-FID. Compound 5, Mi-saponin A (8), and ursolic acid (10) showed moderate inhibitory activities against HL-60 leukemia cell line with the IC50 values of 16.88, 15.50, and 12.68 μM, respectively.

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.

Furostanol saponins from the seeds of Allium cepa L.

Allium cepa L. is one of the most widely cultivated and used plants. In addition to its bulb (onion), which is used as food in many cultures, the seeds of A. cepa L. are used as a traditional herbal medicine by the Uygur nationality in China to treat diarrhea and promote blood flow. In a bioactivity-screening, the ethanol extract of seeds of A. cepa L. showed inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) enzyme, with 81.1% inhibition. Phytochemical investigation of the ethanol extract of red onion (Allium cepa L.) seeds led to the isolation of eight new furostanol saponins, named ceparosides E-L (1-8). Their structures were established using 1D and 2D NMR spectroscopy, mass spectrometry and chemical methods. Compounds 1-8 were screened for inhibitory effects on the PTP1B enzyme and cytotoxic activity against five human cells, including HCT-8, Bel-7402, BGC-823, A549 and A2780, but all were found to be inactive.

A new triterpenoid saponin from Gynostemma pentaphyllum

A new dammarane-type triterpene saponin was isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino. Its structural elucidation was accomplished mainly on the basis of the interpretation of spectroscopic data, such as IR, HR-TOF-MS and NMR. Its cytotoxic activity was evaluated against one human cancer cell line HL-60 using MTT assay.

Mirabamides E-H, HIV-inhibitory depsipeptides from the sponge Stelletta clavosa

Four new depsipeptides, mirabamides E-H (1-4), and the known depsipeptide mirabamide C (5) have been isolated from the sponge Stelletta clavosa, collected from the Torres Strait. The planar structures were determined on the basis of extensive 1D and 2D NMR and HRESIMS. The absolute configurations were established by the advanced Marfey's method, NMR, and GC-MS. The four new compounds all showed strong inhibition of HIV-1 in a neutralization assay with IC50 values of 121, 62, 68, and 41 nM, respectively.

A new ursane-type triterpenoid glycoside from Centella asiatica leaves modulates the production of nitric oxide and secretion of TNF-α in activated RAW 264.7 cells

One new ursane-type triterpenoid glycoside, asiaticoside G (1), five triterpenoids, asiaticoside (2), asiaticoside F (3), asiatic acid (4), quadranoside IV (5), and 2α,3β,6β-trihydroxyolean-12-en-28-oic acid 28-O-[α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl- (1→6)-β-d-glucopyranosyl] ester (6), and four flavonoids, kaempferol (7), quercetin (8), astragalin (9), and isoquercetin (10) were isolated from the leaves of Centella asiatica. Their chemical structures were elucidated by mass, 1D- and 2D-nuclear magnetic resonance (NMR) spectroscopy. The structure of new compound 1 was determined to be 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. The anti-inflammatory activities of the isolated compounds were investigated on lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Asiaticoside G (1) potently inhibited the production of nitric oxide and tumor necrosis factor-α with inhibition rates of 77.3% and 69.0%, respectively, at the concentration of 100 μM.

2-Acety-1-(3-glycosyloxyoctadecanoyl)glycerol and dammarane triterpenes in the exudates from glandular trichome-like secretory organs on the stipules and leaves of Cerasus yedoensis

A glycolipid, 2-acetyl-1-{3-[3,4-di-O-acetyl-β-d-glucopyranosyl-(1 → 3)-2-O-acetyl-α-l-rhamnopyranosyloxy]octadecanoyl}-sn-glycerol (1) and a dammarane triterpene, (2α,20S)-2,20-dihydroxydammar-24-en-3-one (2), along with known (20S)-20-hydroxydammar-24-en-3-one (3), were isolated from the exudates of the glandular trichome-like secretory organs in the young stipules and leaves of Cerasus yedoensis (Rosaceae).