1769-00-2

Basic information

• Product Name: per-O-trimethylsilyl-D-galactopyranoside
• CAS NO: 1769-00-2
• Molecular Weight: 541.068
• Mol File: 1769-00-2.mol
• Article Data: 67

Chemical Properties

• CAS DataBase Reference: per-O-trimethylsilyl-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: per-O-trimethylsilyl-D-galactopyranoside(1769-00-2)
• EPA Substance Registry System: per-O-trimethylsilyl-D-galactopyranoside(1769-00-2)

Safety Data

• Hazardous Substances Data: 1769-00-2(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 59-23-4 D-Galactose 
• 10257-28-0 D-Galactose 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2754-27-0 trimethylsilyl acetate 
• 2280-44-6 D-Glucose 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 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 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 

Downstream Products

• 1541195-51-0 (2S,3S,4R)-2-azido-3,4-O-dibenzyl-1-O-α-D-galactopyranosyloctadec-6-ene-1,3,4-triol 
• 1541195-95-2 C₅₀H₈₉N₃O₈Si₄ 
• 1613320-91-4 (2S,3S,4R)-3,4-O-dibenzyl-1-O-α-D-galactopyranosyl-2-hexacosanoylaminooctadec-6-ene-1,3,4-triol 
• 1193338-16-7 terricollene A 

Relevant articles and documents

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.

A practical and scalable synthesis of KRN7000 using glycosyl iodide as the glycosyl donor

KRN7000 is particularly useful because it is a powerful and specific CD1d agonist and has prompted intense interest in the context of immunology in the past 25 years. Its limited commercial availability and high price has led to the publication of many different syntheses. However, almost all of them focused on the methodology development rather than a scalable synthesis. Herein, we have described a practical and scalable procedure for the synthesis of KRN7000 basing on the glycosyl iodide method. This procedure involves total of eight steps to obtain the highly pure product KNR7000 on gram scale from the commercially available starting materials (d-galactose and the phytosphingosine) with only three column chromatographic purifications.

Cholesteryl glucosides signal through the carbohydrate recognition domain of the macrophage inducible C-type lectin (mincle)

Cholesteryl α-d-glucosides (αGCs) are unique metabolic products of the cancer-causing human pathogenHelicobacter pylori.Viasignalling through the Macrophage inducible C-type lectin (Mincle) and the induction of a pro-inflammatory response, they are thought to play a role in the development of gastric atrophy. Herein, we prepared the first library of steryld-glucosides and determined that they preferentially signal through the carbohydrate recognition domain of human Mincle, rather than the amino acid consensus motif. Lipidated steryld-glucosides exhibited enhanced Mincle agonist activity, with C18 cholesteryl 6-O-acyl-α-d-glucoside (2c) being the most potent activator of human monocytes. Despite exhibiting strong Mincle signalling, sito- (5b) and stigmasterol glycosides (6b) led to a poor inflammatory response in primary cells, suggesting that Mincle is a potential therapeutic target for preventingH. pylori-mediated inflammation and cancer.