55529-69-6

Basic information

• Product Name: TRIMETHYLSILYL-D(+)MANNOSE
• Synonyms: TRIMETHYLSILYL-D(+)MANNOSE;1,2,3,4,6-Pentakis-O-(trimethylsilyl)-D-mannopyranose;1,2,3,4,6-Penta-O-trimethylsilyl-D-mannopyranoside;1-O,2-O,3-O,4-O,6-O-Pentakis(trimethylsilyl)-D-mannopyranose;1,2,3,4,6-Penta-O-trimethylsilyl-D-mannopyranose
• CAS NO: 55529-69-6
• Molecular Formula: C₂₁H₅₂O₆Si₅
• Molecular Weight: 252.337
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 55529-69-6.mol
• Article Data: 67

Chemical Properties

• Appearance: /
• Refractive Index: 1.443
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: TRIMETHYLSILYL-D(+)MANNOSE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLSILYL-D(+)MANNOSE(55529-69-6)
• EPA Substance Registry System: TRIMETHYLSILYL-D(+)MANNOSE(55529-69-6)

Safety Data

• Hazardous Substances Data: 55529-69-6(Hazardous Substances Data)

Usage

Description

TRIMETHYLSILYL-D(+)MANNOSE, also known as 1,2,3,4,6-Penta-O-trimethylsilyl-D-mannopyranoside (CAS# 55529-69-6), is a colorless liquid compound that is useful in organic synthesis. It is a derivative of D-mannose, a monosaccharide, with five trimethylsilyl groups attached to its hydroxyl groups, which provides unique chemical properties and reactivity for various applications in different industries.

Uses

Used in Organic Synthesis:
TRIMETHYLSILYL-D(+)MANNOSE is used as a synthetic intermediate for the synthesis of various organic compounds. Its unique trimethylsilyl-protected hydroxyl groups make it a versatile building block in the preparation of complex organic molecules, particularly in the fields of pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, TRIMETHYLSILYL-D(+)MANNOSE is used as a key intermediate in the development of novel drug candidates. Its unique chemical properties allow for the creation of new molecules with potential therapeutic applications, contributing to the advancement of drug discovery and development.
Used in Agrochemical Industry:
TRIMETHYLSILYL-D(+)MANNOSE is also utilized in the agrochemical industry for the synthesis of bioactive compounds with potential applications in pest control, crop protection, and other agricultural practices. Its unique structure and reactivity enable the development of innovative products that can address various challenges in agriculture.
Used in Specialty Chemicals Industry:
In the specialty chemicals industry, TRIMETHYLSILYL-D(+)MANNOSE is employed as a starting material for the production of various specialty chemicals, such as surfactants, polymers, and additives. Its unique properties allow for the creation of novel products with specific applications in industries like cosmetics, textiles, and coatings.

InChI:InChI=1/C21H52O6Si5/c1-28(2,3)22-16-17-18(24-29(4,5)6)19(25-30(7,8)9)20(26-31(10,11)12)21(23-17)27-32(13,14)15/h17-21H,16H2,1-15H3/t17?,18-,19+,20-,21+/m1/s1

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 59-23-4 D-Galactose 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 10257-28-0 D-Galactose 
• 3646-73-9 α-D-galactopyranose 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2754-27-0 trimethylsilyl acetate 
• 2280-44-6 D-Glucose 
• 73-34-7 D-Fucose 
• 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 
• 24589-78-4 N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide 
• 1356078-99-3 fusaroside 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 
• 1374792-02-5 (25R)-26-O-β-D-glucopyranosyl-22α-methoxy-5α-furostan-3β,26-diol 3-O-β-D-xylopyranosyl-(1->3)-β-D-glucopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside 

Downstream Products

• 352432-46-3 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranosyl iodide 
• 853055-39-7 (2S,3R,4E)-2-azido-3-O-para-methoxybenzyl-1-O-D-galactopyranosyl-4-octadecene 
• 417717-50-1 8-ethoxycarbonyloctyl 4,6-O-benzylidene-α-D-mannopyranoside 
• 417717-61-4 8-ethoxycarbonyloctyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1(3)-4,6-O-benzylidene)-α-D-mannopyranoside 
• 52443-07-9 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonitrile 
• 1269616-92-3 (2S,3S,4R)-2-azido-3,4-di-(benzoyloxy)-1-(α-D-galactopyranosyloxy)nonane 
• 1269616-93-4 (2S,3S,4R)-2-azido-3,4-di-(benzoyloxy)-1-(α-D-galactopyranosyloxy)dodecane 
• 1269616-94-5 (2S,3S,4R)-2-azido-3,4-di-(benzoyloxy)-1-(α-D-galactopyranosyloxy)pentadecane 
• 1089188-04-4 (2S,3S,4R)-1-O-(6-deoxy-6-phenylaminocarbonylamino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol 
• 898531-99-2 (2S,3S,4R)-1-O-(6-deoxy-6-acetamido-α-D-galactopyranosyl)-2-(N-nervonoylamino)-1,3,4-octadecanetriol 
• 1333481-02-9 (S)-4-(N-(2-(1,2,3,4-tetra-O-trimethylsilyl-α-D-glucopyranosyl)-2-oxoethyl)formamido)-3-(benzyldisulfanyl)pent-3-enyl 2-(6-methoxynaphthalen-2-yl)propanoate 
• 1333481-05-2 (S)-4-(N-(2-(α-D-glucopyranose-6-yl)-2-oxoethyl)formamido)-3-(benzyldisulfanyl)pent-3-enyl 2-(6-methoxynaphthalen-2-yl)propanoate 

Relevant articles and documents

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.

Development of a Novel Method for Trimethylsilylation of Saccharides?

The trimethylsilyl (TMS) group is widely used in carbo?hydrate synthesis, although this protecting group is unstable and its post-synthetic purification challenging. The successful trimethylsilyl?ation of carbohydrates mediated by recyclable and efficient

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.