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 
• 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 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 1015696-25-9 (25R)-26-O-β-D-glucopyranosyl-22α-methoxy-5α-furostan-3β,26-diol 3-O-β-D-glucopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside 
• 492-61-5 β-D-glucose 
• 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 
• 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 

Downstream Products

• 352432-46-3 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranosyl iodide 

Relevant articles and documents

Selective Acetylation of Non-anomeric Groups of per- O-Trimethylsilylated Sugars

Selective modification of the hydroxyl groups of sugars has been a long-standing challenge due to their proximate relative reactivity. Herein, we report a TMSOTf-catalyzed selective acetylation of the non-anomeric hydroxyl groups of several per-O-TMS-protected sugar substrates while leaving their anomeric group unaffected. In addition to standing versatile by itself, the anomeric O-TMS group left intact can be functionalized to afford key sugar precursors such as imidate donors, which could otherwise be synthesized via a stepwise anomeric deprotection-functionalization procedure.

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 palladium-catalyzed approach to allenic aromatic ethers and first total synthesis of terricollene A

A palladium-catalyzed C-O bond formation reaction between phenols and allenylic carbonates to give 2,3-allenic aromatic ethers with decent to excellent yields under mild reaction conditions has been described. A variety of synthetically useful functional