79999-47-6

Usage

Uses

Used in Organic Synthesis:
TRI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL is used as a protective agent for alcohols, allowing for selective functionalization of the compound in various chemical reactions.
Used in Pharmaceutical Industry:
TRI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL is used as a precursor in the synthesis of complex organic molecules, particularly in the preparation of natural products and pharmaceuticals. Its protective TBDMS groups facilitate the selective functionalization required for creating specific drug molecules.
Used in Synthesis of Natural Products:
TRI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL is utilized as a key intermediate in the synthesis of natural products, where its protected hydroxyl groups enable the construction of intricate molecular structures with precision.

InChI:InChI=1/C24H52O4Si3/c1-22(2,3)29(10,11)26-18-20-21(28-31(14,15)24(7,8)9)19(16-17-25-20)27-30(12,13)23(4,5)6/h16-17,19-21H,18H2,1-15H3/t19-,20-,21+/m1/s1

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 13265-84-4 D-glucal 
• 2873-29-2 D-glucal triacetate 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 105938-06-5 ((4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-trimethyl-silane 
• 105938-02-1 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol 
• 100924-13-8 (1S,3R,4R,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-8-(toluene-4-sulfonyl)-2-oxa-8-aza-bicyclo[4.2.0]octan-7-one 
• 1323988-36-8 (1S)-1,5-anhydro-2-deoxy-1-(2,6-dimethoxyphenyl)-3,4,6-tris-O-(tert-butyldimethylsilyl)-D-erythro-hex-2-enitol 
• 1621188-34-8 methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-tert-butyldimethylsilyl-2-deoxy-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside 
• 1621188-35-9 methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-tert-butyldimethylsilyl-2-deoxy-β-D-erythro-hexapyranosyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Electrochemical Trifluoromethylation of Glycals

Carbohydrates play essential roles in various physiological and pathological processes. Trifluoromethylated compounds have wide applications in the field of medicinal chemistry. Herein, we report a practical and efficient trifluoromethylation of glycals b

Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals

A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.

Method for preparing 3,4,6-tri-O-substituent-D-glucal

The invention discloses a method for preparing 3,4,6-tri-O-substituent-D-glucal. The method comprises the following steps: (1) preparation of D-glucal: subjecting 3,4,6-tri-O-acetyl-D-glucal, which serves as a starting raw material, to a reaction under al

Convergent One-Pot Oxidative [n + 1] Approaches to Spiroacetal Synthesis

Two one-pot oxidative annulative approaches to spiroacetal synthesis are described. One approach uses a Lewis acid mediated Ferrier reaction in the fragment-coupling stage followed by DDQ-promoted oxidative carbon-hydrogen bond cleavage and cyclization. An alternative approach employs a Heck reaction for fragment coupling followed by DDQ-mediated enone formation and cyclization. These strategies provide convergent routes to common subunits in natural products, medicinal agents, and chemical libraries under mild reaction conditions.

A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.

Oxidant-controlled heck-type C-glycosylation of glycals with arylboronic acids: Stereoselective synthesis of aryl 2-deoxy-C-glycosides

Oxidative Heck-type C-glycosylations of glycals with various arylboronic acids using Pd(OAc)2 as catalyst in the presence of oxidant were developed. The corresponding ketone, enol ether, and enone types of C-glycosides were predictably obtained

Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides

The Heck coupling of aryl iodides with pyranoid glycals using a catalytic amount of Pd(OAc)2 to form pyranoid aryl C-glycosides has been achieved. The reaction takes place smoothly in the presence of Ag 2CO3 and Cu(OAc)2 (or DMSO) in acetonitrile. This arylation process, which occurs in a highly regio- and stereo-selective manner, provides a simple, mild, and efficient approach to the synthesis of aryl 2-deoxy-C-glycopyranosides.

Tandem epoxidation-alcoholysis or epoxidation-hydrolysis of glycals catalyzed by titanium(IV) isopropoxide or Venturello's phosphotungstate complex

Venturello's phosphotungstate complex and titanium(IV) isopropoxide [Ti(O-i-Pr)4] were successfully used as catalysts for the epoxidation-alcoholysis of glycals using hydrogen peroxide [H2O 2]. Reaction substrates included a range of variously protected glycals and different alcohols were used as solvents. Ti(O-i-Pr)4 was only effective in methanol as solvent, but gave methyl glycosides in high yields and high selectivities. The Venturello complex proved to be a very versatile and efficient catalyst. Apart from epoxidation-alcoholysis in alcoholic solvents it also showed activity in biphasic conditions to allow for glycosylation of long-chain alcohols and was very effective in the stereoselective dihydroxylation of benzylated glucal.

Synthesis of novel migrastatin and dorrigocin A analogues from D-glucal

The synthesis of a range of analogues of the migrastatin macrolide core has been achieved from tri-O-acetyl-D-glucal in order to facilitate structure-activity studies. Efficient macrolactone formation was achieved in the presence of a reactive olefin, by

The synthesis of a new class of potential inhibitors for glycoside hydrolases

Some attempts toward the synthesis of novel inhibitors of glycosyl transferases are described. More successfully, the synthesis of an activated cyclopropacyclohexene and an amide and an amine of a cyclopropa-fused pyranose are described. None of these three novel compounds proved to be a significant inhibitor of a retaining α-glucosidase from barley. Copyright Taylor & Francis, Inc.