10548-46-6

Basic information

• Product Name: 1,6-ANHYDRO-2,3,4-TRI-O-BENZYL-BETA-D-GLUCOPYRANOSE
• Synonyms: 1,6-ANHYDRO-2,3,4-TRI-O-BENZYL-B-D-GLUCOPYRANOSE;1,6-ANHYDRO-2,3,4-TRI-O-BENZYL-BETA-D-GLUCOPYRANOSE;1,6-ANHYDRO-2,3,4-TRI-O-BENZYL-BETA-D-GLUCOSE;1,6-Anhydro-2,3,4-tri-o-benyl-b-D-glucopyranose;1,6-ANHYDRO-2,3,4-TRI-O-BENZYL-SS-D-GLUCOPYRANOSE;1,6-Anhydro-2,3,4-tris-O-(phenylMethyl)-β-D-glucopyranose;Tri-O-benzyllevoglucosan;2,3,4-Tri-O-benzyl-1,6-anhydro-beta-D-glucopyranose min. 98%
• CAS NO: 10548-46-6
• Molecular Formula: C₂₇H₂₈O₅
• Molecular Weight: 432.51
• Product Categories: Aromatics;Carbohydrates & Derivatives
• Mol File: 10548-46-6.mol

Chemical Properties

• Melting Point: 81-84°C
• Boiling Point: 555.8 °C at 760 mmHg
• Flash Point: 220.8 °C
• Appearance: /
• Density: 1.22 g/cm³
• Vapor Pressure: 8E-12mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: 1,6-ANHYDRO-2,3,4-TRI-O-BENZYL-BETA-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-ANHYDRO-2,3,4-TRI-O-BENZYL-BETA-D-GLUCOPYRANOSE(10548-46-6)
• EPA Substance Registry System: 1,6-ANHYDRO-2,3,4-TRI-O-BENZYL-BETA-D-GLUCOPYRANOSE(10548-46-6)

Safety Data

• Hazardous Substances Data: 10548-46-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,6-Anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of a diverse array of biologically active molecules, making it a valuable asset in drug discovery and development.
Used in Synthesis of Biologically Active Molecules:
1,6-Anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose is used as a synthon for the preparation of biologically important products such as rifamycin S, indanomycin, thromboxane B2, (+)-biotin, tetrodotoxin, quinone, and macrolide antibiotics. Its structural versatility enables the development of novel compounds with potential applications in various therapeutic areas.
Used in Modified Sugars:
1,6-Anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose is also used in the synthesis of modified sugars, which have applications in the development of new drugs and the modification of existing ones to improve their properties, such as solubility, stability, and bioavailability.

InChI:InChI=1/C27H28O5/c1-4-10-20(11-5-1)16-28-24-23-19-31-27(32-23)26(30-18-22-14-8-3-9-15-22)25(24)29-17-21-12-6-2-7-13-21/h1-15,23-27H,16-19H2/t23-,24-,25+,26-,27-/m1/s1

Upstream product

• 78153-79-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride 
• 108800-82-4 ethyl 2,3,5-tri-O-acetyl-1-thio-α/β-D-ribofuranoside 
• 39483-51-7 ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 1037310-33-0 1,4-bis(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)benzene 
• 108-93-0 cyclohexanol 
• 47727-93-5 2,3,4-tri-O-benzyl-D-glucopyranose 
• 107-18-6 allyl alcohol 
• 1079963-29-3 2,3,4-tri-O-benzyl-6-hydroxyl-1-O-propynyl-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 13242-55-2 2,3,4-tri-O-acetyllevoglucosan 
• 479252-05-6 ((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol 
• 762287-68-3 p-tolyl-2,3,4-tri-O-benzyl-6-O-trityl-1-thio-β-D-glucopyranoside 
• 819814-42-1 β-1-p-tolylthio-6-O-trityl-D-glucopyranose 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 

Downstream Products

• 4356-77-8 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose 
• 110383-77-2 2,3,4-tri-O-benzyl-6-O-trimethylsilyl-α-D-glucopyranosyl bromide 
• 110398-04-4 2,3,4-tri-O-benzyl-6-O-triethylsilyl-α-D-glucopyranosyl bromidee 
• 124595-44-4 phenyl 2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-glucopyranoside 
• 120403-26-1 phenyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 87470-73-3 phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 130515-37-6 cyclohexyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 130515-38-7 cyclohexyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 120417-05-2 Carbonic acid ethyl ester (E)-3-((3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-propenyl ester 
• 120417-06-3 Acetic acid (E)-2-methyl-3-((3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-propenyl ester 
• 130515-94-5 methyl 2,3,6-tri-O-benzyl-4-thio-4-S-(2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 130515-43-4 methyl 2,3,6-tri-O-benzyl-4-thio-4-S-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 130515-44-5 1,6-anhydro-2,3-di-O-benzyl-4-O-<2,3,6-tri-O-benzyl-4-thio-4-S(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranosyl>-β-D-glucopyranose 
• 66963-55-1 1,6-anhydro-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranose 

Relevant articles and documents

Trimethylsilyl triflate mediated chemoselective condensation of arylsulfenyl glycosides

Condensation of a fully benzoylated phenylsulfenyl glycoside with either benzylated or benzoylated phenylthio glycosyl acceptors under the agency of trimethylsilyl triflate proceeds with a good degree of chemoselectivity in the presence of the scavenger t

Lewis-acidic polyoxometalates as reusable catalysts for the synthesis of glucuronic acid esters under microwave irradiation

Chemoselective microwave-assisted transesterification of 6,1-lactone derived from glucuronic acid is catalyzed by reusable Dawson-type polyoxometalates. These catalysts allow the formation of pseudo-disaccharides from easily available precursors. This permits the expeditious assembly of promising building blocks from precursors obtained from biomass, with easy recycling of the catalyst.

One-pot, highly stereoselective synthesis of dithioacetal-α,α-diglycosides

A one-step access to dithioacetal-α,α-diglycosides is reported. The synthetic strategy is based on the thioacetalization of aldehydes or ketones via highly stereoselective ring-opening of 1,6 anhydrosugars with bis(trimethylsilyl)sulfide.

Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside

We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.

Total synthesis of herbicidin C and aureonuclemycin: Impasses and new avenues

The undecose nucleoside antibiotics herbicidin C and aureonuclemycin are biologically highly active and represent challenging targets for total synthesis. Herein, the gradual evolution of our synthetic strategy toward these natural products is described in detail. The initial route encompasses metalate addition chemistry but suffers from poor stereochemical control. In contrast, the ultimately successful strategy benefits from a variety of reagent-controlled stereoselective transformations, including a surprisingly facile and highly diastereoselective N-glycosylation process. The presented work also describes new building blocks that might find further application in carbohydrate chemistry.

Synthesis of α-glycosyl thiols by stereospecific ring-opening of 1,6-anhydrosugars

Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of α-glycosyl thiols. All the reactions were highly stereoselective and afforded the α-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding α-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to α-glycosyl thiols of great value was established (Figure presented).

Gold-catalyzed glycosidations: Synthesis of 1,6-anhydro saccharides

Various 1,6-anhydro sugars are synthesized utilizing salient features of gold-catalyzed glycosidations. All the reactions occurred under mild conditions in the presence of 7 mol % of AuBr3 enabling easy synthesis of 1,6-anhydro sugars from corr

Methyl glycosides are identified as glycosyl donors for the synthesis of glycosides, disaccharides and oligosaccharides

Stable methyl glycosides are identified as glycosyl donors in the presence of AuBr3 in acetonitrile; a panel of aglycones comprising aliphatic, alicyclic, steroidal and sugar alcohols are examined successfully for the glycosylation reaction and

Formation of O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation

This paper describes the direct formation of various O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation. The condensation reactions of 1 -hydroxy sugars with some primary alcohols in the presence of on

Synthesis of pentasaccharide and heptasaccharide derivatives and their effects on plant growth

Two oligosaccharide derivatives, β-D-Glcp-(1-6)-β-D-Glcp-(1-6)- β-D-Glcp-(1-6)-β-D-Glcp-(1-4)-α-D-ManpOMe (1) and β-D-Glcp-(1-6)-β-D-Glcp-(1-6)-β-D-Glcp-(1-6)-β-D-Glcp-(1-6) -β-D-Glcp-(1-6)-β-D-Glcp-(1-4)-α-D-ManpOMe (2), have been synthesized efficiently using a convergent glycosylation strategy of 2 + 3 and 2 + 5.1,6-Anhydro-β-D-glucopyranose, which was prepared from cotton pyrolysis, was applied as a key synthon in the synthesis, significantly simplifying the preparation. The bioassay suggested that these two oligosaccharides can both stimulate the growth of maize cultured in liquid medium at a concentration of 3 ppm.