6167-32-4

Usage

Chemical class

Carbohydrate derivative

Structure

Cyclic ether with a tosyl group attached to the O atom at position 2

Functional groups

Tosyl (-OTs) group

Stereochemistry

Beta-D-galactopyranose

Application

Organic synthesis and as a building block for more complex molecules

Reactivity

Valuable tool for carbohydrate chemistry due to its unique structure and reactivity

Potential applications

Pharmaceuticals and material science

Research interest

Ability to form glycosidic bonds and creation of novel synthetic carbohydrates

These properties and specific content provide a comprehensive overview of 1,6

3,4-Dianhydro-2-O-tosyl-beta-D-galactopyranose, highlighting its chemical characteristics, applications, and research significance.

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 34147-09-6 1,6:3,4-dianhydro-β-D-talopyranose 
• 498-07-7 levoglucosan 
• 16939-77-8 1,6:3,4-dianhydro-β-D-galactopyranose 
• 50880-93-8 levoglucosan tritosylate 
• 20204-80-2 [(1R,2S,3S,4R,5R)-3-hydroxy-4-(p-tolylsulfonyl)-6,8-dioxabicyclo[3.2.1]oct-2-yl]-4-methylbenzenesulfonic acid 
• 5349-02-0 1,6-Anhydro-2,3-O-isopropylidene-4-O-p-toluenesulfonyl-β-D-mannopyranose 
• 40245-97-4 O⁴-(toluene-4-sulfonyl)-1,6-anhydro-β-D-mannopyranose 

Downstream Products

• 139147-87-8 1,6-anhydro-4-O-(11-hydroxy-3,6,9-trioxaundecyl)-2-O-p-toluenesulfonyl-β-D-glucopyranose 
• 85433-11-0 (1S,2S,3S,4R,5R)-2-methyl-4-<(p-toluenesulfonyl)-oxy>-6,8-dioxabicyclo<3.2.1>octan-3-ol 
• 110104-40-0 (1S,2S,3S,4R,5R)-2-Ethyl-4-(p-toluenesulfonyl)oxy-6,8-dioxabicyclo<3.2.1>octan-3-ol 
• 110104-41-1 (1S,2S,3S,4R,5R)-2-(2-Methyl-2-propenyl)-4-(p-toluenesulfonyl)oxy-6,8-dioxabicyclo<3.2.1>octan-3-ol 
• 74878-90-3 Toluene-4-sulfonic acid (1S,2S,3S,4R,5R)-2-allyl-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester 
• 53434-69-8 1,6-anhydro-4-deoxy-4-iodo-2-O-p-toluenesulfonyl-β-D-glucopyranose 
• 23643-30-3 1,6-anhydro-4-deoxy-2-O-p-toluenesulphonyl-β-D-xylo-hexopyranose 
• 53716-80-6 1,6-anhydro-3,4-dideoxy-2-O-p-toluenesulfonyl-β-D-erythro-hex-3-enopyranose 
• 77015-91-9 1,6-Anhydro-4-brom-4-desoxy-2-O-tosyl-β-D-glucopyranose 
• 77015-90-8 1,6-Anhydro-4-chlor-4-desoxy-2-O-tosyl-β-D-glucopyranose 
• 77015-92-0 1,6-Anhydro-4-thiocyanato-4-desoxy-2-O-tosyl-β-D-glucopyranose 
• 84207-46-5 3,4-di-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose 
• 84207-47-6 4-O-acetyl-1,6-anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose 
• 39697-97-7 4-O-Allyl-1,6-anhydro-2-O-tosyl-β-D-glucopyranose 

Relevant academic research and scientific papers

1,6-ANHYDROGLUCOSE IN ORGANIC SYNTHESIS; PREPARATION OF FRAGMENTS SUITABLE FOR NATURAL PRODUCT SYNTHESIS

1,6-Anhydroglucose has been used for the stereocontrolled preparation of optically active units which should be suitable for the synthesis of propionate-derived natural products.

Easy access to a carbohydrate-based template for stimuli-responsive surfactants

In this paper we describe the synthesis of a new carbohydrate-based building block functionalized with azido or amino groups on the 2 and 4 positions. The building block can be synthesized in anomerically pure form in only five scalable steps starting fro

Exploring the Chemistry of Non-sticky Sugars: Synthesis of Polyfluorinated Carbohydrate Analogues of d-Allopyranose

There is a growing interest in the preparation of polyfluorinated carbohydrates. A limited number of fluorohexopyranosides have been used in biological investigations because of the synthetic challenge they present. Hence, we report the synthesis of fluor

Preparation method of fondaparinux sodium monosaccharide intermediate

The invention discloses a preparation method of a fondaparinux sodium monosaccharide intermediate. The preparation method comprises the following steps: (1) in the presence of an acid-binding agent, carrying out esterification reaction on a compound as shown in a formula (I) and a substituent sulfonic anhydride and/or a substituent sulfonyl halogen to generate a compound as shown in a formula (II); (2) carrying out a ring opening reaction on the compound as shown in the formula (II) in an acidic condition to generate a compound as shown in a formula (III); (3) carrying out benzylation reactionon the compound as shown in the formula (III) and benzyl monohalide in an alkaline condition to generate a compound as shown in a formula (IV); and (4) carrying out an azido reaction on the compoundas shown in the formula (IV) and alkali metal azide salt to generate a compound as shown in a formula (V) and caring out inner ether ring opening and acetylation reaction on the compound as shown in the formula (V) in a mixed solution of acetic anhydride and trifluoroacetic acid to generate a compound as shown in a formula (VI). The method can be used for obtaining an ideal product yield, and theraw materials are cheap, easily available and relatively few in three wastes. The formulae are as shown in the description.

Synthesis of Protected 3-Deoxy-3-fluoro- and 4-Deoxy-4-fluoro-d-galactopyranosides from Levoglucosan

Fluorinated carbohydrates are invaluable tools to study various biochemical processes. Herein, we describe a new strategy to access orthogonally protected 3-deoxy-3-fluorogalactopyranose and acetylated 4-deoxy-4-fluorogalactopyranose. Starting from inexpensive levoglucosan, most reactions were performed on a gram scale and allowed excellent regio- and stereocontrol with a minimal use of protection/deprotection cycles. Hence, we developed practical alternatives to the decade-long reported method to access both 3-deoxy-3-fluoro- and 4-deoxy-4-fluorogalactopyranose.

Synthesis and glycosidase inhibitory activity of noeurostegine - A new and potent inhibitor of β-glucoside hydrolases

A new, stable hemi-aminal nor-tropane christened noeurostegine was synthesised in 22 steps from levoglucosan and tested for inhibitory activity against glycoside hydrolases. Sweet almond and Thermotoga maritimaβ- glucosidases, coffee bean α-galactosidase,

New derivatives of levoglucosan by tandem epoxide allyl alcohol rearrangement-cuprate cross-coupling

The alkylated allyl alcohols 6a, 7, and 8 (R = Me, Et, nBu) were formed in the reaction of the Cerny epoxide 3 with the Cyano-Gilman cuprates. The one-pot reaction was initiated by base-catalyzed epoxide allyl alcohol rearrangement to compound 5, followed

MEVINIC ACIDS AND ANALOGS : A NOVEL EFFICIENT ROUTE TO CHIRAL SYNTHONS FROM 1,6-ANHYDRO-D-GLUCOSE

1,6-anhydro-D-glucose is efficiently and regioselectively deoxygenated at C-2 and C-4 by displacement of the corresponding ditosylate with thiophenol followed by Raney Ni hydrogenolysis.This route provides a short access to chirons of the key lactonic moi

SYNTHESES OF 3-DEOXY-3-SUBSTITUTED-D-GLUCOSE DERIVATIVES. PART I. IMPROVEMENTS IN PREPARATION OF AND NUCLEOPHILIC ADDITIONS TO 1,6:2,3-DIANHYDRO-4-O-BENZYL-Β-D-ALLOPYRANOSE

The yield of the five-step preparation of 1,6:2,3-dianhydro-4-O-benzyl-β-D-glucopyranose from 1,6-anhydro-β-D-glucopyranose has been raised to 33percent from 12percent by modifying conditions or methods for four of the steps.It has been demonstrated that