7772-87-4

Basic information

• Product Name: 3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE
• Synonyms: 3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE;3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranosylchloride;2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-β-D-glucopyranosyl Chloride 3,4,6-Triacetate;2-Deoxy-2-phthaliMido-β-D-glucopyranosyl Chloride 3,4,6-Triacetate;Chloro 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-2-D-glucopyranoside
• CAS NO: 7772-87-4
• Molecular Formula: C₂₀H₂₀ClNO₉
• Molecular Weight: 453.829
• Product Categories: Aromatics;Carbohydrates & Derivatives;Heterocycles
• Mol File: 7772-87-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 146-147oC
• Boiling Point: 563.161°C at 760 mmHg
• Flash Point: 294.389°C
• Appearance: /
• Density: 1.461g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Stability: Keep dry
• CAS DataBase Reference: 3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE(7772-87-4)
• EPA Substance Registry System: 3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE(7772-87-4)

Safety Data

• Hazardous Substances Data: 7772-87-4(Hazardous Substances Data)

Usage

Description

3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE is a synthetic compound that is used as an intermediate in organic synthesis. It is a derivative of D-mannopyranose, a monosaccharide, with three acetyl groups attached to the 3, 4, and 6 positions and a fluorine atom at the 2 position. 3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE is characterized by its unique structure and properties, making it a valuable building block in the synthesis of various complex organic molecules.

Uses

Used in Organic Synthesis:
3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE is used as a synthetic intermediate for the preparation of complex organic molecules. Its unique structure and properties make it a valuable building block in the synthesis of various compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE is used as a key intermediate in the synthesis of various drug candidates. Its unique structure allows for the development of novel therapeutic agents with improved pharmacological properties, such as enhanced potency, selectivity, and bioavailability.
Used in Agrochemical Industry:
3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE is also used in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its unique structure can be utilized to develop novel compounds with improved efficacy, selectivity, and environmental compatibility.
Used in Specialty Chemicals Industry:
In the specialty chemicals industry, 3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE is used as a building block for the synthesis of various specialty chemicals, such as fragrances, dyes, and other functional materials. Its unique structure and properties enable the development of innovative products with unique properties and applications.

InChI:InChI=1/C20H20ClNO9/c1-9(23)28-8-14-16(29-10(2)24)17(30-11(3)25)15(18(21)31-14)22-19(26)12-6-4-5-7-13(12)20(22)27/h4-7,14-18H,8H2,1-3H3/t14?,15-,16+,17+,18+/m0/s1

Upstream product

• 22509-74-6 N-ethoxycarbonylphthalimide 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 75-36-5 acetyl chloride 
• 117252-69-4 2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 138906-41-9 4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 296768-92-8 4-chlorophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-phthalimido-2-deoxy-α-D-glucopyranose 
• 72858-55-0 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 

Downstream Products

• 80596-06-1 methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 80599-55-9 methyl 3,6-di-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranoside 
• 80599-54-8 methyl 2,4-di-O-benzyl-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranoside 
• 80599-51-5 methyl 6-O-benzoyl-2,4-di-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranoside 
• 79331-00-3 C₁₂₈H₁₃₃N₃O₄₃ 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 72858-55-0 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 112289-92-6 benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 112302-57-5 3,4,6,3',4',6'-hexa-O-acetyl-2,2'-dideoxy-2,2'-diphthalimido-β,β-trehalose 
• 81415-16-9 8-methoxycarbonyloctyl 2-(N-acetylbenzamido)-3,4-di-O-benzoyl-2-deoxy-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-galactopyranoside 
• 149359-30-8 diethyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate 
• 80035-31-0 benzyl 2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 296769-11-4 4-chlorophenyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 828930-51-4 benzyl (2R,3'R)-3-((2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methyl-hydroxy-phosphinoyloxy)-2-(3',7'-dimethyloctyloxy)propanoate 

Relevant articles and documents

Synthesis of glycosyl chlorides using catalytic Appel conditions

The stereoselective synthesis of glycosyl chlorides using catalytic Appel conditions is described. Good yields of α-glycosyl chlorides were obtained using a range of glycosyl hemiacetals, oxalyl chloride and 5 mol% Ph3PO. For 2-deoxysugars treatment of the corresponding hemiacetals with oxalyl chloride without phosphine oxide catalyst also gave good yields of glycosyl chloride. The method is operationaly simple and the 5 mol% phosphine oxide by-product can be removed easily. Alternatively a one-pot, multi-catalyst glycosylation can be carried out to transform the glycosyl hemiacetal directly to a glycoside.

A facile and stereoselective synthesis of 3,4,6-tri-O-acetyl-2-deoxy-2- phthalimido-β-D-glucopyranosyl chloride

Acetylation of D-glucosamine catalysed by sulfuric acid and N-phthaloylation of the glucosyl acetate yielded 1,3,4,6- tetra-O-acetyl-2- deoxy-2-phthalimido-α-D-glucopyranose. This gave the corresponding pure β-glucosyl chloride upon treatment with PCl5-BF3. An anomeric chlorination with thionyl chloride combined with the Lewis acids (ZnCl2, SnCl4 and BiCl3) resulted in an α/β anomer mixture.

A convenient preparation of glycosyl chlorides from aryl/alkyl thioglycosides

(equation presented) Because of the vast structural diversity encountered in the field of glycobiology, versatile methods for orthogonal oligosaccharide assembly are always of interest. Reported herein is the preparation of glycosyl chloride donors obtained by reaction of the corresponding thioglycoside precursors with chlorosulfonium chloride reagent 4. The crude chlorides thus obtained can be used directly in subsequent glycosylation reactions, and examples of the generality of this approach are provided.