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

Chemical Properties

White Solid

Uses

Chloro 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside (cas# 7772-87-4) is a compound useful in organic synthesis.

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

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

Downstream Products

• 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 
• 77345-44-9 benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 73821-89-3 Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranosid 
• 80599-52-6 methyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside 
• 80612-72-2 methyl 4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-α-D-mannopyranoside 
• 80658-58-8 methyl 6-O-(2-acetamide-2-deoxy-β-D-glucopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside 
• 111462-66-9 β-D-GlcpNAc-(1->6)-α-D-Manp-OMe 
• 149359-37-5 benzyl (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-octyloxypropanoate 
• 149359-31-9 diethyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonate 
• 149359-32-0 (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)methylphosphonic acid 
• 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 
• 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 
• 80035-31-0 benzyl 2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 

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.

Differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-d-glucopyranosyl chlorides and their application in the synthesis of diosgenyl 2-amino-2-deoxy-β-d-glucopyranoside

Four differently N-protected 3,4,6-tri-O-acetyl-2-amino-2-deoxy-d- glucopyranosyl chlorides were synthesized and used as glycosyl donors in reactions with diosgenin. The following amine group protections were tested: trifluoroacetyl (TFA), 2,2,2-trichloroethoxycarbonyl (Troc), phthaloyl (Phth), and tetrachlorophthaloyl (TCP). Products of glycosylation were deprotected to yield diosgenyl 2-amino-2-deoxy-β-d-glucopyranoside. The efficiency of the procedures is discussed. Additionally, a single-crystal X-ray diffraction analysis for 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-β-d- glucopyranosyl chloride is reported. Orientations of the pyranose substituents as well as the planarity of the acetoxy and phthalimide groups in the crystal lattice are discussed. Structural evidence is presented for a mesomeric effect in both groups. The preference of the cis over trans orientation of the acetoxy group is confirmed in the crystal lattice.

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.