3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE

Base Information

• Chemical Name: 3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE
• CAS No.: 7772-87-4
• Molecular Formula: C20H20ClNO9
• Molecular Weight: 453.833
• Mol file: 7772-87-4.mol

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

Chemical Property of 3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 146-147oC
• Boiling Point: 563.161°C at 760 mmHg
• Flash Point: 294.389°C
• PSA: 125.51000
• Density: 1.461g/cm³
• LogP: 0.97930
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

99%min ^*data from raw suppliers

3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranosyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of 3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE

There total 13 articles about 3,4,6-TRI-O-ACETYL-2-DEOXY-2-FLUORO-D-MANNOPYRANOSYL FLUORIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside (138906-41-9) → 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride (7772-87-4) + 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α/β-D-glucopyranosyl chloride (187022-30-6)

Guidance literature:

With boron trifluoride diethyl etherate; acetyl chloride; zinc(II) iodide; In chloroform; at 50 ℃; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0008-6215(96)90118-4

Reference yield: 92.0%

4-chlorophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (296768-92-8) → 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride (7772-87-4)

Guidance literature:

With diphenylchlorosulfonium chloride; In dichloromethane; at -78 - 20 ℃; for 1.5h;

DOI:10.1021/ol0063050

Reference yield: 91.5%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride (7772-87-4)

Guidance literature:

With phosphorus pentachloride; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1080/07328303.2014.996290

upstream raw materials:

N-ethoxycarbonylphthalimide

(+)-D-glucosamine hydrochloride

acetyl chloride

2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

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

C₁₂₈H₁₃₃N₃O₄₃

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

Refernces

• 1、 Cao, Zhiling,Qu, Yingying,Zhou, Jiexing,Liu, Weiwei,Yao, Guowei. "Stereoselective Synthesis of Quercetin 3-O-Glycosides of 2-Amino-2-Deoxy-d-Glucose under Phase Transfer Catalytic Conditions". . p. 28 - 40. Retrieved 2015/10/20.
• 2、 Cao, Zhiling,Liu, Wenjie,Qu, Yingying,Yao, Guowei,Gao, Dachao,Liu, Weiwei. "A facile and stereoselective synthesis of 3,4,6-tri-O-acetyl-2-deoxy-2- phthalimido-β-D-glucopyranosyl chloride". . p. 467 - 469. Retrieved 2013/09/12.