3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

Base Information

• Chemical Name: 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide
• CAS No.: 70831-94-6
• Molecular Formula: C20H20BrNO9
• Molecular Weight: 498.284
• Hs Code.: 2932990090
• DSSTox Substance ID: DTXSID30443608
• Mol file: 70831-94-6.mol

Synonyms:70831-94-6;3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide;[(2R,3S,4R,5R)-3,4-diacetyloxy-6-bromo-5-(1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate;BROMO 2-DEOXY-2-N-PHTHALIMIDO-3,4,6-TRI-O-ACETYL-ALPHA,BETA-D-GLUCOPYRANOSIDE;(2R,3S,4R,5R)-2-(Acetoxymethyl)-6-bromo-5-(1,3-dioxoisoindolin-2-yl)tetrahydro-2H-pyran-3,4-diyl diacetate;SCHEMBL8831058;DTXSID30443608;T-5923;Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl- alpha , beta -D-glucopyranoside;(2R,3S,4R,5R)-2-(Acetoxymethyl)-6-bromo-5-(1,3-dioxoisoindolin-2-yl)tetrahydro-2H-pyran-3,4-diyldiacetate;[(2R,3S,4R,5R)-3,4-bis(acetyloxy)-6-bromo-5-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)oxan-2-yl]methyl acetate

Chemical Property of 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 124-128°C
• Boiling Point: 567.14°C at 760 mmHg
• PKA: -2.57±0.20(Predicted)
• Flash Point: 296.796°C
• PSA: 125.51000
• Density: 1.594g/cm³
• LogP: 1.13540
• Storage Temp.: Amber Vial, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Sparingly), Dichloromethane (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 497.03214
• Heavy Atom Count: 31
• Complexity: 748

Purity/Quality:

97% ^*data from raw suppliers

Bromo2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside(Stabilizedwith~2%CaCO3) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)Br)N2C(=O)C3=CC=CC=C3C2=O)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)Br)N2C(=O)C3=CC=CC=C3C2=O)OC(=O)C)OC(=O)C
• Uses: Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside is used for the synthesis of ?-D-N-acetyl glucosamine glycosidic linkages.

Technology Process of 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

There total 10 articles about 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide 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: 96.0%

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-D-glucopyranosyl bromide (70831-94-6) + 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (10028-45-2)

Guidance literature:

With Acetyl bromide; boron trifluoride diethyl etherate; zinc(II) iodide; In chloroform; at 50 ℃; for 4h; Yields of byproduct given. Title compound not separated from byproducts;

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

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1) → 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide (70831-94-6)

Guidance literature:

With hydrogen bromide; In dichloromethane; acetic acid; at 0 - 20 ℃; for 3.5h;

Reference yield:

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-D-glucopyranosyl bromide (70831-94-6)

Guidance literature:

With hydrogen bromide; In acetic anhydride; acetic acid; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(01)00196-X

upstream raw materials:

2-deoxy-2-phthalimido-D-glucopyranose

acetic anhydride

4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside

methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside

Benzyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-desoxy-6-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranosid

4-O-benzyl-1,2-O-benzylidene-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-rhamnopyranose

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl 4-O-benzyl-2,3-O-benzylidene-β-L-rhamnopyranoside

Refernces

• 1、 -. "CARBOHYDRATE-MODIFIED GLYCOPROTEINS AND USES THEREOF". . . Retrieved 2014/10/04.
• 2、 Shao, Ning,Xue, Jie,Guo, Zhongwu. "Chemical Synthesis of CD52 Glycopeptides Containing the Acid-Labile Fucosyl Linkage". . p. 9003 - 9011. Retrieved 2007/10/03.