4-O-beta-D-Galactopyranosyl-alpha-D-glucopyranosyl fluoride

Base Information

• Chemical Name: 4-O-beta-D-Galactopyranosyl-alpha-D-glucopyranosyl fluoride
• CAS No.: 7792-96-3
• Molecular Formula: C₁₂H₂₁FO₁₀
• Molecular Weight: 344.291

Synonyms:4-O-beta-D-Galactopyranosyl-alpha-D-glucopyranosyl fluoride;alpha-Lactopyranosyl fluoride

Chemical Property of 4-O-beta-D-Galactopyranosyl-alpha-D-glucopyranosyl fluoride

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-beta-D-Galactopyranosyl-alpha-D-glucopyranosyl fluoride

There total 9 articles about 4-O-beta-D-Galactopyranosyl-alpha-D-glucopyranosyl 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%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl fluoride (440-02-8,440-03-9,4089-50-3,14227-57-7,14227-61-3,14227-64-6,14877-70-4,71328-29-5,106758-57-0,132076-76-7) → 4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl fluoride (7584-85-2,7792-96-3,30048-41-0,71328-30-8,103531-01-7,149342-82-5,66701-54-0)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 6h;

DOI:10.3762/bjoc.8.51

Reference yield: 71.0%

O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl fluoride (14227-57-7) → β-D-galactopyranosyl-(1->4)-α-D-glucopyranosyl fluoride (7584-85-2,7792-96-3,30048-41-0,66701-54-0,71328-30-8,103531-01-7,149342-82-5)

Guidance literature:

With sodium methylate;

DOI:10.1016/0008-6215(93)84062-B

Reference yield:

1,2,3,6,2',3',4',6'-octa-O-acetylmaltose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4,20880-60-8) → 4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl fluoride (7584-85-2,7792-96-3,30048-41-0,71328-30-8,103531-01-7,149342-82-5,66701-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen fluoride

2: sodium methoxide / methanol / 0 °C

With hydrogen fluoride; sodium methylate; In methanol;

DOI:10.1016/S0008-6215(00)90223-4

upstream raw materials:

1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose

O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl fluoride

lactose octaacetate

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl fluoride

Downstream raw materials:

2,3,6-Tri-O-(dideutero-phenylmethyl)-4-O-<2,3,4,6-tetra-O-(dideutero-phenylmethyl)-β-D-galactopyranosyl>-α-D-glucopyranosyl fluoride

2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosyl fluoride

O-(β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosyl)-(1→1)-(2S, 3R, 4E)-2-aminooctadec-4-ene-1,3-diol

maltosyl(α1->6)α-cyclodextrin

Refernces

Highly efficient synthesis of β(1 → 4)-oligo- and -polysaccharides using a mutant cellulase

10.1021/ja9936520

The research focuses on the efficient chemoenzymatic synthesis of various regioselectively modified β(1f4)-oligo- and -polysaccharides using a mutant cellulase. The experiments are based on the use of a "glycosynthase," which is a Glu-197-Ala nucleophile mutant of the retaining cellulase endoglucanase I (Cel7B) from Humicola insolens. The methodology involves the rational design of modified acceptor and donor molecules, informed by X-ray structures of wild type and mutated enzymes. Reactants include R-glycobiosyl fluorides, various mono- and disaccharide acceptors, and the polymerization of these donors through a single-step inverting mechanism. Lactosyl fluoride was used as a donor substrate in the synthesis of various oligosaccharides. The analyses used to characterize the synthesized oligo- and polysaccharides encompass techniques such as NMR spectroscopy, mass spectrometry, enzymatic hydrolysis, and in some cases, X-ray crystallography. The study demonstrates the mutant enzyme's ability to catalyze the regio- and stereoselective glycosylation of various acceptors with high yield, showcasing a highly efficient approach for the synthesis of β(1f4)-oligosaccharides and polysaccharides.

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