1-O,2-O-[(R)-Benzylidene]-α-D-glucopyranose triacetate

Base Information

• Chemical Name: 1-O,2-O-[(R)-Benzylidene]-α-D-glucopyranose triacetate
• CAS No.: 38081-39-9
• Molecular Formula: C₁₉H₂₂O₉
• Molecular Weight: 394.378
• Mol file: 38081-39-9.mol

Synonyms:1-O,2-O-[(R)-Benzylidene]-α-D-glucopyranose triacetate

Chemical Property of 1-O,2-O-[(R)-Benzylidene]-α-D-glucopyranose triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O,2-O-[(R)-Benzylidene]-α-D-glucopyranose triacetate

There total 7 articles about 1-O,2-O-[(R)-Benzylidene]-α-D-glucopyranose triacetate 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:

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) → 3,4,6-tri-O-acetyl-1,2-O-<(R)-benzylidene>-α-D-glucopyranose (38081-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / sodium borohydride; potassium iodide / acetonitrile / 20 h / 20 °C

2: sodium methoxide / methanol

3: pyridine

With pyridine; sodium tetrahydroborate; sodium methylate; potassium iodide; In methanol; acetonitrile;

DOI:10.1081/CAR-120020483

Reference yield:

3,4,6-tri-O-benzoyl-1,2-O-benzylidene-α-D-glucopyranose (103664-30-8) → 3,4,6-tri-O-acetyl-1,2-O-<(R)-benzylidene>-α-D-glucopyranose (38081-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methoxide / methanol

2: pyridine

With pyridine; sodium methylate; In methanol;

DOI:10.1081/CAR-120020483

Reference yield:

1,3,4,6-tetra-O-acetyl-2-O-benzoyl-α-D-glucopyranoside (102219-46-5) → 3,4,6-tri-O-acetyl-1,2-O-<(R)-benzylidene>-α-D-glucopyranose (38081-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / hydrogen bromide / acetic acid; CH₂Cl₂ / 1 h

2: 1.) silver triflate, 2.) tetarbutylammonium borohydride / 1.) nitromethane, toluene, -25 deg C, 5 min, 2.) -25 deg C, 10 min

With hydrogen bromide; silver trifluoromethanesulfonate; tetrabutylammonium borohydride; In dichloromethane; acetic acid;

upstream raw materials:

2-O-benzoyl-3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

1,2-O-Benzyliden-α-D-glucopyranose

acetic anhydride

2,3,4,6-tetra-O-benzoylglucosyl bromide

Refernces

• 1、 Garegg, Per. J.,Konradsson, Peter,Kvarnstroem, Ingemar,Norberg, Thomas,Svensson, Stefan C. T.,Wigilius, Bo. "Studies on Koenigs-Knorr Glycosidations". . p. 569 - 578. Retrieved 2007/10/02.