3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose
• CAS No.: 158852-31-4
• Molecular Formula: C₃₁H₃₆O₇
• Molecular Weight: 520.623
• Mol file: 158852-31-4.mol

Synonyms:3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose

Chemical Property of 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose

There total 5 articles about 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose 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: 98.0%

benzyl bromide (100-39-0) + 3,4,6-tri-O-acetyl-1,2-O-<1-(exo-ethoxy)ethylidene>-α-D-glucopyranose (38081-38-8) → 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose (158852-31-4)

Guidance literature:

3,4,6-tri-O-acetyl-1,2-O-<1-(exo-ethoxy)ethylidene>-α-D-glucopyranose; With methanol; sodium; at 20 ℃; for 1h; Inert atmosphere;

benzyl bromide; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 15h; Inert atmosphere;

DOI:10.1021/jacs.1c07135

Reference yield:

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose (158852-31-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: iodine; triethylsilane / dichloromethane / 1 h / Inert atmosphere; Reflux

1.2: 3 h / Inert atmosphere; Reflux

2.1: methanol; sodium / 1 h / 20 °C / Inert atmosphere

2.2: 15 h / 0 - 20 °C / Inert atmosphere

With methanol; triethylsilane; iodine; sodium; In dichloromethane;

DOI:10.1021/jacs.1c07135

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose (158852-31-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Bu₄NBr; s-collidine

2: 81 percent / KOH / tetrahydrofuran

With 2,4,6-trimethyl-pyridine; potassium hydroxide; tetrabutylammomium bromide; In tetrahydrofuran; 1: Cyclization / 2: Etherification;

DOI:10.1021/jo9800098

upstream raw materials:

benzyl bromide

3,4,6-tri-O-acetyl-1,2-O-<1-(exo-ethoxy)ethylidene>-α-D-glucopyranose

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

1,2-O-(1-ethoxyethylidene)-α-D-glucopyranose

Downstream raw materials:

2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside