3,4-bis-O-benzyl-6-triisoporpylsilyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

Base Information

• Chemical Name: 3,4-bis-O-benzyl-6-triisoporpylsilyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose
• CAS No.: 1356163-67-1
• Molecular Formula: C₃₂H₄₈O₇Si
• Molecular Weight: 572.814
• Mol file: 1356163-67-1.mol

Synonyms:3,4-bis-O-benzyl-6-triisoporpylsilyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

Chemical Property of 3,4-bis-O-benzyl-6-triisoporpylsilyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-bis-O-benzyl-6-triisoporpylsilyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

There total 5 articles about 3,4-bis-O-benzyl-6-triisoporpylsilyl-1,2-O-(1-methoxyethylidene)-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: 89.0%

6-triisoporpylsilyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose (1356163-63-7) + benzyl bromide (100-39-0) → 3,4-bis-O-benzyl-6-triisoporpylsilyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose (1356163-67-1)

Guidance literature:

6-triisoporpylsilyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃;

DOI:10.1039/c2ob06827c

Reference yield:

3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose (3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0) → 3,4-bis-O-benzyl-6-triisoporpylsilyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose (1356163-67-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium methylate / methanol / 12 h / 0 - 20 °C

1.2: Dowex 50w X 8 [H⁺]

2.1: 1H-imidazole / dichloromethane / 17 h / 0 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

3.2: 0 - 20 °C

With 1H-imidazole; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c2ob06827c

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-bis-O-benzyl-6-triisoporpylsilyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose (1356163-67-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylsilane; iodine / dichloromethane / 0 °C / Reflux

2.1: 2,6-dimethylpyridine; tetra-(n-butyl)ammonium iodide / dichloromethane / 0 °C / Reflux

3.1: sodium methylate / methanol / 12 h / 0 - 20 °C

3.2: Dowex 50w X 8 [H⁺]

4.1: 1H-imidazole / dichloromethane / 17 h / 0 °C

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

5.2: 0 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; iodine; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c2ob06827c

upstream raw materials:

D-glucose pentaacetate

6-triisoporpylsilyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

benzyl bromide

3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose

Downstream raw materials:

Ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-β-D-glucopyranoside

3,4-di-O-benzyl-6-O-triisoporpylsilyl-S-thiaethyl-β-D-glucopyranose