methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside
• CAS No.: 141438-53-1
• Molecular Formula: C₃₀H₃₃NO₈
• Molecular Weight: 535.594
• Mol file: 141438-53-1.mol

Synonyms:methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside

Chemical Property of methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside

There total 3 articles about methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 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: 67.0%

benzyl bromide (100-39-0) + methyl 2--2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside (141438-52-0) → methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside (141438-53-1)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium hydride; In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1021/jo00039a044

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside (141438-53-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / camphorsulfonic acid / dimethylformamide / 4 h / 90 °C

2: 67 percent / KH, n-Bu₄NI / tetrahydrofuran / 1.5 h / 0 °C

With camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; potassium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo00039a044

Reference yield:

((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (4704-15-8) → methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside (141438-53-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / camphorsulfonic acid / dimethylformamide / 4 h / 90 °C

2: 67 percent / KH, n-Bu₄NI / tetrahydrofuran / 1.5 h / 0 °C

With camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; potassium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo00039a044

upstream raw materials:

benzyl bromide

methyl 2--2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside

p-Anisaldehyde dimethyl acetal

((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

Downstream raw materials:

methyl 4-O-acetyl-2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside

(2S,3R,4R)-4-acetoxy-3-benzyloxy-2--5-hexen-1-ol

methyl 2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside

(2S,3R,4R)-4-acetoxy-3-benzyloxy-2--5-hexenal