methyl 2-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside
• CAS No.: 1352406-78-0
• Molecular Formula: C₂₀H₃₂O₅Si
• Molecular Weight: 380.557
• Mol file: 1352406-78-0.mol

Synonyms:methyl 2-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

Chemical Property of methyl 2-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

There total 3 articles about methyl 2-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-benzylidene-3-deoxy-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: 100.0%

p-methoxybenzyl chloride (824-94-2) + methyl 4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside (65530-28-1) → methyl 2-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside (1352406-78-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 22h;

DOI:10.1016/j.bmcl.2011.10.005

Reference yield:

methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside (65556-00-5) → methyl 2-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside (1352406-78-0)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 24 h / Reflux

2: sodium hydride / tetrahydrofuran / 22 h / 20 °C

With lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2011.10.005

Reference yield:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 2-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside (1352406-78-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 72 h / 20 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 24 h / Reflux

3: sodium hydride / tetrahydrofuran / 22 h / 20 °C

With pyridine; lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2011.10.005

upstream raw materials:

methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside

p-methoxybenzyl chloride

methyl 4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

Downstream raw materials:

methyl 4-O-benzyl-3-deoxy-α-D-gluco-hexodialdo-1,5-pyranoside

methyl 4-O-benzyl-3-deoxy-α-D-ribo-hexopyranoside

benzyl alcohol