dimethyl t-hexylsilyl 2-acetamido-4,6-di-O-(4-methoxybenzylidene)-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: dimethyl t-hexylsilyl 2-acetamido-4,6-di-O-(4-methoxybenzylidene)-2-deoxy-β-D-glucopyranoside
• CAS No.: 1115586-42-9
• Molecular Formula: C₂₄H₃₉NO₇Si
• Molecular Weight: 481.662
• Mol file: 1115586-42-9.mol

Synonyms:dimethyl t-hexylsilyl 2-acetamido-4,6-di-O-(4-methoxybenzylidene)-2-deoxy-β-D-glucopyranoside

Chemical Property of dimethyl t-hexylsilyl 2-acetamido-4,6-di-O-(4-methoxybenzylidene)-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl t-hexylsilyl 2-acetamido-4,6-di-O-(4-methoxybenzylidene)-2-deoxy-β-D-glucopyranoside

There total 1 articles about dimethyl t-hexylsilyl 2-acetamido-4,6-di-O-(4-methoxybenzylidene)-2-deoxy-β-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:

N-{(2S,3R,4R,5S,6R)-2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide + 4-methoxy-benzaldehyde (123-11-5) → dimethyl t-hexylsilyl 2-acetamido-4,6-di-O-(4-methoxybenzylidene)-2-deoxy-β-D-glucopyranoside (1115586-42-9)

Guidance literature:

With pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1016/j.carres.2008.10.007

Reference yield: 68.0%

dimethyl t-hexylsilyl 2-acetamido-4,6-di-O-(4-methoxybenzylidene)-2-deoxy-β-D-glucopyranoside (1115586-42-9) + allyl bromide (106-95-6) → dimethyl t-hexylsilyl 2-acetamido-3-O-allyl-4,6-di-O-(4-methoxybenzylidene)-2-deoxy-β-D-glucopyranoside (1115586-43-0)

Guidance literature:

dimethyl t-hexylsilyl 2-acetamido-4,6-di-O-(4-methoxybenzylidene)-2-deoxy-β-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.166667h; Inert atmosphere;

allyl bromide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.carres.2008.10.007

Reference yield:

dimethyl t-hexylsilyl 2-acetamido-4,6-di-O-(4-methoxybenzylidene)-2-deoxy-β-D-glucopyranoside (1115586-42-9) → dimethyl t-hexylsilyl 2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranoside (1115586-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: sodium cyanoborohydride; trifluoroacetic acid / N,N-dimethyl-formamide / 0 - 20 °C / Molecular sieve

With sodium hydride; sodium cyanoborohydride; trifluoroacetic acid; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.carres.2008.10.007

upstream raw materials:

4-methoxy-benzaldehyde

Downstream raw materials:

dimethyl t-hexylsilyl 2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

dimethyl t-hexylsilyl 2-acetamido-3-O-allyl-4,6-di-O-(4-methoxybenzylidene)-2-deoxy-β-D-glucopyranoside