methyl 2,3,4-tri-O-benzyl-6-O-(prop-2-ynyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-benzyl-6-O-(prop-2-ynyl)-α-D-glucopyranoside
• CAS No.: 250127-77-6
• Molecular Formula: C₃₁H₃₄O₆
• Molecular Weight: 502.607
• Mol file: 250127-77-6.mol

Synonyms:methyl 2,3,4-tri-O-benzyl-6-O-(prop-2-ynyl)-α-D-glucopyranoside

Chemical Property of methyl 2,3,4-tri-O-benzyl-6-O-(prop-2-ynyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4-tri-O-benzyl-6-O-(prop-2-ynyl)-α-D-glucopyranoside

There total 6 articles about methyl 2,3,4-tri-O-benzyl-6-O-(prop-2-ynyl)-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: 98.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + propargyl bromide (106-96-7) → methyl 2,3,4-tri-O-benzyl-6-O-(prop-2-ynyl)-α-D-glucopyranoside (250127-77-6)

Guidance literature:

In N,N-dimethyl-formamide; at 0 - 20 ℃; for 0.5h;

DOI:10.1016/j.bmcl.2020.127276

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → methyl 2,3,4-tri-O-benzyl-6-O-(prop-2-ynyl)-α-D-glucopyranoside (250127-77-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; pyridine / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C

2.2: 0 - 20 °C

3.1: camphor sulfonic acid / dichloromethane; methanol / 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C

4.2: 0 - 20 °C

With pyridine; dmap; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tetlet.2017.05.012

Reference yield:

methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside (166592-73-0) → methyl 2,3,4-tri-O-benzyl-6-O-(prop-2-ynyl)-α-D-glucopyranoside (250127-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride; benzyl bromide / N,N-dimethyl-formamide / 3 h / 0 - 70 °C

1.2: 3 h / 0 - 20 °C

2.1: N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C

With benzyl bromide; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2020.127276

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

propargyl bromide

methyl-alpha-D-glucopyranoside

methyl 6-O-trityl-α-D-glucopyranoside

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

methyl 6-O-allyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-[1-(4-acetylphenyl)-1H-1,2,3-triazol-4-ylmethyl] α-D-glucopyranoside

1,6-di-O-(methyl-2,3,4-tri-O-benzyl-6-yl-α-D-glucopyranoside)-2,4-hexadiyne