methyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-α-D-glucopyranoside
• CAS No.: 876345-22-1
• Molecular Formula: C₁₆H₂₀BrN₃O₅
• Molecular Weight: 414.256
• Mol file: 876345-22-1.mol

Synonyms:methyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-α-D-glucopyranoside

Chemical Property of methyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-α-D-glucopyranoside

There total 1 articles about methyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-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: 90.0%

methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-glucopyranoside (861819-27-4) + 2-Bromoacetyl bromide (598-21-0) → methyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-α-D-glucopyranoside (876345-22-1)

Guidance literature:

With tetramethylurea; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2005.10.056

Reference yield: 93.0%

methyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-α-D-glucopyranoside (876345-22-1) + acetic anhydride (108-24-7) → 1-O-acetyl-4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-D-glucopyranoside (876345-23-2)

Guidance literature:

With sulfuric acid; acetic acid; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2005.10.056

Reference yield:

methyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-α-D-glucopyranoside (876345-22-1) → ethyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-1-thio-α-D-glucopyranoside

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / H₂SO₄; AcOH / 1 h / 20 °C

2: 23 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / 20 °C

With sulfuric acid; boron trifluoride diethyl etherate; acetic acid; In dichloromethane;

DOI:10.1016/j.bmcl.2005.10.056

upstream raw materials:

methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-glucopyranoside

2-Bromoacetyl bromide

Downstream raw materials:

1-O-acetyl-4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-D-glucopyranoside

ethyl 4-azido-3-O-benzyl-2-O-(bromoacetyl)-4,6-dideoxy-1-thio-β-D-glucopyranoside