benzyl 2-acetamido-3,6-di-O-benzyl-4-O-propargyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-3,6-di-O-benzyl-4-O-propargyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 1287768-23-3
• Molecular Formula: C₃₂H₃₅NO₆
• Molecular Weight: 529.633
• Mol file: 1287768-23-3.mol

Synonyms:benzyl 2-acetamido-3,6-di-O-benzyl-4-O-propargyl-2-deoxy-β-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-3,6-di-O-benzyl-4-O-propargyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-acetamido-3,6-di-O-benzyl-4-O-propargyl-2-deoxy-β-D-glucopyranoside

There total 11 articles about benzyl 2-acetamido-3,6-di-O-benzyl-4-O-propargyl-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: 88.0%

benzyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-β-D-glucopyranoside (62867-63-4) + propargyl bromide (106-96-7) → benzyl 2-acetamido-3,6-di-O-benzyl-4-O-propargyl-2-deoxy-β-D-glucopyranoside (1287768-23-3)

Guidance literature:

With barium(II) hydroxide; barium(II) oxide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/jo200076z

Reference yield:

benzyl bromide (100-39-0) → benzyl 2-acetamido-3,6-di-O-benzyl-4-O-propargyl-2-deoxy-β-D-glucopyranoside (1287768-23-3)

Guidance literature:

Multi-step reaction with 3 steps

1: barium(II) hydroxide; barium(II) oxide / N,N-dimethyl-formamide / 0 - 20 °C

2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 °C

3: barium(II) hydroxide; barium(II) oxide / N,N-dimethyl-formamide / 0 - 20 °C

With triethylsilane; boron trifluoride diethyl etherate; barium(II) hydroxide; barium(II) oxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo200076z

Reference yield:

benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside (3055-51-4,3554-93-6,10380-86-6,13343-62-9,13343-67-4,19374-70-0,33423-30-2,33501-36-9,41355-95-7,86834-14-2,111003-11-3,347411-88-5) → benzyl 2-acetamido-3,6-di-O-benzyl-4-O-propargyl-2-deoxy-β-D-glucopyranoside (1287768-23-3)

Guidance literature:

Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C

2: barium(II) hydroxide; barium(II) oxide / N,N-dimethyl-formamide / 0 - 20 °C

3: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 °C

4: barium(II) hydroxide; barium(II) oxide / N,N-dimethyl-formamide / 0 - 20 °C

With triethylsilane; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; barium(II) hydroxide; barium(II) oxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo200076z

upstream raw materials:

benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside

benzyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-β-D-glucopyranoside

propargyl bromide

benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

C₅₃H₅₄N₄O₁₄

C₅₆H₅₆N₄O₁₄

C₅₅H₅₈N₄O₁₅

C₃₆H₃₉N₇O₁₅