2-azido-4,6-O-benzylidene-1-O-tert-butyldimethylsilyl-2-deoxy-3-O-(2-naphthalenylmethyl)-D-glucopyranoside

Base Information

• Chemical Name: 2-azido-4,6-O-benzylidene-1-O-tert-butyldimethylsilyl-2-deoxy-3-O-(2-naphthalenylmethyl)-D-glucopyranoside
• CAS No.: 1448013-28-2
• Molecular Formula: C₃₀H₃₇N₃O₅Si
• Molecular Weight: 547.726
• Mol file: 1448013-28-2.mol

Synonyms:2-azido-4,6-O-benzylidene-1-O-tert-butyldimethylsilyl-2-deoxy-3-O-(2-naphthalenylmethyl)-D-glucopyranoside

Chemical Property of 2-azido-4,6-O-benzylidene-1-O-tert-butyldimethylsilyl-2-deoxy-3-O-(2-naphthalenylmethyl)-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-4,6-O-benzylidene-1-O-tert-butyldimethylsilyl-2-deoxy-3-O-(2-naphthalenylmethyl)-D-glucopyranoside

There total 3 articles about 2-azido-4,6-O-benzylidene-1-O-tert-butyldimethylsilyl-2-deoxy-3-O-(2-naphthalenylmethyl)-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: 91.0%

2-azido-4,6-O-benzylidene-2-deoxyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside (138923-10-1) + 2-bromomethylnaphthyl bromide (939-26-4) → 2-azido-4,6-O-benzylidene-1-O-tert-butyldimethylsilyl-2-deoxy-3-O-(2-naphthalenylmethyl)-D-glucopyranoside (1448013-28-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.202000923

Reference yield:

tert-butyldimethylsilyl-2-azido-2-deoxy-3,4,6-tri-O-trimethylsilyl-β-D-glucopyranoside → 2-azido-4,6-O-benzylidene-1-O-tert-butyldimethylsilyl-2-deoxy-3-O-(2-naphthalenylmethyl)-D-glucopyranoside (1448013-28-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 °C / Inert atmosphere; Molecular sieve

1.2: 2 h / 0 °C / Inert atmosphere; Molecular sieve

2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.202000923

Reference yield:

benzaldehyde (100-52-7) → 2-azido-4,6-O-benzylidene-1-O-tert-butyldimethylsilyl-2-deoxy-3-O-(2-naphthalenylmethyl)-D-glucopyranoside (1448013-28-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 °C / Inert atmosphere; Molecular sieve

1.2: 2 h / 0 °C / Inert atmosphere; Molecular sieve

2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.202000923

upstream raw materials:

2-azido-4,6-O-benzylidene-2-deoxyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside

2-bromomethylnaphthyl bromide

benzaldehyde

Downstream raw materials:

2-N-acetyl-6-O-allyl-3,4-di-O-benzyl-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-O-levulinoyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

2-N-acetyl-3,4-di-O-benzyl-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate

2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-((N,N,-diisopropylamino)-2-cyanoethylphosphite)-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate