2-O-benzyloxyethyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 2-O-benzyloxyethyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 118638-76-9
• Molecular Formula: C₂₃H₃₁NO₁₀
• Molecular Weight: 481.5
• Mol file: 118638-76-9.mol

Synonyms:2-O-benzyloxyethyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Chemical Property of 2-O-benzyloxyethyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-benzyloxyethyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

There total 9 articles about 2-O-benzyloxyethyl-2-acetamido-3,4,6-tri-O-acetyl-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: 82.0%

2-Benzyloxyethanol (622-08-2,1201808-31-2) + 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) → 2-O-benzyloxyethyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (118638-76-9)

Guidance literature:

With (R)-10-camphorsulfonic acid; In dichloromethane; at 40 ℃; for 3h; Molecular sieve;

DOI:10.1016/j.bmc.2009.12.031

Reference yield:

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → 2-O-benzyloxyethyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (118638-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1: CaSO₄, BF₃*Et₂O / CH₂Cl₂ / 19 h / Ambient temperature

2: p-TsOH*H₂O / CHCl₃ / 6.5 h / Heating

With calcium sulfate; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In dichloromethane; chloroform;

DOI:10.1248/cpb.38.3366

Reference yield:

1-bromo-2-deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranose (63000-69-1) → 2-O-benzyloxyethyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (118638-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1: silver carbonate / dichloromethane / 16 h

2: tetrahydrofuran / 16 h

3: dmap; pyridine / 24 h / 20 °C

With pyridine; dmap; silver carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo402700y

upstream raw materials:

2-Benzyloxyethanol

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose

1-bromo-2-deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranose

Downstream raw materials:

Tetradecanoic acid (4aR,6R,7R,8R,8aS)-6-[2-(diphenoxy-phosphoryloxy)-ethoxy]-2,2-dimethyl-7-tetradecanoylamino-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

2-(diphenylphosphonooxy)ethyl 2-deoxy-3-O-tetradecanoyl-2-tetradecanoylamino-β-D-glucopyranoside

2-benzyloxyethyl 2-deoxy-4,6-O-isopropylidene-3-O-tetradecanoyl-2-tetradecanoylamino-β-D-glucopyranoside

2-benzyloxyethyl 3,4,6-tri-O-acetyl-2-deoxy-2-tetradecanoylamino-β-D-glucopyranoside