allyl 2-deoxy-4,6-O-p-methoxybenzylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 2-deoxy-4,6-O-p-methoxybenzylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
• CAS No.: 188583-15-5
• Molecular Formula: C₂₀H₂₄Cl₃NO₈
• Molecular Weight: 512.771
• Mol file: 188583-15-5.mol

Synonyms:allyl 2-deoxy-4,6-O-p-methoxybenzylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Chemical Property of allyl 2-deoxy-4,6-O-p-methoxybenzylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-deoxy-4,6-O-p-methoxybenzylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

There total 1 articles about allyl 2-deoxy-4,6-O-p-methoxybenzylidene-2-(2,2,2-trichloroethoxycarbonylamino)-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: 94.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + allyl-2-N-Troc-2-deoxy-α-D-glucopyranoside (188583-14-4) → allyl 2-deoxy-4,6-O-p-methoxybenzylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (188583-15-5)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 18h; Ambient temperature;

DOI:10.1248/cpb.45.312

Reference yield: 75.0%

allyl 2-deoxy-4,6-O-p-methoxybenzylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (188583-15-5) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → allyl 2-deoxy-4,6-O-p-methoxybenzylidene-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (188583-16-6)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1248/cpb.45.312

Reference yield:

allyl 2-deoxy-4,6-O-p-methoxybenzylidene-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (188583-15-5) → 4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (188583-18-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / 4-dimethylaminopyridine, pyridine / CH₂Cl₂ / 20 h / Ambient temperature

2: 94 percent / 68percent aq. AcOH / 5 h / Ambient temperature

3: 98 percent / CF₃SO₃H / CH₂Cl₂; cyclohexane / 20 h / Ambient temperature

4: 1.) 1,5-cyclooctadienebis(methyldiphenylphosphine)iridium hexafluorophosphate, 2.) I₂, pyridine, H₂O / 1.) THF, 50 deg C, 2 h, 2.) THF, RT, 30 min

With pyridine; dmap; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trifluorormethanesulfonic acid; water; iodine; acetic acid; In dichloromethane; cyclohexane;

DOI:10.1248/cpb.45.312

upstream raw materials:

p-Anisaldehyde dimethyl acetal

allyl-2-N-Troc-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

allyl 2-deoxy-4,6-O-p-methoxybenzylidene-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

allyl 4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

N-tetradecanoyl-O-[4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester