methyl 2,3,4-trideoxy-2-phthalimido-6-O-trityl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,4-trideoxy-2-phthalimido-6-O-trityl-α-D-glucopyranoside
• CAS No.: 99239-06-2
• Molecular Formula: C₃₄H₃₁NO₅
• Molecular Weight: 533.624
• Mol file: 99239-06-2.mol

Synonyms:methyl 2,3,4-trideoxy-2-phthalimido-6-O-trityl-α-D-glucopyranoside

Chemical Property of methyl 2,3,4-trideoxy-2-phthalimido-6-O-trityl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4-trideoxy-2-phthalimido-6-O-trityl-α-D-glucopyranoside

There total 6 articles about methyl 2,3,4-trideoxy-2-phthalimido-6-O-trityl-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: 78.0%

N-ethoxycarbonylphthalimide (22509-74-6) + methyl 2-amino-2,3,4-trideoxy-6-O-trityl-α-D-glucopyranoside (99239-05-1) → methyl 2,3,4-trideoxy-2-phthalimido-6-O-trityl-α-D-glucopyranoside (99239-06-2)

Guidance literature:

With triethylamine; In dichloromethane; 1.) 2 h, room temp., 2.) overnight, room temp., 3.) 5 h, reflux;

DOI:10.1016/0008-6215(86)85023-6

Reference yield:

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) → methyl 2,3,4-trideoxy-2-phthalimido-6-O-trityl-α-D-glucopyranoside (99239-06-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) HCl / 1.) 6 h, reflux, 2.) pyridine, 5.5 h, room temp., 2 h, 100 deg C

2: 81 percent / pyridine / Ambient temperature

3: 67 percent / Zn, NaI / dimethylformamide / 5.5 h / 95 °C

4: 3.74 g / H₂ / 10percent Pd-C / ethyl acetate; acetic acid / 6 h / 760 Torr / Ambient temperature

5: 78 percent / Et₃N / CH₂Cl₂ / 1.) 2 h, room temp., 2.) overnight, room temp., 3.) 5 h, reflux

With hydrogenchloride; hydrogen; triethylamine; sodium iodide; zinc; palladium on activated charcoal; In pyridine; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(86)85023-6

Reference yield:

trityl chloride (76-83-5) → methyl 2,3,4-trideoxy-2-phthalimido-6-O-trityl-α-D-glucopyranoside (99239-06-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) HCl / 1.) 6 h, reflux, 2.) pyridine, 5.5 h, room temp., 2 h, 100 deg C

2: 81 percent / pyridine / Ambient temperature

3: 67 percent / Zn, NaI / dimethylformamide / 5.5 h / 95 °C

4: 3.74 g / H₂ / 10percent Pd-C / ethyl acetate; acetic acid / 6 h / 760 Torr / Ambient temperature

5: 78 percent / Et₃N / CH₂Cl₂ / 1.) 2 h, room temp., 2.) overnight, room temp., 3.) 5 h, reflux

With hydrogenchloride; hydrogen; triethylamine; sodium iodide; zinc; palladium on activated charcoal; In pyridine; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(86)85023-6

upstream raw materials:

N-ethoxycarbonylphthalimide

methyl 2-amino-2,3,4-trideoxy-6-O-trityl-α-D-glucopyranoside

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

trityl chloride

Downstream raw materials:

methyl 2,6-bis(benzyloxycarbonylamino)-2,3,4,6,7-pentadeoxy-α-D-ribo-heptopyranoside

methyl 2,6-bis(benzyloxycarbonylamino)-2,3,4,6,7-pentadeoxy-β-L-lyxo-heptopyranoside

methyl 6-O-benzoyl-2,3,4,7-tetradeoxy-2-phthalimido-α-D-ribo-heptopyranoside

methyl 2-benzyloxycarbonylamino-2,3,4,7-tetradeoxy-6-O-(methylsulfonyl)-α-D-ribo-heptopyranoside