N-[2-(3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)propyl]phthalimide

Base Information

• Chemical Name: N-[2-(3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)propyl]phthalimide
• CAS No.: 282724-65-6
• Molecular Formula: C₃₈H₃₉NO₈
• Molecular Weight: 637.73
• Mol file: 282724-65-6.mol

Synonyms:N-[2-(3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)propyl]phthalimide

Chemical Property of N-[2-(3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)propyl]phthalimide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[2-(3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)propyl]phthalimide

There total 2 articles about N-[2-(3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)propyl]phthalimide 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:

N-(3-hydroxypropyl)phthalimide (883-44-3) + glucal epoxide (1011723-04-8) → N-[2-(3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)propyl]phthalimide (282724-65-6)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 17h;

DOI:10.1039/a908512b

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → N-[2-(3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)propyl]phthalimide (282724-65-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 4 Angstroem molecular sieves / CH₂Cl₂; acetone / 1 h / 0 °C

2: zinc chloride / tetrahydrofuran; diethyl ether / 17 h / -78 - 20 °C

With 4 A molecular sieve; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; 1: Epoxidation / 2: Etherification;

DOI:10.1039/a908512b

Reference yield: 67.0%

N-[2-(3,4,6-tri-O-benzyl-β-D-glucopyranosyloxy)propyl]phthalimide (282724-65-6) → 3-aminopropyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside (282724-71-4)

Guidance literature:

With hydrazine hydrate; In methanol; at 20 ℃;

DOI:10.1039/a908512b

upstream raw materials:

N-(3-hydroxypropyl)phthalimide

glucal epoxide

3,4,6-tri-O-benzyl-D-glucal

Downstream raw materials:

3-aminopropyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside

3-(N-methylamino)propyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside

N-[3-((2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-propyl]-formamide