methyl 4,6-O-benzilidene-3-deoxy-3-(2-hydroxyethyl)amino-α-D-altropyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzilidene-3-deoxy-3-(2-hydroxyethyl)amino-α-D-altropyranoside
• CAS No.: 1417817-56-1
• Molecular Formula: C₁₆H₂₃NO₆
• Molecular Weight: 325.362
• Mol file: 1417817-56-1.mol

Synonyms:methyl 4,6-O-benzilidene-3-deoxy-3-(2-hydroxyethyl)amino-α-D-altropyranoside

Chemical Property of methyl 4,6-O-benzilidene-3-deoxy-3-(2-hydroxyethyl)amino-α-D-altropyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzilidene-3-deoxy-3-(2-hydroxyethyl)amino-α-D-altropyranoside

There total 2 articles about methyl 4,6-O-benzilidene-3-deoxy-3-(2-hydroxyethyl)amino-α-D-altropyranoside 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: 79.0%

ethanolamine (141-43-5) + methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside (3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2,2880-96-8) → methyl 4,6-O-benzilidene-3-deoxy-3-(2-hydroxyethyl)amino-α-D-altropyranoside (1417817-56-1)

Guidance literature:

at 140 ℃; for 5h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.carres.2012.10.020

Reference yield:

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 4,6-O-benzilidene-3-deoxy-3-(2-hydroxyethyl)amino-α-D-altropyranoside (1417817-56-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h

1.2: 2 h / 20 °C

2.1: 5 h / 140 °C / Inert atmosphere

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2012.10.020

Reference yield: 22.0%

tetraethylene glycol di(p-toluenesulfonate) (37860-51-8) + methyl 4,6-O-benzilidene-3-deoxy-3-(2-hydroxyethyl)amino-α-D-altropyranoside (1417817-56-1) → methyl 4,6-O-benzilydene-2,3-dideoxy-α-D-altropyranosido-[2,3-l]-1,4,7,10,13-pentaoxa-16-azacyclopentadecane (1417817-61-8)

Guidance literature:

methyl 4,6-O-benzilidene-3-deoxy-3-(2-hydroxyethyl)amino-α-D-altropyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 80 ℃; for 4h; Inert atmosphere;

tetraethylene glycol di(p-toluenesulfonate); In N,N-dimethyl-formamide; at 80 ℃; for 50h; Inert atmosphere;

DOI:10.1016/j.carres.2012.10.020

upstream raw materials:

ethanolamine

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

Downstream raw materials:

methyl 4,6-O-benzilydene-2,3-dideoxy-α-D-altropyranosido-[2,3-l]-1,4,7,10-tetraoxa-13-azacyclopentadecane

methyl 4,6-O-benzilydene-2,3-dideoxy-α-D-altropyranosido-[2,3-l]-1,4,7,10,13-pentaoxa-16-azacyclopentadecane