1,2-O-ethylidene-3,4,6-tri-O-[(n-methyl-N-benzyloxycarbamoyl)methyl]-α-D-galactopyranose

Base Information

• Chemical Name: 1,2-O-ethylidene-3,4,6-tri-O-[(n-methyl-N-benzyloxycarbamoyl)methyl]-α-D-galactopyranose
• CAS No.: 1383567-45-0
• Molecular Formula: C₃₈H₄₇N₃O₁₂
• Molecular Weight: 737.804
• Mol file: 1383567-45-0.mol

Synonyms:

Chemical Property of 1,2-O-ethylidene-3,4,6-tri-O-[(n-methyl-N-benzyloxycarbamoyl)methyl]-α-D-galactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-O-ethylidene-3,4,6-tri-O-[(n-methyl-N-benzyloxycarbamoyl)methyl]-α-D-galactopyranose

There total 5 articles about 1,2-O-ethylidene-3,4,6-tri-O-[(n-methyl-N-benzyloxycarbamoyl)methyl]-α-D-galactopyranose 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:

3,4,6-tri-O-acetyl-1,2-O-ethylidene-α-D-galactopyranose (37679-97-3,38081-36-6,38081-37-7,56687-80-0,56687-81-1,83289-92-3,83289-94-5,83289-95-6,83289-98-9,101144-01-8,101144-02-9,112346-26-6) → 1,2-O-ethylidene-3,4,6-tri-O-[(n-methyl-N-benzyloxycarbamoyl)methyl]-α-D-galactopyranose (1383567-45-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: methanol; sodium / 0 - 20 °C

1.2: Dowex_.(R). (H⁺, 50WX₂-100)

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

2.2: 50 °C

3.1: ozone; sodium hydroxide / dichloromethane / -78 °C

4.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C

4.2: Dowex_.(R). (H⁺, 50WX₂-100) / pH 2

5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; N,N-dimethyl-formamide / 2 h / 20 °C

With methanol; lithium hydroxide monohydrate; sodium; sodium hydride; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 2.2: Williamson ether synthesis;

DOI:10.1016/j.jinorgbio.2012.02.030

Reference yield:

1,2-O-ethylidene-3,4,6-tri-O-allyl-α-D-galactopyranose (1383567-41-6) → 1,2-O-ethylidene-3,4,6-tri-O-[(n-methyl-N-benzyloxycarbamoyl)methyl]-α-D-galactopyranose (1383567-45-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ozone; sodium hydroxide / dichloromethane / -78 °C

2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C

2.2: Dowex_.(R). (H⁺, 50WX₂-100) / pH 2

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; N,N-dimethyl-formamide / 2 h / 20 °C

With lithium hydroxide monohydrate; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.jinorgbio.2012.02.030

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 1,2-O-ethylidene-3,4,6-tri-O-[(n-methyl-N-benzyloxycarbamoyl)methyl]-α-D-galactopyranose (1383567-45-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium tetrahydroborate; tetra-(n-butyl)ammonium iodide / acetonitrile / 20 °C

1.2: 0 °C

2.1: methanol; sodium / 0 - 20 °C

2.2: Dowex_.(R). (H⁺, 50WX₂-100)

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

3.2: 50 °C

4.1: ozone; sodium hydroxide / dichloromethane / -78 °C

5.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C

5.2: Dowex_.(R). (H⁺, 50WX₂-100) / pH 2

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; N,N-dimethyl-formamide / 2 h / 20 °C

With methanol; sodium tetrahydroborate; lithium hydroxide monohydrate; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; 3.2: Williamson ether synthesis;

DOI:10.1016/j.jinorgbio.2012.02.030

upstream raw materials:

1,2-O-ethylidene-3,4,6-tri-O-allyl-α-D-galactopyranose

1,2-O-ethylidene-3,4,6-tri-O-(2-oxo-2-methoxy-ethyl)-α-D-galactopyranose

1,2-O-ethylidene-α-D-galactopyranose

3,4,6-tri-O-acetyl-1,2-O-ethylidene-α-D-galactopyranose