diethyl (2S,3aS,4S,5S,6S)-4,5-dibenzyloxy-6-[(1S)-1,2-dibenzyloxyethyl]hexahydropyrrolo[1,2-b]isoxazole-2-methylphosphonate

Base Information

• Chemical Name: diethyl (2S,3aS,4S,5S,6S)-4,5-dibenzyloxy-6-[(1S)-1,2-dibenzyloxyethyl]hexahydropyrrolo[1,2-b]isoxazole-2-methylphosphonate
• CAS No.: 912954-97-3
• Molecular Formula: C₄₁H₅₀NO₈P
• Molecular Weight: 715.824
• Mol file: 912954-97-3.mol

Synonyms:diethyl (2S,3aS,4S,5S,6S)-4,5-dibenzyloxy-6-[(1S)-1,2-dibenzyloxyethyl]hexahydropyrrolo[1,2-b]isoxazole-2-methylphosphonate

Chemical Property of diethyl (2S,3aS,4S,5S,6S)-4,5-dibenzyloxy-6-[(1S)-1,2-dibenzyloxyethyl]hexahydropyrrolo[1,2-b]isoxazole-2-methylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl (2S,3aS,4S,5S,6S)-4,5-dibenzyloxy-6-[(1S)-1,2-dibenzyloxyethyl]hexahydropyrrolo[1,2-b]isoxazole-2-methylphosphonate

There total 2 articles about diethyl (2S,3aS,4S,5S,6S)-4,5-dibenzyloxy-6-[(1S)-1,2-dibenzyloxyethyl]hexahydropyrrolo[1,2-b]isoxazole-2-methylphosphonate 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: 88.0%

(2S,3S,4S)-3,4-bis(benzyloxy)-2-((S)-1,2-bis(benzyloxy)ethyl)-3,4-dihydro-2H-pyrrole-1-oxide (912954-96-2) + Diethyl allylphosphonate (1067-87-4) → diethyl (2S,3aS,4S,5S,6S)-4,5-dibenzyloxy-6-[(1S)-1,2-dibenzyloxyethyl]hexahydropyrrolo[1,2-b]isoxazole-2-methylphosphonate (912954-97-3)

Guidance literature:

In 1,1,2,2-tetrachloroethylene; at 50 ℃;

DOI:10.1021/jo061130e

Reference yield:

2,3,5,6-tetra-O-benzyl-4-O-methanesulfonylaldehydo-D-glucose → diethyl (2S,3aS,4S,5S,6S)-4,5-dibenzyloxy-6-[(1S)-1,2-dibenzyloxyethyl]hexahydropyrrolo[1,2-b]isoxazole-2-methylphosphonate (912954-97-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / tetrabutylammonium triphenyldifluorosiliconate / tetrahydrofuran / 0.75 h / Heating

2: 88 percent / tetrachloroethene / 50 °C

With tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; 1,1,2,2-tetrachloroethylene;

DOI:10.1021/jo061130e

Reference yield: 62.0%

diethyl (2S,3aS,4S,5S,6S)-4,5-dibenzyloxy-6-[(1S)-1,2-dibenzyloxyethyl]hexahydropyrrolo[1,2-b]isoxazole-2-methylphosphonate (912954-97-3) → (1S)-2,3,5,6-tetra-O-benzyl-1,4-dideoxy-1-C-[(2S)-3-diethoxyphosphoryl-2-hydroxypropyl]-1,4-imino-D-galactitol (912954-98-4)

Guidance literature:

With copper diacetate; acetic acid; zinc; at 70 ℃; for 1h;

DOI:10.1021/jo061130e

upstream raw materials:

(2S,3S,4S)-3,4-bis(benzyloxy)-2-((S)-1,2-bis(benzyloxy)ethyl)-3,4-dihydro-2H-pyrrole-1-oxide

Diethyl allylphosphonate

Downstream raw materials:

(1S)-2,3,5,6-tetra-O-benzyl-1,4-dideoxy-1-C-[(2S)-3-diethoxyphosphoryl-2-hydroxypropyl]-1,4-imino-D-galactitol