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

Base Information

• Chemical Name: (2S,3S,4S)-3,4-bis(benzyloxy)-2-((S)-1,2-bis(benzyloxy)ethyl)-3,4-dihydro-2H-pyrrole-1-oxide
• CAS No.: 912954-96-2
• Molecular Formula: C₃₄H₃₅NO₅
• Molecular Weight: 537.656

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

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

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

There total 10 articles about (2S,3S,4S)-3,4-bis(benzyloxy)-2-((S)-1,2-bis(benzyloxy)ethyl)-3,4-dihydro-2H-pyrrole-1-oxide 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: 92.0%

methyl 2,3,5,6-tetra-O-benzyl-4-mesyl-D-glucose-oxime (1422008-08-9) → (2S,3S,4S)-3,4-bis(benzyloxy)-2-((S)-1,2-bis(benzyloxy)ethyl)-3,4-dihydro-2H-pyrrole-1-oxide (912954-96-2)

Guidance literature:

With hydroxylamine hydrochloride; sodium hydrogencarbonate; In methanol; water; for 12h; stereoselective reaction; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2012.12.018

Reference yield: 62.0%

methyl 2,3,5,6-tetra-O-benzyl-4-mesyl-D-glucose-O-(tert-butyldimethylsilyl)-oxime → (2S,3S,4S)-3,4-bis(benzyloxy)-2-((S)-1,2-bis(benzyloxy)ethyl)-3,4-dihydro-2H-pyrrole-1-oxide (912954-96-2) + methyl 2,3,5,6-tetra-O-benzyl-4-mesyl-D-glucose-oxime (1422008-08-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.166667h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.12.018

Reference yield: 51.0%

2,3,5,6-tetra-O-benzyl-4-O-methanesulfonylaldehydo-D-glucose → (2S,3S,4S)-3,4-bis(benzyloxy)-2-((S)-1,2-bis(benzyloxy)ethyl)-3,4-dihydro-2H-pyrrole-1-oxide (912954-96-2)

Guidance literature:

With tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; for 0.75h; Heating;

DOI:10.1021/jo061130e

upstream raw materials:

2,3,5,6-tetra-O-benzyl-α/β-D-galactofuranose

methyl 2,3,5,6-tetra-O-benzyl-4-mesyl-D-glucose-oxime

D-Galactose

Downstream raw materials:

ethyl (2',3'-O-isopropylideneuridin-5'-yl)(2S,3aS,4S,5S,6S)-4,5-dibenzyloxy-6-[(1S)-1,2-dibenzyloxyethyl]hexahydropyrrolo[1,2-b]isoxazole-2-methylphosphonate

3-((2S,3S,4S,5S)-5-((S)-1,2-bis(benzyloxy)ethyl)-3,4-bis(benzyloxy)-1-hydroxy-pyrrolidin-2-yl)propionic acid ethyl ester

C₅₆H₆₁NO₁₀

methyl 5,6-tetradehydro-5,6,7,10-tetradeoxy-7,10-hydroxylamino-2,3,8,9,11,12-hexa-O-benzyl-D-galacto-β-D-galacto-dodecafuranose

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