ethyl (4S,5R,6R,2E)-6-[(R)-3'-benzy-4'-[(tert-butyldimethylsilyloxy)methyl]-2'-oxooxazolidin-4'-yl]-5-(benzyloxy)-4,6-(isopropylidenedioxy)hex-2-enoate

Base Information

• Chemical Name: ethyl (4S,5R,6R,2E)-6-[(R)-3'-benzy-4'-[(tert-butyldimethylsilyloxy)methyl]-2'-oxooxazolidin-4'-yl]-5-(benzyloxy)-4,6-(isopropylidenedioxy)hex-2-enoate
• CAS No.: 1258426-90-2
• Molecular Formula: C₃₅H₄₉NO₈Si
• Molecular Weight: 639.861

Synonyms:ethyl (4S,5R,6R,2E)-6-[(R)-3'-benzy-4'-[(tert-butyldimethylsilyloxy)methyl]-2'-oxooxazolidin-4'-yl]-5-(benzyloxy)-4,6-(isopropylidenedioxy)hex-2-enoate

Chemical Property of ethyl (4S,5R,6R,2E)-6-[(R)-3'-benzy-4'-[(tert-butyldimethylsilyloxy)methyl]-2'-oxooxazolidin-4'-yl]-5-(benzyloxy)-4,6-(isopropylidenedioxy)hex-2-enoate

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Technology Process of ethyl (4S,5R,6R,2E)-6-[(R)-3'-benzy-4'-[(tert-butyldimethylsilyloxy)methyl]-2'-oxooxazolidin-4'-yl]-5-(benzyloxy)-4,6-(isopropylidenedioxy)hex-2-enoate

There total 1 articles about ethyl (4S,5R,6R,2E)-6-[(R)-3'-benzy-4'-[(tert-butyldimethylsilyloxy)methyl]-2'-oxooxazolidin-4'-yl]-5-(benzyloxy)-4,6-(isopropylidenedioxy)hex-2-enoate 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: 94.0%

ethyl (4S,5R,6R,2E)-6-[(S)-3'-benzy-4'-(hydroxymethyl)-2'-oxooxazolidin-4'-yl]-5-(benzyloxy)-4,6-(isopropylidenedioxy)hex-2-enoate (1258426-89-9) + t-butyldimethylsiyl triflate (69739-34-0) → ethyl (4S,5R,6R,2E)-6-[(R)-3'-benzy-4'-[(tert-butyldimethylsilyloxy)methyl]-2'-oxooxazolidin-4'-yl]-5-(benzyloxy)-4,6-(isopropylidenedioxy)hex-2-enoate (1258426-90-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1016/j.carres.2010.09.016

Reference yield: 35.0%

ethyl (4S,5R,6R,2E)-6-[(R)-3'-benzy-4'-[(tert-butyldimethylsilyloxy)methyl]-2'-oxooxazolidin-4'-yl]-5-(benzyloxy)-4,6-(isopropylidenedioxy)hex-2-enoate (1258426-90-2) → C33H45NO7Si (1258426-91-3) + (4R)-3-benzyl-4-[(1'R,2'R,3'S,4'E)-2'-(benzyloxy)-6'-hydroxy-1',3'-(isopropylidenedioxy)hex-4'-enyl]-4-[(tert-butyldimethylsilyloxy)methyl]oxazolidin-2-one (1258426-92-4)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 0.5h;

DOI:10.1016/j.carres.2010.09.016

upstream raw materials:

ethyl (4S,5R,6R,2E)-6-[(S)-3'-benzy-4'-(hydroxymethyl)-2'-oxooxazolidin-4'-yl]-5-(benzyloxy)-4,6-(isopropylidenedioxy)hex-2-enoate

t-butyldimethylsiyl triflate

Downstream raw materials:

C₃₃H₄₅NO₇Si

(4R)-3-benzyl-4-[(1'R,2'R,3'S,4'E)-2'-(benzyloxy)-6'-hydroxy-1',3'-(isopropylidenedioxy)hex-4'-enyl]-4-[(tert-butyldimethylsilyloxy)methyl]oxazolidin-2-one

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