methyl (3S,5R,2'R,4'S,5'R)-2-N-benzyl-3-(5-tert-butyldimethylsilyloxy-2-methyl-1,3-dioxan-4-yl)isoxazolidine-5-carboxylate

Base Information

• Chemical Name: methyl (3S,5R,2'R,4'S,5'R)-2-N-benzyl-3-(5-tert-butyldimethylsilyloxy-2-methyl-1,3-dioxan-4-yl)isoxazolidine-5-carboxylate
• CAS No.: 404346-81-2
• Molecular Formula: C₂₃H₃₇NO₆Si
• Molecular Weight: 451.635

Synonyms:methyl (3S,5R,2'R,4'S,5'R)-2-N-benzyl-3-(5-tert-butyldimethylsilyloxy-2-methyl-1,3-dioxan-4-yl)isoxazolidine-5-carboxylate

Chemical Property of methyl (3S,5R,2'R,4'S,5'R)-2-N-benzyl-3-(5-tert-butyldimethylsilyloxy-2-methyl-1,3-dioxan-4-yl)isoxazolidine-5-carboxylate

Chemical Property:

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• Pictogram(s):  
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MSDS Files:

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Technology Process of methyl (3S,5R,2'R,4'S,5'R)-2-N-benzyl-3-(5-tert-butyldimethylsilyloxy-2-methyl-1,3-dioxan-4-yl)isoxazolidine-5-carboxylate

There total 2 articles about methyl (3S,5R,2'R,4'S,5'R)-2-N-benzyl-3-(5-tert-butyldimethylsilyloxy-2-methyl-1,3-dioxan-4-yl)isoxazolidine-5-carboxylate 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%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + (Z)-N-[1-deoxy-2,4-O-ethylidene-O3-(tert-butyldimethylsilyl)-D-erythro-1-ylidene]benzylamine N-oxide (221351-76-4,404346-79-8) → methyl (3S,5R,2'R,4'S,5'R)-2-N-benzyl-3-(5-tert-butyldimethylsilyloxy-2-methyl-1,3-dioxan-4-yl)isoxazolidine-5-carboxylate (404346-81-2)

Guidance literature:

In toluene; at 110 ℃; for 4h;

DOI:10.1055/s-2001-18783

Reference yield: 78.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + (Z)-N-[1-deoxy-2,4-O-ethylidene-O3-(tert-butyldimethylsilyl)-D-erythro-1-ylidene]benzylamine N-oxide (221351-76-4,404346-79-8) → methyl (3S,5R,2'R,4'S,5'R)-2-N-benzyl-3-(5-tert-butyldimethylsilyloxy-2-methyl-1,3-dioxan-4-yl)isoxazolidine-5-carboxylate (404346-81-2) + (3S,5S)-2-Benzyl-3-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-[1,3]dioxan-4-yl]-isoxazolidine-5-carboxylic acid methyl ester + (3R,5R)-2-Benzyl-3-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-[1,3]dioxan-4-yl]-isoxazolidine-5-carboxylic acid methyl ester + (3R,5S)-2-Benzyl-3-[(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-[1,3]dioxan-4-yl]-isoxazolidine-5-carboxylic acid methyl ester

Guidance literature:

In toluene; at 110 ℃; for 4h;

DOI:10.1055/s-2001-18782

Reference yield: 98.0%

methyl (3S,5R,2'R,4'S,5'R)-2-N-benzyl-3-(5-tert-butyldimethylsilyloxy-2-methyl-1,3-dioxan-4-yl)isoxazolidine-5-carboxylate (404346-81-2) → (3S,5R,2'R,4'S,5'R)-2-N-benzyl-3-(5-tert-butyldimethylsilyloxy-2-methyl-1,3-dioxan-4-yl)-5-hydroxymethylisoxazolidine

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -10 ℃; for 1.5h;

DOI:10.1055/s-2001-18783

upstream raw materials:

acrylic acid methyl ester

(Z)-N-[1-deoxy-2,4-O-ethylidene-O³-(tert-butyldimethylsilyl)-D-erythro-1-ylidene]benzylamine N-oxide

Downstream raw materials:

(1S,2R,6R,7aS)-pyrrolizidine-1,2,6-triol

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