t-butyl (3S)-2-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)-3-isoxazolidinecarboxylate

Base Information

Chemical Name:t-butyl (3S)-2-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)-3-isoxazolidinecarboxylate
CAS No.:78266-73-6
Molecular Formula:C₂₀H₃₃NO₈
Molecular Weight:415.484
Hs Code.:

Synonyms:t-butyl (3S)-2-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)-3-isoxazolidinecarboxylate

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Chemical Property of t-butyl (3S)-2-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)-3-isoxazolidinecarboxylate

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Technology Process of t-butyl (3S)-2-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)-3-isoxazolidinecarboxylate

There total 1 articles about t-butyl (3S)-2-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)-3-isoxazolidinecarboxylate 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: 43.0%

: 35023-80-4
2,3:5,6-di-O-isopropylidene-D-mannose oxime

: 74-85-1
ethene

: 7633-32-1
tert-butyl glyoxylate

: t-butyl (3R)-2-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)-3-isoxazolidinecarboxylate

: 78266-73-6
t-butyl (3S)-2-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)-3-isoxazolidinecarboxylate

Guidance literature:: In chloroform; at 75 ℃; for 17h; under 48753.9 Torr; Yield given. Title compound not separated from byproducts;
DOI:10.1039/c39810000097

Reference yield:

: 78266-73-6
t-butyl (3S)-2-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)-3-isoxazolidinecarboxylate

: 47307-26-6,149967-07-7
(S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / 36percent HCl / H₂O; methanol / 6 h / Ambient temperature

2: 1.75 g / hydrogen / 5percent Rh/C / ethanol / 20 h / Ambient temperature

3: 79 percent / 1 M NaHCO₃, 1 M Na₂CO₃ / CHCl₃ / 5 h / Ambient temperature

4: 84 percent / KMnO₄ / acetone; acetic acid / 3.5 h / Ambient temperature

With hydrogenchloride; potassium permanganate; hydrogen; sodium hydrogencarbonate; sodium carbonate; Rh on carbon; In methanol; ethanol; chloroform; water; acetic acid; acetone;
DOI:10.1002/hlca.19830660424

Reference yield:

: 78266-73-6
t-butyl (3S)-2-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)-3-isoxazolidinecarboxylate

: 25456-85-3
(S)-N-benzyloxycarbonylaspargine t-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / 36percent HCl / H₂O; methanol / 6 h / Ambient temperature

2: 1.75 g / hydrogen / 5percent Rh/C / ethanol / 20 h / Ambient temperature

3: 79 percent / 1 M NaHCO₃, 1 M Na₂CO₃ / CHCl₃ / 5 h / Ambient temperature

4: 84 percent / KMnO₄ / acetone; acetic acid / 3.5 h / Ambient temperature

5: 1.) N-methylmorpholine, isobutyl chloroformate; 2.) NH₃ / 1.) THF, 7 min, -20 deg C; 2.) water, 2 h, -15 -> 10 deg C

With 4-methyl-morpholine; hydrogenchloride; potassium permanganate; ammonia; hydrogen; sodium hydrogencarbonate; sodium carbonate; isobutyl chloroformate; Rh on carbon; In methanol; ethanol; chloroform; water; acetic acid; acetone;
DOI:10.1002/hlca.19830660424