ChemicalBook CAS DataBase List 1,5-Anhydro-2,3,4-trideoxy-2-[[(1,1-diMethylethoxy)carbonyl]aMino]-D-erythrohexitol

1,5-Anhydro-2,3,4-trideoxy-2-[[(1,1-diMethylethoxy)carbonyl]aMino]-D-erythrohexitol synthesis

8synthesis methods

Product Name:1,5-Anhydro-2,3,4-trideoxy-2-[[(1,1-diMethylethoxy)carbonyl]aMino]-D-erythrohexitol
CAS Number:603130-12-7
Molecular formula:C11H21NO4
Molecular Weight:231.29

D-erythro-Hex-3-enitol, 1,5-anhydro-2,3,4-trideoxy-2-[[(1,1-dimethylethoxy)carbonyl]amino]-

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1,5-Anhydro-2,3,4-trideoxy-2-[[(1,1-diMethylethoxy)carbonyl]aMino]-D-erythrohexitol

603130-12-7
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Yield:603130-12-7 92%

Reaction Conditions:

with hydrogen;platinum(IV) oxide in ethyl acetate; for 3 h;

Steps:

B.ii

To a well-stirred solution of intermediate Bi. (112 g, 488 mmol) in EA (1.2 L) was added platinum oxide (5 g). The reaction was evacuated twice and back-filled with hydrogen. The reaction proceeded 3 h supplying hydrogen when needed. Upon completion, the reaction mixture was filtered through plug of Celite. The filtrate was concentrated to dryness and the residue was resuspended in diisopropylether (200 mL) and Hept (800 mL). After stirring for 1 h, the slurry was cooled to 0⁰C for one hour, filtered and the solid was washed with Hept and dried in vacuo to yield the title alcohol as a white solid (104 g, 92% yield). ¹H NMR (CDCl₃) δ: 4.25 (br. s, IH); 4.11 (m, IH); 3.60 (dd, J = 3.4, 11.5 Hz, 2H); 3.53 (m, IH); 3.37 (m, 1 H); 3.02 (t, J = 10.7 Hz, IH); 2.10 (m, IH); 1.83 (br. s, IH); 1.62 (m, IH); 1.49 (m, IH); 1.44 (s, 9H); 1.32 (m, IH).

References:

WO2008/152603,2008,A1 Location in patent:Page/Page column 38

D-erythro-Hex-3-enitol, 1,5-anhydro-2,3,4-trideoxy-2-[[(1,1-dimethylethoxy)carbonyl]amino]-6-O-[(1,1-dimethylethyl)dimethylsilyl]-

603130-11-6
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603130-12-7
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D-erythro-Hex-2-enitol, 1,5-anhydro-2,3-dideoxy-

125901-90-8
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603130-12-7
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1,5-Anhydro-2,3-dideoxy-6-O-[(1,1-diMethylethyl)diMethylsilyl]-D-erythro-Hex-2-enitol

132375-36-1
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603130-12-7
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References

(2R,3S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl 3,3,3-trichloropropanimidate

199801-85-9
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603130-12-7
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References