Methyl N-benzyl-5-deoxy-5-(hydroxyamino)-2,3-O-isopropylidene-5-(2-thiazolyl)-β-D-allo-1,4-pentofuranoside

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Chemical Name:Methyl N-benzyl-5-deoxy-5-(hydroxyamino)-2,3-O-isopropylidene-5-(2-thiazolyl)-β-D-allo-1,4-pentofuranoside
CAS No.:173382-30-4
Molecular Formula:C₁₉H₂₄N₂O₅S
Molecular Weight:392.476
Hs Code.:

Synonyms:Methyl N-benzyl-5-deoxy-5-(hydroxyamino)-2,3-O-isopropylidene-5-(2-thiazolyl)-β-D-allo-1,4-pentofuranoside

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Chemical Property of Methyl N-benzyl-5-deoxy-5-(hydroxyamino)-2,3-O-isopropylidene-5-(2-thiazolyl)-β-D-allo-1,4-pentofuranoside

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Technology Process of Methyl N-benzyl-5-deoxy-5-(hydroxyamino)-2,3-O-isopropylidene-5-(2-thiazolyl)-β-D-allo-1,4-pentofuranoside

There total 2 articles about Methyl N-benzyl-5-deoxy-5-(hydroxyamino)-2,3-O-isopropylidene-5-(2-thiazolyl)-β-D-allo-1,4-pentofuranoside 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: 65.0%

: 3034-53-5,215777-74-5
2-bromo-1,3-thiazole

: 161614-79-5,191997-34-9
(Z)-N-(5-deoxy-2,3-O-isopropylidene-1-O-methyl-β-D-ribo-1,4-furanose-5-ylidene)benzylamine N-oxide

: 173382-30-4
Methyl N-benzyl-5-deoxy-5-(hydroxyamino)-2,3-O-isopropylidene-5-(2-thiazolyl)-β-D-allo-1,4-pentofuranoside

: 173382-29-1
Methyl N-benzyl-5-deoxy-5-(hydroxyamino)-2,3-O-isopropylidene-5-(2-thiazolyl)-α-L-talo-1,4-pentofuranoside

Guidance literature:: In tetrahydrofuran; diethyl ether; hexane; Yields of byproduct given; 1.) -78 deg C, 15 min, 2.) -80 deg C, 15 min;

Reference yield: 59.0%

: 3034-53-5,215777-74-5
2-bromo-1,3-thiazole

: 161614-79-5,191997-34-9
(Z)-N-(5-deoxy-2,3-O-isopropylidene-1-O-methyl-β-D-ribo-1,4-furanose-5-ylidene)benzylamine N-oxide

: 173382-30-4
Methyl N-benzyl-5-deoxy-5-(hydroxyamino)-2,3-O-isopropylidene-5-(2-thiazolyl)-β-D-allo-1,4-pentofuranoside

: 173382-29-1
Methyl N-benzyl-5-deoxy-5-(hydroxyamino)-2,3-O-isopropylidene-5-(2-thiazolyl)-α-L-talo-1,4-pentofuranoside

Guidance literature:: With n-butyllithium; diethylaluminium chloride; In diethyl ether; hexane; Yields of byproduct given; 1.) -78 deg C, 15 min, 2.) -80 deg C, 30 min;

Reference yield:

: 173382-30-4
Methyl N-benzyl-5-deoxy-5-(hydroxyamino)-2,3-O-isopropylidene-5-(2-thiazolyl)-β-D-allo-1,4-pentofuranoside

: 5-(Benzyloxycarbonylamino)-5-deoxy-2,3-O-isopropylidene-1-O-methyl-β-D-allo-hexodialdo-1,4-furanose

Guidance literature:: Multi-step reaction with 3 steps

1: 20percent aq. TiCl₃ / methanol / 0.25 h / Ambient temperature

2: 7percent aq. NaHCO₃ / dioxane / 0.33 h / 0 °C

With titanium(III) chloride; sodium hydrogencarbonate; In 1,4-dioxane; methanol;