2-benzylthio-4,5-dihydro-(1',4',6'-tri-O-benzyl-2',3'-dideoxy-β-D-fructofuranoso)[2,3-d]-oxazole

Base Information

• Chemical Name: 2-benzylthio-4,5-dihydro-(1',4',6'-tri-O-benzyl-2',3'-dideoxy-β-D-fructofuranoso)[2,3-d]-oxazole
• CAS No.: 343921-85-7
• Molecular Formula: C₃₅H₃₅NO₅S
• Molecular Weight: 581.733

Synonyms:2-benzylthio-4,5-dihydro-(1',4',6'-tri-O-benzyl-2',3'-dideoxy-β-D-fructofuranoso)[2,3-d]-oxazole

Chemical Property of 2-benzylthio-4,5-dihydro-(1',4',6'-tri-O-benzyl-2',3'-dideoxy-β-D-fructofuranoso)[2,3-d]-oxazole

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Technology Process of 2-benzylthio-4,5-dihydro-(1',4',6'-tri-O-benzyl-2',3'-dideoxy-β-D-fructofuranoso)[2,3-d]-oxazole

There total 2 articles about 2-benzylthio-4,5-dihydro-(1',4',6'-tri-O-benzyl-2',3'-dideoxy-β-D-fructofuranoso)[2,3-d]-oxazole 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: 64.0%

benzyl bromide (100-39-0) + 1-O-benzyl-2-N,3-O-thiocarbonyl-β-D-fructofuranosylamine (575472-02-5) → 2-benzylthio-4,5-dihydro-(1',4',6'-tri-O-benzyl-2',3'-dideoxy-β-D-fructofuranoso)[2,3-d]-oxazole (343921-85-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.tet.2004.01.032

Reference yield:

1-O-benzyl-D-fructose → 2-benzylthio-4,5-dihydro-(1',4',6'-tri-O-benzyl-2',3'-dideoxy-β-D-fructofuranoso)[2,3-d]-oxazole (343921-85-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 37 percent HCl / H₂O / 20 - 55 °C

2: NaH / dimethylformamide / 20 °C

With hydrogenchloride; sodium hydride; In water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)00357-4

Reference yield: 57.0%

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) + 2-benzylthio-4,5-dihydro-(1',4',6'-tri-O-benzyl-2',3'-dideoxy-β-D-fructofuranoso)[2,3-d]-oxazole (343921-85-7) → O2,O3'-anhydro-3-(1',4',6'-tri-O-benzyl-β-D-fructofuranosyl)-2,4-quinazolinedione (343921-91-5)

Guidance literature:

With 3 A molecular sieve; camphor-10-sulfonic acid; In ethanol; for 24h; Heating;

DOI:10.1016/S0040-4039(01)00357-4

upstream raw materials:

benzyl bromide

1-O-benzyl-2-N,3-O-thiocarbonyl-β-D-fructofuranosylamine

Downstream raw materials:

O²,O^3'-anhydro-3-(1',4',6'-tri-O-benzyl-β-D-fructofuranosyl)-2,4-quinazolinedione

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