1,2,3,4-tetradeoxy-4-{hydroxy[(1S)-1-phenylbut-3-enyl]amino}-5,6-O-(1-methylethylidene)-D-ribo-hept-1-enitol

Base Information

• Chemical Name: 1,2,3,4-tetradeoxy-4-{hydroxy[(1S)-1-phenylbut-3-enyl]amino}-5,6-O-(1-methylethylidene)-D-ribo-hept-1-enitol
• CAS No.: 845817-23-4
• Molecular Formula: C₂₀H₂₉NO₄
• Molecular Weight: 347.455

Synonyms:1,2,3,4-tetradeoxy-4-{hydroxy[(1S)-1-phenylbut-3-enyl]amino}-5,6-O-(1-methylethylidene)-D-ribo-hept-1-enitol

Chemical Property of 1,2,3,4-tetradeoxy-4-{hydroxy[(1S)-1-phenylbut-3-enyl]amino}-5,6-O-(1-methylethylidene)-D-ribo-hept-1-enitol

Chemical Property:

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Technology Process of 1,2,3,4-tetradeoxy-4-{hydroxy[(1S)-1-phenylbut-3-enyl]amino}-5,6-O-(1-methylethylidene)-D-ribo-hept-1-enitol

There total 1 articles about 1,2,3,4-tetradeoxy-4-{hydroxy[(1S)-1-phenylbut-3-enyl]amino}-5,6-O-(1-methylethylidene)-D-ribo-hept-1-enitol 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: 79.0%

allylmagnesium bromide (2622-05-1) + (3aR,4R,6aR)-tetrahydro-2,2-dimethyl-N-(phenylmethylene)furo[3,4-d]-1,3-dioxol-4-amine N-oxide (444911-56-2) → 1,2,3,4-tetradeoxy-4-{hydroxy[(1R)-1-phenylbut-3-enyl]amino}-5,6-O-(1-methylethylidene)-D-ribo-hept-1-enitol + 1,2,3,4-tetradeoxy-4-{hydroxy[(1S)-1-phenylbut-3-enyl]amino}-5,6-O-(1-methylethylidene)-D-ribo-hept-1-enitol (845817-23-4)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/ol047691e

Reference yield: 93.0%

1,2,3,4-tetradeoxy-4-{hydroxy[(1S)-1-phenylbut-3-enyl]amino}-5,6-O-(1-methylethylidene)-D-ribo-hept-1-enitol (845817-23-4) + acetic anhydride (108-24-7) → 1,2,3,4-tetradeoxy-4-{acetyloxy[(1S)-1-phenylbut-3-enyl]amino}-5,6-O-(1-methylethylidene)-D-ribo-hept-1-enitol (845817-30-3)

Guidance literature:

In tetrahydrofuran; for 1.5h; Heating;

DOI:10.1021/ol047691e

Reference yield: 65.0%

1,2,3,4-tetradeoxy-4-{hydroxy[(1S)-1-phenylbut-3-enyl]amino}-5,6-O-(1-methylethylidene)-D-ribo-hept-1-enitol (845817-23-4) → {(4R,5S)-2,2-dimethyl-5-[(S)-1-(((S)-1-phenylbut-3-en-1-yl)amino)but-3-en-1-yl]-1,3-dioxolan-4-yl}methanol

Guidance literature:

With acetic acid; zinc; In water; at 20 ℃; for 2h;

DOI:10.1002/ejic.201901081

upstream raw materials:

allylmagnesium bromide

(3aR,4R,6aR)-tetrahydro-2,2-dimethyl-N-(phenylmethylene)furo[3,4-d]-1,3-dioxol-4-amine N-oxide

Downstream raw materials:

1,2,3,4-tetradeoxy-4-{acetyloxy[(1S)-1-phenylbut-3-enyl]amino}-5,6-O-(1-methylethylidene)-D-ribo-hept-1-enitol

(3aR,6S,10aS,10bS)-2,2-dimethyl-6-phenyl-3a,6,7,10,10a,10b-hexahydro-4H-[1,3]dioxolo[3,4]pyrrolo[1,2-a]azepine

{(4R,5S)-2,2-dimethyl-5-[(2S,7S)-7-phenyl-2,3,6,7-tetrahydro-1H-azepin-2-yl]-1,3-dioxolan-4-yl}methanol

(2S,7S)-2-[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-phenyl-2,3,6,7-tetrahydro-1H-azepin-1-ol

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