N-((1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-hydroxy-2-oxa-bicyclo[3.3.1]non-7-en-5-yl)-acetamide

Base Information

Chemical Name:N-((1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-hydroxy-2-oxa-bicyclo[3.3.1]non-7-en-5-yl)-acetamide
CAS No.:174741-80-1
Molecular Formula:C₂₅H₂₇NO₆
Molecular Weight:437.492
Hs Code.:

Synonyms:N-((1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-hydroxy-2-oxa-bicyclo[3.3.1]non-7-en-5-yl)-acetamide

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Chemical Property of N-((1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-hydroxy-2-oxa-bicyclo[3.3.1]non-7-en-5-yl)-acetamide

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Technology Process of N-((1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-hydroxy-2-oxa-bicyclo[3.3.1]non-7-en-5-yl)-acetamide

There total 5 articles about N-((1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-hydroxy-2-oxa-bicyclo[3.3.1]non-7-en-5-yl)-acetamide 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: 95.0%

: N-{(1R,3R,6R,7S,8R,10S)-7,10-Bis-benzyloxy-4-[1-methoxy-meth-(Z)-ylidene]-2,9-dioxa-tricyclo[4.3.1.0^3,8]dec-6-yl}-acetamide

: 174741-80-1
N-((1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-hydroxy-2-oxa-bicyclo[3.3.1]non-7-en-5-yl)-acetamide

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; at 57 ℃; for 18h;
DOI:10.1021/jo951747o

Reference yield:

: 100-39-0
benzyl bromide

: 174741-80-1
N-((1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-hydroxy-2-oxa-bicyclo[3.3.1]non-7-en-5-yl)-acetamide

Guidance literature:: Multi-step reaction with 3 steps

1: NaH, TBAI / tetrahydrofuran; dimethylformamide; paraffin / 24 h

2: 62 percent / n-BuLi / tetrahydrofuran; hexane / 1.) 1 h, 2.) 8 h

3: 95 percent / 1N HCl / tetrahydrofuran / 18 h / 57 °C

With hydrogenchloride; n-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo951747o

Reference yield:

: 144152-64-7
Acetic acid (1S,3S,6R,7S,8S,10S)-10-acetoxy-6-acetylamino-4-oxo-2,9-dioxa-tricyclo[4.3.1.0^3,8]dec-7-yl ester

: 174741-80-1
N-((1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-hydroxy-2-oxa-bicyclo[3.3.1]non-7-en-5-yl)-acetamide

Guidance literature:: Multi-step reaction with 4 steps

1: NaH / methanol; paraffin / 0.25 h

2: NaH, TBAI / tetrahydrofuran; dimethylformamide; paraffin / 24 h

3: 62 percent / n-BuLi / tetrahydrofuran; hexane / 1.) 1 h, 2.) 8 h

4: 95 percent / 1N HCl / tetrahydrofuran / 18 h / 57 °C

With hydrogenchloride; n-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo951747o