N-[(1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-(4-methoxy-benzyloxy)-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-(4-methoxy-benzyloxy)-2-oxa-bicyclo[3.3.1]non-7-en-5-yl]-acetamide
CAS No.:174741-81-2
Molecular Formula:C₃₃H₃₅NO₇
Molecular Weight:557.643
Hs Code.:

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

There total 6 articles about N-[(1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-(4-methoxy-benzyloxy)-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: 33.0%

: 105-13-5
4-Methoxybenzyl alcohol

: 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

: 174741-81-2
N-[(1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[3.3.1]non-7-en-5-yl]-acetamide

Guidance literature:: With Amberlyst 15; MS 4 Angstroem; In tetrahydrofuran; for 96h;
DOI:10.1021/jo951747o

Reference yield:

: 100-39-0
benzyl bromide

: 174741-81-2
N-[(1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[3.3.1]non-7-en-5-yl]-acetamide

Guidance literature:: Multi-step reaction with 4 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

4: 33 percent / MS 4 Angstroem, Amberlyst 15 / tetrahydrofuran / 96 h

With hydrogenchloride; n-butyllithium; Amberlyst 15; MS 4 Angstroem; 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

: 174741-81-2
N-[(1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[3.3.1]non-7-en-5-yl]-acetamide

Guidance literature:: Multi-step reaction with 5 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

5: 33 percent / MS 4 Angstroem, Amberlyst 15 / tetrahydrofuran / 96 h

With hydrogenchloride; n-butyllithium; Amberlyst 15; MS 4 Angstroem; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo951747o