N-[(1R,3S,4S,5R,8S,9S)-4,9-Bis-benzyloxy-8-hydroxy-3-(4-methoxy-benzyloxy)-7-methylene-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

Base Information

Chemical Name:N-[(1R,3S,4S,5R,8S,9S)-4,9-Bis-benzyloxy-8-hydroxy-3-(4-methoxy-benzyloxy)-7-methylene-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide
CAS No.:174741-85-6
Molecular Formula:C₃₃H₃₇NO₇
Molecular Weight:559.659
Hs Code.:

Synonyms:N-[(1R,3S,4S,5R,8S,9S)-4,9-Bis-benzyloxy-8-hydroxy-3-(4-methoxy-benzyloxy)-7-methylene-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

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Chemical Property of N-[(1R,3S,4S,5R,8S,9S)-4,9-Bis-benzyloxy-8-hydroxy-3-(4-methoxy-benzyloxy)-7-methylene-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

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Technology Process of N-[(1R,3S,4S,5R,8S,9S)-4,9-Bis-benzyloxy-8-hydroxy-3-(4-methoxy-benzyloxy)-7-methylene-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

There total 10 articles about N-[(1R,3S,4S,5R,8S,9S)-4,9-Bis-benzyloxy-8-hydroxy-3-(4-methoxy-benzyloxy)-7-methylene-2-oxa-bicyclo[3.3.1]non-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: 96.0%

: 174741-84-5
N-[(1S,2S,4S,6R,7S,8S,10S)-7,10-Bis-benzyloxy-4-iodomethyl-8-(4-methoxy-benzyloxy)-3,9-dioxa-tricyclo[4.3.1.0^2,4]dec-6-yl]-acetamide

: 174741-85-6
N-[(1R,3S,4S,5R,8S,9S)-4,9-Bis-benzyloxy-8-hydroxy-3-(4-methoxy-benzyloxy)-7-methylene-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

Guidance literature:: With zinc; In ethanol; for 2h; Heating;
DOI:10.1021/jo951747o

Reference yield:

: 100-39-0
benzyl bromide

: 174741-85-6
N-[(1R,3S,4S,5R,8S,9S)-4,9-Bis-benzyloxy-8-hydroxy-3-(4-methoxy-benzyloxy)-7-methylene-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

Guidance literature:: Multi-step reaction with 8 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

5: 87 percent / CeCl₃*7H₂O, NaBH₄ / ethanol; H₂O / 0.17 h / -10 °C

6: 74 percent / NaHCO₃, MCPBA / CH₂Cl₂ / 36 h

7: 92 percent / PPh₃, imidazole, I₂ / toluene / 10 h / 47 °C

8: 96 percent / Zn / ethanol / 2 h / Heating

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; Amberlyst 15; cerium(III) chloride; MS 4 Angstroem; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 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

: 174741-85-6
N-[(1R,3S,4S,5R,8S,9S)-4,9-Bis-benzyloxy-8-hydroxy-3-(4-methoxy-benzyloxy)-7-methylene-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

Guidance literature:: Multi-step reaction with 9 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

6: 87 percent / CeCl₃*7H₂O, NaBH₄ / ethanol; H₂O / 0.17 h / -10 °C

7: 74 percent / NaHCO₃, MCPBA / CH₂Cl₂ / 36 h

8: 92 percent / PPh₃, imidazole, I₂ / toluene / 10 h / 47 °C

9: 96 percent / Zn / ethanol / 2 h / Heating

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; Amberlyst 15; cerium(III) chloride; MS 4 Angstroem; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; paraffin;
DOI:10.1021/jo951747o