N-[(1S,3S,4S,5R,8R,9S)-4,9-Bis-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-7-oxo-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

Base Information

Chemical Name:N-[(1S,3S,4S,5R,8R,9S)-4,9-Bis-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-7-oxo-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide
CAS No.:174741-87-8
Molecular Formula:C₃₈H₄₉NO₈Si
Molecular Weight:675.894
Hs Code.:

N-[(1S,3S,4S,5R,8R,9S)-4,9-Bis-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-7-oxo-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

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

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

There total 13 articles about N-[(1S,3S,4S,5R,8R,9S)-4,9-Bis-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-7-oxo-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:

: 69739-34-0
t-butyldimethylsiyl triflate

: 174741-87-8
N-[(1S,3S,4S,5R,8R,9S)-4,9-Bis-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-7-oxo-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / Et₃N / CH₂Cl₂ / 8 h

2: 1.) O₃, pyridine, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) room temperature, 30 min

With pyridine; dimethylsulfide; ozone; triethylamine; In dichloromethane;
DOI:10.1021/jo951747o

Reference yield:

: 100-39-0
benzyl bromide

: 174741-87-8
N-[(1S,3S,4S,5R,8R,9S)-4,9-Bis-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-7-oxo-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

Guidance literature:: Multi-step reaction with 10 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

9: 86 percent / Et₃N / CH₂Cl₂ / 8 h

10: 1.) O₃, pyridine, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) room temperature, 30 min

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; Amberlyst 15; cerium(III) chloride; dimethylsulfide; MS 4 Angstroem; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; ozone; triethylamine; 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

: 174741-87-8
N-[(1S,3S,4S,5R,8R,9S)-4,9-Bis-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-7-oxo-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

Guidance literature:: Multi-step reaction with 11 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

10: 86 percent / Et₃N / CH₂Cl₂ / 8 h

11: 1.) O₃, pyridine, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) room temperature, 30 min

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