N-{(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-oxo-acetamide

Base Information

Chemical Name:N-{(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-oxo-acetamide
CAS No.:210691-95-5
Molecular Formula:C₃₆H₅₇NO₉SeSi
Molecular Weight:754.895
Hs Code.:

N-{(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-oxo-acetamide

Synonyms:N-{(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-oxo-acetamide

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Chemical Property of N-{(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-oxo-acetamide

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Technology Process of N-{(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-oxo-acetamide

There total 19 articles about N-{(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-oxo-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: 55.0%

: C₁₄H₁₇LiOSe

: 210691-94-4
(1R,5S,6S,8R,10S)-8-{(2S)-3-[(tert-Butyldimethylsilyl)oxy]-2-methoxypropyl}-10-methoxy-9,9-dimethyl-5-[N-(methoxalyl)amino]-2,4,7-trioxabicyclo[4.4.0]decane

: 210691-95-5
N-{(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-oxo-acetamide

Guidance literature:: With N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at -80 ℃; for 0.5h;
DOI:10.1055/s-1998-1803

Reference yield:

: {(4R,4aR,6R,8S,8aR)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-methanol

: 210691-95-5
N-{(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-oxo-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: RuCl₃, NaIO₄ / acetonitrile; CCl₄; H₂O / 3.5 h / Ambient temperature

2: 57 percent / (PhO)2PON₃, EtN(i-Pr)2, molecular sieves 4 Angstroem / toluene / 65 °C

3: 70 percent / KHMDS / tetrahydrofuran / 1.) -95 deg C, 30 min, 2.) -90 deg C to -20 deg C, 100 min

4: 82 percent / TBAF*3H₂O, AcOH / tetrahydrofuran / 0.5 h / Ambient temperature

5: 55 percent / TMEDA / tetrahydrofuran / 0.5 h / -80 °C

With ruthenium trichloride; sodium periodate; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; tetrachloromethane; water; toluene; acetonitrile;
DOI:10.1055/s-1998-1803

Reference yield:

: 210691-88-6
(1R,5R,6R,8R,10S)-5-(tert-Butylcarbonyloxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

: 210691-95-5
N-{(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-oxo-acetamide

Guidance literature:: Multi-step reaction with 9 steps

1: Sharpless asymmetric dihydroxylation

2: DMAP, Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

3: 73 percent / 2,6-di-t-Bu-4-methylpyridine / toluene / 6 h / 70 °C

4: DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

5: RuCl₃, NaIO₄ / acetonitrile; CCl₄; H₂O / 3.5 h / Ambient temperature

6: 57 percent / (PhO)2PON₃, EtN(i-Pr)2, molecular sieves 4 Angstroem / toluene / 65 °C

7: 70 percent / KHMDS / tetrahydrofuran / 1.) -95 deg C, 30 min, 2.) -90 deg C to -20 deg C, 100 min

8: 82 percent / TBAF*3H₂O, AcOH / tetrahydrofuran / 0.5 h / Ambient temperature

9: 55 percent / TMEDA / tetrahydrofuran / 0.5 h / -80 °C

With dmap; ruthenium trichloride; sodium periodate; 2,6-di-tert-butyl-4-methylpyridine; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; diisobutylaluminium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1055/s-1998-1803