N-{(S)-1-[(3aS,4S,6S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-2-oxo-ethyl}-C-p-tolyl-methanesulfonamide

Base Information

Chemical Name:N-{(S)-1-[(3aS,4S,6S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-2-oxo-ethyl}-C-p-tolyl-methanesulfonamide
CAS No.:126423-68-5
Molecular Formula:C₂₅H₄₁NO₆SSi
Molecular Weight:511.755
Hs Code.:

Synonyms:N-{(S)-1-[(3aS,4S,6S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-2-oxo-ethyl}-C-p-tolyl-methanesulfonamide

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Chemical Property of N-{(S)-1-[(3aS,4S,6S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-2-oxo-ethyl}-C-p-tolyl-methanesulfonamide

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Technology Process of N-{(S)-1-[(3aS,4S,6S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-2-oxo-ethyl}-C-p-tolyl-methanesulfonamide

There total 14 articles about N-{(S)-1-[(3aS,4S,6S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-2-oxo-ethyl}-C-p-tolyl-methanesulfonamide 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: 92.0%

: 126423-66-3
(R)-2-[(3aR,4R,6R,7aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-N-methoxy-N-methyl-2-p-tolylmethanesulfonylamino-acetamide

: 126423-68-5
N-{(S)-1-[(3aS,4S,6S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-2-oxo-ethyl}-C-p-tolyl-methanesulfonamide

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 ℃; for 1.5h;
DOI:10.1021/ja00165a035

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 126423-68-5
N-{(S)-1-[(3aS,4S,6S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-2-oxo-ethyl}-C-p-tolyl-methanesulfonamide

Guidance literature:: Multi-step reaction with 2 steps

1: 2,6-lutidine / dimethylformamide / -10 °C

2: 89 percent / LiAlH₄ / tetrahydrofuran / -78 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ja00311a110

Reference yield:

: 99440-80-9
Oxo-acetic acid cyclohex-3-enyl ester

: 126423-68-5
N-{(S)-1-[(3aS,4S,6S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-2-oxo-ethyl}-C-p-tolyl-methanesulfonamide

Guidance literature:: Multi-step reaction with 10 steps

1: 60 percent / SnCl₄ / nitromethane / Ambient temperature

2: 86 percent / CrO₃, pyridine / CH₂Cl₂ / Ambient temperature

3: BF₃*Et₂O / 1,2-dichloro-ethane / 42 °C

4: NaCNBH₃ / 2-methyl-butan-2-ol / Ambient temperature

5: 90 percent / mCPBA / CH₂Cl₂ / Ambient temperature

6: HCO₂H, Et₃N / methanol

7: tetrahydrofuran / Ambient temperature

8: PPTS / dimethylformamide

9: 2,6-lutidine / dimethylformamide / -10 °C

10: 89 percent / LiAlH₄ / tetrahydrofuran / -78 °C

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; lithium aluminium tetrahydride; formic acid; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; tin(IV) chloride; sodium cyanoborohydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; tert-Amyl alcohol; nitromethane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00311a110