Acetic acid (1S,2S)-2-[(3aS,4S,6S,7aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-1-methyl-2-p-tolylmethanesulfonylamino-ethyl ester

Base Information

• Chemical Name: Acetic acid (1S,2S)-2-[(3aS,4S,6S,7aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-1-methyl-2-p-tolylmethanesulfonylamino-ethyl ester
• CAS No.: 126423-70-9
• Molecular Formula: C₂₈H₄₇NO₇SSi
• Molecular Weight: 569.835

Synonyms:Acetic acid (1S,2S)-2-[(3aS,4S,6S,7aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-1-methyl-2-p-tolylmethanesulfonylamino-ethyl ester

Chemical Property of Acetic acid (1S,2S)-2-[(3aS,4S,6S,7aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-1-methyl-2-p-tolylmethanesulfonylamino-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of Acetic acid (1S,2S)-2-[(3aS,4S,6S,7aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-1-methyl-2-p-tolylmethanesulfonylamino-ethyl ester

There total 17 articles about Acetic acid (1S,2S)-2-[(3aS,4S,6S,7aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-1-methyl-2-p-tolylmethanesulfonylamino-ethyl ester 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: 95.0%

N-{(S)-1-[(3aS,4S,6S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-2-hydroxy-propyl}-C-p-tolyl-methanesulfonamide (126423-69-6,126574-83-2) + acetic anhydride (108-24-7) → Acetic acid (1S,2S)-2-[(3aS,4S,6S,7aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-1-methyl-2-p-tolylmethanesulfonylamino-ethyl ester (126423-70-9)

Guidance literature:

With pyridine; for 20h; Ambient temperature;

DOI:10.1021/ja00165a035

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → Acetic acid (1S,2S)-2-[(3aS,4S,6S,7aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-1-methyl-2-p-tolylmethanesulfonylamino-ethyl ester (126423-70-9)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 99 percent / toluene / -20 °C

4: pyridine / Ambient temperature

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00311a110

Reference yield:

endo-4-hydroxy-2-oxabicyclo<3.3.1>non-6-en-3-one (99440-81-0) → Acetic acid (1S,2S)-2-[(3aS,4S,6S,7aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-1-methyl-2-p-tolylmethanesulfonylamino-ethyl ester (126423-70-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 86 percent / CrO₃, pyridine / CH₂Cl₂ / Ambient temperature

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

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

4: 90 percent / mCPBA / CH₂Cl₂ / Ambient temperature

5: HCO₂H, Et₃N / methanol

6: tetrahydrofuran / Ambient temperature

7: PPTS / dimethylformamide

8: 2,6-lutidine / dimethylformamide / -10 °C

9: 89 percent / LiAlH₄ / tetrahydrofuran / -78 °C

10: 99 percent / toluene / -20 °C

11: pyridine / Ambient temperature

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

DOI:10.1021/ja00311a110

upstream raw materials:

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

acetic anhydride

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

t-butyldimethylsiyl triflate

Downstream raw materials:

Acetic acid (1S,2S)-2-((3aS,4S,6S,7aS)-6-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl)-1-methyl-2-p-tolylmethanesulfonylamino-ethyl ester

N-[(1S,2S)-1-((3aS,4S,7aS)-2,2-Dimethyl-6-oxo-hexahydro-benzo[1,3]dioxol-4-yl)-2-hydroxy-propyl]-C-p-tolyl-methanesulfonamide

N-((3aS,8S,9S,9aS,9bS)-5-Hydroxy-2,2,8-trimethyl-6-oxo-4,6,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-f]isochromen-9-yl)-C-p-tolyl-methanesulfonamide

Acetic acid (1S,2S)-2-((3aS,4S,7aS)-2,2-dimethyl-6-oxo-hexahydro-benzo[1,3]dioxol-4-yl)-1-methyl-2-p-tolylmethanesulfonylamino-ethyl ester

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