(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

Base Information

• Chemical Name: (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
• CAS No.: 126423-66-3
• Molecular Formula: C₂₇H₄₆N₂O₇SSi
• Molecular Weight: 570.823

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 12 articles about (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 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: 97.0%

t-butyldimethylsiyl triflate (69739-34-0) + (S)-2-((3aS,4S,6S,7aS)-6-Hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl)-N-methoxy-N-methyl-2-p-tolylmethanesulfonylamino-acetamide (126423-65-2) → (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 (126423-66-3)

Guidance literature:

With 2,6-dimethylpyridine; In N,N-dimethyl-formamide; at -15 ℃; for 2h;

DOI:10.1021/ja00165a035

Reference yield:

endo-4-hydroxy-2-oxabicyclo<3.3.1>non-6-en-3-one (99440-81-0) → (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 (126423-66-3)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; 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;

DOI:10.1021/ja00311a110

Reference yield:

Oxo-acetic acid cyclohex-3-enyl ester (99440-80-9) → (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 (126423-66-3)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; 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

upstream raw materials:

t-butyldimethylsiyl triflate

(S)-2-((3aS,4S,6S,7aS)-6-Hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl)-N-methoxy-N-methyl-2-p-tolylmethanesulfonylamino-acetamide

Oxo-acetic acid cyclohex-3-enyl ester

endo-4-hydroxy-2-oxabicyclo<3.3.1>non-6-en-3-one

Downstream 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-oxo-ethyl}-C-p-tolyl-methanesulfonamide

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

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-((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

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