N-[(1R,5R,6R,7R,10R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dioxa-tricyclo[3.3.1.1^3,7]dec-10-yl]-C-p-tolyl-methanesulfonamide

Base Information

• Chemical Name: N-[(1R,5R,6R,7R,10R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dioxa-tricyclo[3.3.1.1^3,7]dec-10-yl]-C-p-tolyl-methanesulfonamide
• CAS No.: 126423-67-4
• Molecular Formula: C₂₈H₄₉NO₆SSi₂
• Molecular Weight: 583.937

Synonyms:N-[(1R,5R,6R,7R,10R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dioxa-tricyclo[3.3.1.1^3,7]dec-10-yl]-C-p-tolyl-methanesulfonamide

Chemical Property of N-[(1R,5R,6R,7R,10R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dioxa-tricyclo[3.3.1.1^3,7]dec-10-yl]-C-p-tolyl-methanesulfonamide

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Technology Process of N-[(1R,5R,6R,7R,10R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dioxa-tricyclo[3.3.1.1^3,7]dec-10-yl]-C-p-tolyl-methanesulfonamide

There total 15 articles about N-[(1R,5R,6R,7R,10R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dioxa-tricyclo[3.3.1.1^3,7]dec-10-yl]-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: 60.0%

t-butyldimethylsiyl triflate (69739-34-0) + N-((1S,4S,5S,6S,7S)-6,7-Dihydroxy-3-oxo-2-oxa-bicyclo[3.3.1]non-4-yl)-C-p-tolyl-methanesulfonamide (126423-63-0) → N-[(1R,5R,6R,7R,10R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dioxa-tricyclo[3.3.1.13,7]dec-10-yl]-C-p-tolyl-methanesulfonamide (126423-67-4)

Guidance literature:

With 2,6-dimethylpyridine; In N,N-dimethyl-formamide; at -10 ℃;

DOI:10.1021/ja00311a110

Reference yield: 50.0%

t-butyldimethylsiyl triflate (69739-34-0) + N-((1S,4S,5S,6S,7S)-6,7-Dihydroxy-3-oxo-2-oxa-bicyclo[3.3.1]non-4-yl)-C-p-tolyl-methanesulfonamide (126423-63-0) → N-[(1R,3S,5R,6R,7S,10R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dioxa-tricyclo[3.3.1.13,7]dec-10-yl]-C-p-tolyl-methanesulfonamide (126423-67-4)

Guidance literature:

With 2,6-dimethylpyridine; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

DOI:10.1021/ja00165a035

Reference yield:

endo-4-hydroxy-2-oxabicyclo<3.3.1>non-6-en-3-one (99440-81-0) → N-[(1R,5R,6R,7R,10R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dioxa-tricyclo[3.3.1.13,7]dec-10-yl]-C-p-tolyl-methanesulfonamide (126423-67-4)

Guidance literature:

Multi-step reaction with 6 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: 60 percent / 2,6-lutidine / dimethylformamide / -10 °C

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

DOI:10.1021/ja00311a110

upstream raw materials:

t-butyldimethylsiyl triflate

N-((1S,4S,5S,6S,7S)-6,7-Dihydroxy-3-oxo-2-oxa-bicyclo[3.3.1]non-4-yl)-C-p-tolyl-methanesulfonamide

Oxo-acetic acid cyclohex-3-enyl ester

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

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