(1R,2R,4R,5R,6R)-2-exo-[((S)-N-methyl-S-phenylsulfonimidoyl)methyl]-5,6-bis[[(tert-butyl)dimethylsilyl]oxy]-7-oxabicyclo[2.2.1]heptan-2-ol

Base Information

• Chemical Name: (1R,2R,4R,5R,6R)-2-exo-[((S)-N-methyl-S-phenylsulfonimidoyl)methyl]-5,6-bis[[(tert-butyl)dimethylsilyl]oxy]-7-oxabicyclo[2.2.1]heptan-2-ol
• CAS No.: 218621-56-8
• Molecular Formula: C₂₆H₄₇NO₅SSi₂
• Molecular Weight: 541.9
• Mol file: 218621-56-8.mol

Synonyms:

Chemical Property of (1R,2R,4R,5R,6R)-2-exo-[((S)-N-methyl-S-phenylsulfonimidoyl)methyl]-5,6-bis[[(tert-butyl)dimethylsilyl]oxy]-7-oxabicyclo[2.2.1]heptan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,4R,5R,6R)-2-exo-[((S)-N-methyl-S-phenylsulfonimidoyl)methyl]-5,6-bis[[(tert-butyl)dimethylsilyl]oxy]-7-oxabicyclo[2.2.1]heptan-2-ol

There total 1 articles about (1R,2R,4R,5R,6R)-2-exo-[((S)-N-methyl-S-phenylsulfonimidoyl)methyl]-5,6-bis[[(tert-butyl)dimethylsilyl]oxy]-7-oxabicyclo[2.2.1]heptan-2-ol 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: 42.0%

(1RS,4RS,5RS,6RS)-5-exo,6-endo-bis{[(tert-butyl)dimrthylsilyl]oxy}-7-oxabicyclo[2.2.1]heptan-2-one (123155-32-8,129829-55-6,129829-64-7) + N,S-dimethyl-S-phenylsulfoximine (33993-53-2) → (1R,2R,4R,5R,6R)-2-exo-[((S)-N-methyl-S-phenylsulfonimidoyl)methyl]-5,6-bis[[(tert-butyl)dimethylsilyl]oxy]-7-oxabicyclo[2.2.1]heptan-2-ol (218621-56-8) + (1S,2S,4S,5S,6S)-2-exo-[((S)-N-methyl-S-phenylsulfonimidoyl)methyl]-5,6-bis[[(tert-butyl)dimethylsilyl]oxy]-7-oxabicyclo[2.2.1]heptan-2-ol (218621-57-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1.) -25 deg C; 0 deg C, 10 min; 2.) -78 deg C, 1 h;

DOI:10.1002/(SICI)1522-2675(19981111)81:11<2043::AID-HLCA2043>3.0.CO;2-6

Reference yield:

(1R,2R,4R,5R,6R)-2-exo-[((S)-N-methyl-S-phenylsulfonimidoyl)methyl]-5,6-bis[[(tert-butyl)dimethylsilyl]oxy]-7-oxabicyclo[2.2.1]heptan-2-ol (218621-56-8) → 4-Ethyl-7-[(1R,2S,3S,4R)-2,3,4-tris-(tert-butyl-dimethyl-silanyloxy)-cyclohexyloxy]-chromen-2-one (218621-54-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / 0.2 Torr / 50 deg C, 5 min; 100 deg C, 5 min; 150 deg C, 4 min; 180 deg C, 2 min; 190 deg C, 5 min; 200 deg C, 6 min

2: Et₃N

3: NaBH₄, CeCl₃*7H₂O

4: 63 percent / 1,1'-(azodicarbonyl)bispiperidine, (Bu)3P / tetrahydrofuran / 25 deg C, 15 min; 0 deg C, 3 h; 20 deg C, 18 h

5: 92 percent / H₂ / 20percent Pd(OH)2/C / ethyl acetate / 0.67 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride; tributylphosphine; hydrogen; triethylamine; 1,1'-azodicarbonyl-dipiperidine; palladium dihydroxide; In tetrahydrofuran; ethyl acetate;

DOI:10.1002/(SICI)1522-2675(19981111)81:11<2043::AID-HLCA2043>3.0.CO;2-6

Reference yield:

(1R,2R,4R,5R,6R)-2-exo-[((S)-N-methyl-S-phenylsulfonimidoyl)methyl]-5,6-bis[[(tert-butyl)dimethylsilyl]oxy]-7-oxabicyclo[2.2.1]heptan-2-ol (218621-56-8) → 4-Ethyl-7-((1R,2R,3S,4R)-2,3,4-trihydroxy-cyclohexyloxy)-chromen-2-one (213037-83-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / 0.2 Torr / 50 deg C, 5 min; 100 deg C, 5 min; 150 deg C, 4 min; 180 deg C, 2 min; 190 deg C, 5 min; 200 deg C, 6 min

2: Et₃N

3: NaBH₄, CeCl₃*7H₂O

4: 63 percent / 1,1'-(azodicarbonyl)bispiperidine, (Bu)3P / tetrahydrofuran / 25 deg C, 15 min; 0 deg C, 3 h; 20 deg C, 18 h

5: 92 percent / H₂ / 20percent Pd(OH)2/C / ethyl acetate / 0.67 h / 20 °C

6: 93 percent / 40percent aq.HF / acetonitrile; toluene / 24 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride; tributylphosphine; hydrogen fluoride; hydrogen; triethylamine; 1,1'-azodicarbonyl-dipiperidine; palladium dihydroxide; In tetrahydrofuran; ethyl acetate; toluene; acetonitrile;

DOI:10.1002/(SICI)1522-2675(19981111)81:11<2043::AID-HLCA2043>3.0.CO;2-6

upstream raw materials:

(1RS,4RS,5RS,6RS)-5-exo,6-endo-bis{[(tert-butyl)dimrthylsilyl]oxy}-7-oxabicyclo[2.2.1]heptan-2-one

N,S-dimethyl-S-phenylsulfoximine

Downstream raw materials:

4-Ethyl-7-((1R,2R,3S,4R)-2,3,4-trihydroxy-cyclohexyloxy)-chromen-2-one

4-Ethyl-7-[(1R,2S,3S,4R)-2,3,4-tris-(tert-butyl-dimethyl-silanyloxy)-cyclohexyloxy]-chromen-2-one