N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-(1S,6S,7S,8S,8aS)-1,6,7,8-tetrahydroxyoctahydroindolizinium methanesulphonate

Base Information

• Chemical Name: N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-(1S,6S,7S,8S,8aS)-1,6,7,8-tetrahydroxyoctahydroindolizinium methanesulphonate
• CAS No.: 121194-95-4
• Molecular Formula: CH₃O₃S*C₃₁H₄₆NO₄Si
• Molecular Weight: 619.895
• Mol file: 121194-95-4.mol

Synonyms:

Chemical Property of N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-(1S,6S,7S,8S,8aS)-1,6,7,8-tetrahydroxyoctahydroindolizinium methanesulphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-(1S,6S,7S,8S,8aS)-1,6,7,8-tetrahydroxyoctahydroindolizinium methanesulphonate

There total 24 articles about N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-(1S,6S,7S,8S,8aS)-1,6,7,8-tetrahydroxyoctahydroindolizinium methanesulphonate 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:

benzyl bromide (100-39-0) → Methanesulfonate(3aR,8R,8aS,9R,9aR)-5-benzyl-9-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-f]indolizin-5-ium; (121194-95-4,131898-24-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) sodium hydride, 2.) tetrabutylammonium iodide / 1.) THF, 2.) 15 h

2: 1.) lithium aluminium hydride, 2.) aluminium trichloride / 1.) THF, 15 min, 2.) 15 min

3: methyl sulphoxide, oxalyl chloride, triethylamine / CH₂Cl₂ / 0.5 h

4: tetrahydrofuran / 2 h

5: 73 percent / imidazole / dimethylformamide / 15 h

6: 1.) borane-dimethyl sulphide complex, 2.) 30 percent aq. hydrogen peroxide, 3 M sodium hydroxide / 1.) THF, 30 min, 2.) 15 h

7: triethylamine / CH₂Cl₂ / 15 h

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)80146-T

Reference yield:

benzyl bromide (100-39-0) → Methanesulfonate(3aR,8S,8aS,9R,9aR)-5-benzyl-9-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-f]indolizin-5-ium; (121194-95-4,131898-24-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) sodium hydride, 2.) tetrabutylammonium iodide / 1.) THF, 2.) 15 h

2: 1.) lithium aluminium hydride, 2.) aluminium trichloride / 1.) THF, 15 min, 2.) 15 min

3: methyl sulphoxide, oxalyl chloride, triethylamine / CH₂Cl₂ / 0.5 h

4: tetrahydrofuran / 2 h

5: 73 percent / imidazole / dimethylformamide / 15 h

6: 1.) borane-dimethyl sulphide complex, 2.) 30 percent aq. hydrogen peroxide, 3 M sodium hydroxide / 1.) THF, 30 min, 2.) 15 h

7: triethylamine / CH₂Cl₂ / 15 h

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)80146-T

Reference yield:

benzyl bromide (100-39-0) → N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-(1S,6S,7S,8S,8aS)-1,6,7,8-tetrahydroxyoctahydroindolizinium methanesulphonate (121194-95-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) sodium hydride, 2.) tetrabutylammonium iodide / 1.) THF, 2.) 15 h

2: 1.) lithium aluminium hydride, 2.) aluminium trichloride / 1.) THF, 15 min, 2.) 15 min

3: methyl sulphoxide, oxalyl chloride, triethylamine / CH₂Cl₂ / 0.5 h

4: tetrahydrofuran / 2 h

5: 85 percent / imidazole / dimethylformamide / 15 h

6: 1.) diborane, 2.) 30 percent aq. hydrogen peroxide, 3 M sodium hydroxide / 1.) THF, 30 min, 2.) 15 h

7: triethylamine / CH₂Cl₂ / 15 h

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; diborane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)80146-T

upstream raw materials:

N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-1,5,7-trideoxy-1,5-imino-2,3-O-isopropylidene-L-glycero-D-manno-octitol

methanesulfonyl chloride

benzyl bromide

6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-D-mannono-δ-lactam

Downstream raw materials:

L-6-epicastanospermine

6-epi-castanospermine