C₃₆H₅₇NO₁₁Si

Base Information

• Chemical Name: C₃₆H₅₇NO₁₁Si
• CAS No.: 189825-39-6
• Molecular Formula: C₃₆H₅₇NO₁₁Si
• Molecular Weight: 707.934
• Mol file: 189825-39-6.mol

Synonyms:C₃₆H₅₇NO₁₁Si

Chemical Property of C₃₆H₅₇NO₁₁Si

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₃₆H₅₇NO₁₁Si

There total 10 articles about C₃₆H₅₇NO₁₁Si 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:

(1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol (130669-74-8) → C36H57NO11Si (189825-39-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / LiCl / tetrahydrofuran; nitromethane / 96 h / Ambient temperature

2: 76 percent / NaN₃ / dimethylformamide / 40 h / 55 °C

3: 99 percent / imidazole / dimethylformamide / 18 h / 60 °C

4: 1.) Ph₃P, 2.) H₂O / 1) THF, rt, 2 h; 2) THF, reflux, 6 h

5: aq. NaHCO₃ / ethyl acetate / 16 h / Ambient temperature

6: 1.) 9-BBN-H, 2.) aq. K₃PO₄, PdCl₂(dppf) / 1) THF, rt, 3 h; 2) THF, DMF, rt, 18 h

With 1H-imidazole; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; sodium azide; water; sodium hydrogencarbonate; triphenylphosphine; lithium chloride; In tetrahydrofuran; nitromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja9642929

Reference yield:

methyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside (131089-35-5) → C36H57NO11Si (189825-39-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / (i-Pr)2NEt, Bu₄N⁽¹⁺⁾*I^(1-) / CH₂Cl₂ / 14 h / Ambient temperature

2: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 25 °C

3: 92 percent / pyridinium chlorochromate, molecular sieves 4 Angstroem / CH₂Cl₂ / 0.58 h / Ambient temperature

4: 1.) potassium bis(trimethylsilyl)amide / 1) THF, toluene, rt, 1.5 h; 2) THF, toluene, -78 deg C, 15 min, rt, 1.5 h

5: 1.) 9-BBN-H, 2.) aq. K₃PO₄, PdCl₂(dppf) / 1) THF, rt, 3 h; 2) THF, DMF, rt, 18 h

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja9642929

Reference yield:

(1S,2S,5S,6S)-4-bromo-2-chloro-5,6-(O-isopropylidenedioxy)cyclohex-3-en-1-ol (189825-32-9) → C36H57NO11Si (189825-39-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / NaN₃ / dimethylformamide / 40 h / 55 °C

2: 99 percent / imidazole / dimethylformamide / 18 h / 60 °C

3: 1.) Ph₃P, 2.) H₂O / 1) THF, rt, 2 h; 2) THF, reflux, 6 h

4: aq. NaHCO₃ / ethyl acetate / 16 h / Ambient temperature

5: 1.) 9-BBN-H, 2.) aq. K₃PO₄, PdCl₂(dppf) / 1) THF, rt, 3 h; 2) THF, DMF, rt, 18 h

With 1H-imidazole; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; sodium azide; water; sodium hydrogencarbonate; triphenylphosphine; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja9642929

upstream raw materials:

[(3aR,4R,5R,7aS)-7-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-carbamic acid benzyl ester

methyl 2,3-O-isopropylidene-4-O-(methoxymethyl)-6-methylene-α-D-mannopyranoside

(1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol

methyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside