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

Base Information

• Chemical Name: methyl 6-(O-tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-O-(methoxymethyl)-α-D-mannopyranoside
• CAS No.: 189825-35-2
• Molecular Formula: C₂₈H₄₀O₇Si
• Molecular Weight: 516.707
• Mol file: 189825-35-2.mol

Synonyms:methyl 6-(O-tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-O-(methoxymethyl)-α-D-mannopyranoside

Chemical Property of methyl 6-(O-tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-O-(methoxymethyl)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-(O-tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-O-(methoxymethyl)-α-D-mannopyranoside

There total 1 articles about methyl 6-(O-tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-O-(methoxymethyl)-α-D-mannopyranoside 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: 99.0%

methyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside (131089-35-5) + chloromethyl methyl ether (107-30-2) → methyl 6-(O-tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-O-(methoxymethyl)-α-D-mannopyranoside (189825-35-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 14h; Ambient temperature;

DOI:10.1021/ja9642929

Reference yield:

methyl 6-(O-tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-O-(methoxymethyl)-α-D-mannopyranoside (189825-35-2) → C36H57NO11Si (189825-39-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 25 °C

2: 92 percent / pyridinium chlorochromate, molecular sieves 4 Angstroem / CH₂Cl₂ / 0.58 h / Ambient temperature

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

4: 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; potassium hexamethylsilazane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja9642929

upstream raw materials:

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

chloromethyl methyl ether

Downstream raw materials:

C₃₆H₅₇NO₁₁Si