methyl 6-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-deoxy-4-methylene-α-D-lyxo-hexopyranoside

Base Information

Chemical Name:methyl 6-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-deoxy-4-methylene-α-D-lyxo-hexopyranoside
CAS No.:189825-47-6
Molecular Formula:C₂₇H₃₆O₅Si
Molecular Weight:468.665
Hs Code.:

Synonyms:methyl 6-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-deoxy-4-methylene-α-D-lyxo-hexopyranoside

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Chemical Property of methyl 6-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-deoxy-4-methylene-α-D-lyxo-hexopyranoside

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Technology Process of methyl 6-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-deoxy-4-methylene-α-D-lyxo-hexopyranoside

There total 2 articles about methyl 6-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-deoxy-4-methylene-α-D-lyxo-hexopyranoside 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: 81.0%

: 189825-46-5
methyl 6-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-oxo-α-D-lyxo-hexopyranoside

: 189825-47-6
methyl 6-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-deoxy-4-methylene-α-D-lyxo-hexopyranoside

Guidance literature:: In toluene; at 70 ℃; for 40h;
DOI:10.1021/ja9642929

Reference yield:

: 131089-35-5
methyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside

: 189825-47-6
methyl 6-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-deoxy-4-methylene-α-D-lyxo-hexopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / pyridinium chlorochromate, molecular sieves 4 Angstroem / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 81 percent / toluene / 40 h / 70 °C

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; toluene;
DOI:10.1021/ja9642929

Reference yield:

: 189825-47-6
methyl 6-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-deoxy-4-methylene-α-D-lyxo-hexopyranoside

: 189825-49-8
C₄₂H₆₇NO₉Si₂

Guidance literature:: Multi-step reaction with 4 steps

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

2: 1.) O₃, O₂, 2.) dimethylsulfide / 1) CH₂Cl₂, CH₃OH, -78 deg C; 2) CH₂Cl₂, CH₃OH, rt, 1.5-2 h

3: NaBH₃CN, AcOH, NaOAc / tetrahydrofuran / 2 h / Ambient temperature; pH 4

4: H₂ / Pd/C / methanol / 12 h / 2068.6 Torr

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; dimethylsulfide; hydrogen; oxygen; sodium acetate; sodium cyanoborohydride; ozone; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol;
DOI:10.1021/ja9642929