methyl 6-O-(tert-butyldiphenylsilyl)-2,3,4-tri-O-(methoxymethyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 6-O-(tert-butyldiphenylsilyl)-2,3,4-tri-O-(methoxymethyl)-α-D-glucopyranoside
CAS No.:189825-41-0
Molecular Formula:C₂₉H₄₄O₉Si
Molecular Weight:564.748
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 1 articles about methyl 6-O-(tert-butyldiphenylsilyl)-2,3,4-tri-O-(methoxymethyl)-α-D-glucopyranoside 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:

: 58479-62-2
(2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol

: 107-30-2
chloromethyl methyl ether

: 189825-41-0
methyl 6-O-(tert-butyldiphenylsilyl)-2,3,4-tri-O-(methoxymethyl)-α-D-glucopyranoside

Guidance literature:: With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 20h; Ambient temperature;
DOI:10.1021/ja9642929

Reference yield:

: 189825-41-0
methyl 6-O-(tert-butyldiphenylsilyl)-2,3,4-tri-O-(methoxymethyl)-α-D-glucopyranoside

: 189825-44-3
{(3aR,4R,5R,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7-[2-((2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris-methoxymethoxy-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 25 °C

2: 1.) DMSO, trifluoroacetic anhydride, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min; 2) CH₂Cl₂, -78 deg C --> rt, 10 min, rt, 20 min

3: 1.) potassium bis(trimethylsilyl)amide / 1) THF, toluene, rt, 1 h; 2) THF, toluene, -78 deg C, 30 min, rt, 18 h

4: 1.) 9-BBN-H, 2.) aq. K₃PO₄, PdCl₂(dppf) / 1) THF, reflux, 6 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; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran;
DOI:10.1021/ja9642929