1-C-(6-acetyloxymethyl-2,4-dibenzyloxyphenyl)-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal

Base Information

• Chemical Name: 1-C-(6-acetyloxymethyl-2,4-dibenzyloxyphenyl)-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal
• CAS No.: 129896-30-6
• Molecular Formula: C₄₇H₇₂O₈Si₃
• Molecular Weight: 849.34

Synonyms:1-C-(6-acetyloxymethyl-2,4-dibenzyloxyphenyl)-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal

Chemical Property of 1-C-(6-acetyloxymethyl-2,4-dibenzyloxyphenyl)-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal

Chemical Property:

Purity/Quality:

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Technology Process of 1-C-(6-acetyloxymethyl-2,4-dibenzyloxyphenyl)-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal

There total 2 articles about 1-C-(6-acetyloxymethyl-2,4-dibenzyloxyphenyl)-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal 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: 85.0%

1-acetyloxymethyl-2-bromo-3,5-dibenzyloxybenzene (129896-29-3) + 1-tributylstannyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal (105938-00-9) → 1-C-(6-acetyloxymethyl-2,4-dibenzyloxyphenyl)-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal (129896-30-6)

Guidance literature:

bis-triphenylphosphine-palladium(II) chloride; In toluene; Heating;

DOI:10.1021/jo00310a004

Reference yield: 85.0%

1-acetyloxymethyl-2-bromo-3,5-dibenzyloxybenzene (129896-29-3) + 1-tributylstannyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal (105938-00-9) → 1-C-(6-acetyloxymethyl-2,4-dibenzyloxyphenyl)-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal (129896-30-6) + (4R,5R,6R,4'R,5'R,6'R)-4,5,4',5'-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-6,6'-bis-(tert-butyl-dimethyl-silanyloxymethyl)-5,6,5',6'-tetrahydro-4H,4'H-[2,2']bipyranyl

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In benzene; for 15h; Heating;

DOI:10.1139/v94-160

Reference yield: 96.0%

1-C-(6-acetyloxymethyl-2,4-dibenzyloxyphenyl)-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal (129896-30-6) → {3,5-Bis-benzyloxy-2-[(4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5,6-dihydro-4H-pyran-2-yl]-phenyl}-methanol (129896-31-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃;

DOI:10.1021/jo00310a004

upstream raw materials:

1-acetyloxymethyl-2-bromo-3,5-dibenzyloxybenzene

1-tributylstannyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal

Downstream raw materials:

{3,5-Bis-benzyloxy-2-[(4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5,6-dihydro-4H-pyran-2-yl]-phenyl}-methanol

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