1-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol

Base Information

• Chemical Name: 1-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol
• CAS No.: 136538-28-8
• Molecular Formula: C₂₆H₄₈O₆Si₂
• Molecular Weight: 512.835

Synonyms:1-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol

Chemical Property of 1-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol

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Technology Process of 1-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol

There total 2 articles about 1-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol 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: 55.0%

4,4-dimethoxycyclohexa-2,5-dienone (935-50-2) + (((2S,3S,4S)-2-methyl-3,4-dihydro-2H-pyran-3,4-diyl)bis(oxy))bis(tert-butyldimethylsilane) (101856-98-8) → 1-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol (136538-28-8)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; pentane; 1.) -78 deg C, 15 min; 0 deg C, 2 h, 2.) -99 deg C to room temp., 6 h;

DOI:10.1021/jo00114a057

Reference yield:

4,4-dimethoxycyclohexa-2,5-dienone (935-50-2) + C18H37LiO3Si2 (136538-24-4) → 1-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol (136538-28-8)

Guidance literature:

DOI:10.1021/ja00022a046

Reference yield: 96.0%

1-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-4,4-dimethoxy-cyclohexa-2,5-dienol (136538-28-8) → 2-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-4-methoxy-phenol

Guidance literature:

With zinc(II) chloride; In diethyl ether; 1.) -78 deg C, 75 min, 2.) 0 deg C, 45 min;

DOI:10.1021/jo00114a057

upstream raw materials:

4,4-dimethoxycyclohexa-2,5-dienone

C₁₈H₃₇LiO₃Si₂

(((2S,3S,4S)-2-methyl-3,4-dihydro-2H-pyran-3,4-diyl)bis(oxy))bis(tert-butyldimethylsilane)

Downstream raw materials:

(2S,3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-phenyl)-2-methyl-3,4-dihydro-2H-pyran

1-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-4-methoxy-cyclohexa-2,5-dienol

(2R,3S,4R,5R,6S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-6-methyl-tetrahydro-pyran-4-ol

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