(2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

Base Information

Chemical Name:(2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran
CAS No.:657389-53-2
Molecular Formula:C₂₅H₄₂O₅Si
Molecular Weight:450.691
Hs Code.:

Synonyms:(2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

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Chemical Property of (2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

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Technology Process of (2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

There total 5 articles about (2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran 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:

: 3-[(2R,3S,4S,5R,6R)-6-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propane-1,2-diol

: 657389-53-2
(2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

Guidance literature:: With sodium periodate; silica gel; In dichloromethane; for 1.5h;
DOI:10.1039/b308305e

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 657389-53-2
(2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 - 20 °C

2: OsO₄; aq. NMO / 2-methyl-propan-2-ol; acetone / 24 h / 20 °C

3: 90 mg / NaIO₄; silica / CH₂Cl₂ / 1.5 h

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; silica gel; In dichloromethane; acetone; tert-butyl alcohol;
DOI:10.1039/b308305e

Reference yield:

: (2R,3R,4R,5R)-2-allyl-6-(oxiranyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

: 657389-53-2
(2R,3R,4R,5R,6S)-2-(2-oxoethyl)-6-((S)-1-tert-butyldimethylsilanyloxyethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / LiAlH₄ / diethyl ether / 2 h

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 - 20 °C

3: OsO₄; aq. NMO / 2-methyl-propan-2-ol; acetone / 24 h / 20 °C

4: 90 mg / NaIO₄; silica / CH₂Cl₂ / 1.5 h

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; silica gel; In diethyl ether; dichloromethane; acetone; tert-butyl alcohol;
DOI:10.1039/b308305e