(5S,6S)-5-(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydro-2H-pyran-2-one

Base Information

Chemical Name:(5S,6S)-5-(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydro-2H-pyran-2-one
CAS No.:174270-87-2
Molecular Formula:C₁₉H₂₈O₄Si
Molecular Weight:348.514
Hs Code.:

Synonyms:(5S,6S)-5-(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydro-2H-pyran-2-one

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Chemical Property of (5S,6S)-5-(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydro-2H-pyran-2-one

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Technology Process of (5S,6S)-5-(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydro-2H-pyran-2-one

There total 10 articles about (5S,6S)-5-(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydro-2H-pyran-2-one 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: 93.0%

: 100906-41-0
(5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 174270-87-2
(5S,6S)-5-(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 5h;
DOI:10.1016/0957-4166(96)00424-7

Reference yield:

: 38270-72-3
dimethyl 2,3-O-benzylidene-L-tartrate

: 174270-87-2
(5S,6S)-5-(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 93 percent / AlCl₃, LiAlH₄ / diethyl ether; CH₂Cl₂ / 1.) RT, 1 h, 2.) reflux, 3 h

2: 94 percent / TsOH / 12 h / Ambient temperature

3: dimethyl sulfide, N-chlorosuccinimide / 1.) toluene, 6 h, 2.) toluene, from -25 deg C to RT

4: methanol / 20 h

5: 92 percent / 0.5 N aq. LiOH / tetrahydrofuran; methanol / 1 h / Ambient temperature

6: 86 percent / aq. CF₃CO₂H / 7 h / 0 - 20 °C

7: 93 percent / DMAP, Et₃N / CH₂Cl₂ / 5 h

With dmap; lithium hydroxide; N-chloro-succinimide; lithium aluminium tetrahydride; aluminium trichloride; dimethylsulfide; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1016/0957-4166(96)00424-7

Reference yield:

: 84379-51-1,84379-52-2,124909-02-0,127000-44-6
2-O-benzyl-L-threitol

: 174270-87-2
(5S,6S)-5-(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / TsOH / 12 h / Ambient temperature

2: dimethyl sulfide, N-chlorosuccinimide / 1.) toluene, 6 h, 2.) toluene, from -25 deg C to RT

3: methanol / 20 h

4: 92 percent / 0.5 N aq. LiOH / tetrahydrofuran; methanol / 1 h / Ambient temperature

5: 86 percent / aq. CF₃CO₂H / 7 h / 0 - 20 °C

6: 93 percent / DMAP, Et₃N / CH₂Cl₂ / 5 h

With dmap; lithium hydroxide; N-chloro-succinimide; dimethylsulfide; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/0957-4166(96)00424-7