((2R,3S,4S,6S)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Base Information

Chemical Name:((2R,3S,4S,6S)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane
CAS No.:143293-29-2
Molecular Formula:C₂₉H₄₂O₄Si
Molecular Weight:482.736
Hs Code.:

Synonyms:((2R,3S,4S,6S)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

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Chemical Property of ((2R,3S,4S,6S)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

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Technology Process of ((2R,3S,4S,6S)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

There total 7 articles about ((2R,3S,4S,6S)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane 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: 96.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 147806-44-8
(2R,3S,4S,6S)-2-allyl-4-benzyloxy-6-benzyloxymethyl-tetrahydropyran-3-ol

: 143293-29-2
((2R,3S,4S,6S)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/ja00046a063

Reference yield:

: 132375-56-5
((3aR,4R,6S,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol

: 143293-29-2
((2R,3S,4S,6S)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / 25 °C

2: 98 percent / TFA / toluene / 0.25 h / 0 °C

3: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, 60 deg C, 1.5 h, 2.) DMF, 25 deg C, 16 h

4: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; cesium fluoride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;

Reference yield:

: 122821-81-2
2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol

: 143293-29-2
((2R,3S,4S,6S)-2-Allyl-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

2: 90 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / 25 °C

3: 98 percent / TFA / toluene / 0.25 h / 0 °C

4: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, 60 deg C, 1.5 h, 2.) DMF, 25 deg C, 16 h

5: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; cesium fluoride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;