ethyl (+)-(S)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}-2-iodopropanoate

Base Information

Chemical Name:ethyl (+)-(S)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}-2-iodopropanoate
CAS No.:1370254-39-9
Molecular Formula:C₂₁H₃₁IO₄
Molecular Weight:474.379
Hs Code.:

Synonyms:ethyl (+)-(S)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}-2-iodopropanoate

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Chemical Property of ethyl (+)-(S)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}-2-iodopropanoate

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Technology Process of ethyl (+)-(S)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}-2-iodopropanoate

There total 10 articles about ethyl (+)-(S)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}-2-iodopropanoate 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:

: 1370254-35-5
ethyl (+)-(4S,7R,8R,E)-9-(benzyloxy)-7-hydroxy-2,4,8-trimethylnon-2-enoate

: 1370254-39-9
ethyl (+)-(S)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}-2-iodopropanoate

Guidance literature:: With iodine; silver trifluoromethanesulfonate; sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1055/s-0031-1289661

Reference yield:

: 1370254-47-9
(+)-(2R,3R,6S)-1-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-3-ol

: 1370254-39-9
ethyl (+)-(S)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}-2-iodopropanoate

Guidance literature:: Multi-step reaction with 6 steps

1: 2,6-dimethylpyridine / dichloromethane / 0 °C / Inert atmosphere

2: pyridine hydrogenfluoride / tetrahydrofuran / 0 °C / Inert atmosphere

3: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

4: toluene / 18 h / 20 °C / Reflux; Inert atmosphere

5: pyridine hydrogenfluoride / tetrahydrofuran / 0 °C / Inert atmosphere

6: iodine; silver trifluoromethanesulfonate; sodium hydrogencarbonate / tetrahydrofuran / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; iodine; silver trifluoromethanesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1055/s-0031-1289661

Reference yield:

: 1370254-31-1
(+)-(2S,5R,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptanal

: 1370254-39-9
ethyl (+)-(S)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}-2-iodopropanoate

Guidance literature:: Multi-step reaction with 3 steps

1: toluene / 18 h / 20 °C / Reflux; Inert atmosphere

2: pyridine hydrogenfluoride / tetrahydrofuran / 0 °C / Inert atmosphere

3: iodine; silver trifluoromethanesulfonate; sodium hydrogencarbonate / tetrahydrofuran / 20 °C / Inert atmosphere

With iodine; silver trifluoromethanesulfonate; sodium hydrogencarbonate; pyridine hydrogenfluoride; In tetrahydrofuran; toluene;
DOI:10.1055/s-0031-1289661