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

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Chemical Name:ethyl (+)-(R)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate
CAS No.:1370254-43-5
Molecular Formula:C₂₁H₃₂O₄
Molecular Weight:348.483
Hs Code.:

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

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

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

There total 11 articles about ethyl (+)-(R)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate 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: 79.0%

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

: 1370254-43-5
ethyl (+)-(R)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate

Guidance literature:: ethyl (+)-(S)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}-2-iodopropanoate; With magnesium bromide diethyl etherate; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

With triethyl borane; tri-n-butyl-tin hydride; In dichloromethane; at -78 ℃; 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

: 1370254-43-5
ethyl (+)-(R)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0 °C / Inert atmosphere

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

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

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

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

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

7.1: magnesium bromide diethyl etherate / dichloromethane / 1 h / 0 °C / Inert atmosphere

7.2: air / -78 °C / Inert atmosphere

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

Reference yield:

: 1370254-51-5
(-)-(2S,5R,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-1-ol

: 1370254-43-5
ethyl (+)-(R)-2-{(2S,3S,6R)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

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

5.1: magnesium bromide diethyl etherate / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.2: air / -78 °C / Inert atmosphere

With iodine; silver trifluoromethanesulfonate; magnesium bromide diethyl etherate; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1055/s-0031-1289661