(3S,4S,5S,6S)-methyl 5-(benzyloxy)-2-bromo-6-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate

Base Information

Chemical Name:(3S,4S,5S,6S)-methyl 5-(benzyloxy)-2-bromo-6-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate
CAS No.:1333041-45-4
Molecular Formula:C₄₂H₅₉BrO₆Si
Molecular Weight:767.916
Hs Code.:

(3S,4S,5S,6S)-methyl 5-(benzyloxy)-2-bromo-6-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate

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Chemical Property of (3S,4S,5S,6S)-methyl 5-(benzyloxy)-2-bromo-6-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate

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Technology Process of (3S,4S,5S,6S)-methyl 5-(benzyloxy)-2-bromo-6-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate

There total 11 articles about (3S,4S,5S,6S)-methyl 5-(benzyloxy)-2-bromo-6-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate 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:

: (+)-(S)-methyl 2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)propanoate

: 1333041-45-4
(3S,4S,5S,6S)-methyl 5-(benzyloxy)-2-bromo-6-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 12 steps

1.1: diisobutylaluminium hydride / hexanes; dichloromethane / 1 h / -40 °C / Inert atmosphere

1.2: -40 °C

2.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

3.2: Saturated solution

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

4.2: 1 h / -78 °C / Inert atmosphere

5.1: titanium(IV) trichloride isopropoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

5.2: Saturated solution

6.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

6.2: -78 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C

8.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere

9.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 °C

10.1: diisobutylaluminium hydride / hexanes; dichloromethane / 1 h / -40 °C / Inert atmosphere

10.2: -40 °C

11.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

12.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -78 °C / Inert atmosphere

With dmap; oxalyl dichloride; titanium(IV) trichloride isopropoxide; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexanes; dichloromethane; cyclohexane; 4.1: Swern oxidation / 4.2: Swern oxidation / 5.1: Mukaiyama reaction / 12.1: Mukaiyama reaction;
DOI:10.1021/jo2013884

Reference yield:

: (+/-)-(3R,4S)-methyl 4-((2S,3S,6S)-6-((R)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-2-bromo-3-hydroxy-2-methylpentanoate

: 1333041-45-4
(3S,4S,5S,6S)-methyl 5-(benzyloxy)-2-bromo-6-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

1.2: -78 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C

3.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere

4.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 °C

5.1: diisobutylaluminium hydride / hexanes; dichloromethane / 1 h / -40 °C / Inert atmosphere

5.2: -40 °C

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

7.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -78 °C / Inert atmosphere

With dmap; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; hexanes; dichloromethane; cyclohexane; 7.1: Mukaiyama reaction;
DOI:10.1021/jo2013884

Reference yield:

: 1333041-87-4
(+)-(R)-2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)-propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)propan-1-ol

: 1333041-45-4
(3S,4S,5S,6S)-methyl 5-(benzyloxy)-2-bromo-6-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

2.2: Saturated solution

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: titanium(IV) trichloride isopropoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.2: Saturated solution

5.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

5.2: -78 °C / Inert atmosphere

6.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C

7.1: dmap; triethylamine / dichloromethane / 0 °C / Inert atmosphere

8.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 °C

9.1: diisobutylaluminium hydride / hexanes; dichloromethane / 1 h / -40 °C / Inert atmosphere

9.2: -40 °C

10.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

11.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -78 °C / Inert atmosphere

With dmap; oxalyl dichloride; titanium(IV) trichloride isopropoxide; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexanes; dichloromethane; cyclohexane; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Mukaiyama reaction / 11.1: Mukaiyama reaction;
DOI:10.1021/jo2013884