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

Base Information

Chemical Name:(2R,3S,4S,5S,6S)-methyl 5-(benzyloxy)-6-((2S,3S,6S)-6-((R)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate
CAS No.:1333041-33-0
Molecular Formula:C₃₃H₄₈O₆
Molecular Weight:540.741
Hs Code.:

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

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

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

There total 11 articles about (2R,3S,4S,5S,6S)-methyl 5-(benzyloxy)-6-((2S,3S,6S)-6-((R)-1-(benzyloxy)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: 66.0%

: 1333041-25-0
(3S,4S,5S,6S)-methyl 5-(benzyloxy)-6-((2S,3S,6S)-6-((R)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-2-bromo-3-hydroxy-2,4-dimethylheptanoate

: 1333041-33-0
(2R,3S,4S,5S,6S)-methyl 5-(benzyloxy)-6-((2S,3S,6S)-6-((R)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate

Guidance literature:: With triethyl borane; trimethylaluminum; oxygen; tri-n-butyl-tin hydride; In dichloromethane; at -78 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/jo2013884

Reference yield:

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

: 1333041-33-0
(2R,3S,4S,5S,6S)-methyl 5-(benzyloxy)-6-((2S,3S,6S)-6-((R)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 11 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: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 °C

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

8.2: -40 °C

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

10.1: titanium tetrachloride / dichloromethane / 1 h / -78 °C / Inert atmosphere

10.2: Saturated solution

11.1: triethyl borane; trimethylaluminum; oxygen; tri-n-butyl-tin hydride / dichloromethane / -78 °C / Inert atmosphere

With oxalyl dichloride; titanium(IV) trichloride isopropoxide; triethyl borane; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; trimethylaluminum; oxygen; tri-n-butyl-tin hydride; titanium tetrachloride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexanes; dichloromethane; cyclohexane; 4.1: Swern oxidation / 4.2: Swern oxidation / 5.1: Mukaiyama reaction / 10.1: 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

: 1333041-33-0
(2R,3S,4S,5S,6S)-methyl 5-(benzyloxy)-6-((2S,3S,6S)-6-((R)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 6 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: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 °C

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

3.2: -40 °C

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

5.1: titanium tetrachloride / dichloromethane / 1 h / -78 °C / Inert atmosphere

5.2: Saturated solution

6.1: triethyl borane; trimethylaluminum; oxygen; tri-n-butyl-tin hydride / dichloromethane / -78 °C / Inert atmosphere

With triethyl borane; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; oxygen; tri-n-butyl-tin hydride; titanium tetrachloride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In hexanes; dichloromethane; cyclohexane; 5.1: Mukaiyama reaction;
DOI:10.1021/jo2013884