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

Base Information

Chemical Name:(2R,3R,4S)-methyl 4-((2S,3S,6S)-6-((R)-1-(benzyloxy)-propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2-methylpentanoate
CAS No.:1333041-12-5
Molecular Formula:C₂₃H₃₆O₅
Molecular Weight:392.536
Hs Code.:

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

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

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

There total 18 articles about (2R,3R,4S)-methyl 4-((2S,3S,6S)-6-((R)-1-(benzyloxy)-propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2-methylpentanoate 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: 77.0%

: (+/-)-(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

: 1333041-12-5
(2R,3R,4S)-methyl 4-((2S,3S,6S)-6-((R)-1-(benzyloxy)-propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2-methylpentanoate

Guidance literature:: (+/-)-(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; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1.5h; Inert atmosphere;

With triethyl borane; 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:

: 1333041-05-6
(+)-(R)-2-((2S,3S,6S)-6-((R)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)propanal

: 1333041-12-5
(2R,3R,4S)-methyl 4-((2S,3S,6S)-6-((R)-1-(benzyloxy)-propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2-methylpentanoate

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: Saturated solution

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

2.2: -78 °C / Inert atmosphere

With titanium(IV) trichloride isopropoxide; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1.1: Mukaiyama reaction;
DOI:10.1021/jo2013884

Reference yield:

: 1333041-91-0
(+)-(S)-2-((2S,3S,6S)-6-((R)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)propan-1-ol

: 1333041-12-5
(2R,3R,4S)-methyl 4-((2S,3S,6S)-6-((R)-1-(benzyloxy)-propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2-methylpentanoate

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 1 h / -78 °C / Inert atmosphere

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

2.2: Saturated solution

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

3.2: -78 °C / Inert atmosphere

With oxalyl dichloride; titanium(IV) trichloride isopropoxide; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Mukaiyama reaction;
DOI:10.1021/jo2013884