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

Base Information

Chemical Name:(2R,3R,4S)-methyl 3-(benzyloxy)-4-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-2-methylpentanoate
CAS No.:1333042-03-7
Molecular Formula:C₃₉H₅₄O₅Si
Molecular Weight:630.94
Hs Code.:

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

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

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

There total 9 articles about (2R,3R,4S)-methyl 3-(benzyloxy)-4-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-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: 78.0%

: 2,2,2-benzyltrichloroacetimidate

: 1333042-01-5
(2R,3R,4S)-methyl 4-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-3-hydroxy-2-methylpentanoate

: 1333042-03-7
(2R,3R,4S)-methyl 3-(benzyloxy)-4-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-2-methylpentanoate

Guidance literature:: With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; at 0 ℃;
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

: 1333042-03-7
(2R,3R,4S)-methyl 3-(benzyloxy)-4-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-2-methylpentanoate

Guidance literature:: Multi-step reaction with 9 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

With dmap; oxalyl dichloride; titanium(IV) trichloride isopropoxide; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; 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;
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

: 1333042-03-7
(2R,3R,4S)-methyl 3-(benzyloxy)-4-((2S,3S,6S)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-2-methylpentanoate

Guidance literature:: Multi-step reaction with 4 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

With dmap; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; cyclohexane;
DOI:10.1021/jo2013884