(3S,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

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Chemical Name:(3S,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
CAS No.:1333041-10-3
Molecular Formula:C₂₃H₃₅BrO₅
Molecular Weight:471.432
Hs Code.:

Synonyms:(3S,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

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Chemical Property of (3S,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

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Technology Process of (3S,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

There total 5 articles about (3S,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 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:

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

: 199384-57-1
methyl ((2-bromo-1-methoxyprop-1-en-1-yl)oxy)trimethylsilane

: 1333041-10-3
(3S,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

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h; 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

: 1333041-10-3
(3S,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

Guidance literature:: Multi-step reaction with 5 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: boron trifluoride diethyl etherate / dichloromethane / 1 h / -78 °C / Inert atmosphere

With oxalyl dichloride; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; hexanes; dichloromethane; cyclohexane; 4.1: Swern oxidation / 4.2: Swern oxidation / 5.1: 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

: 1333041-10-3
(3S,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

Guidance literature:: Multi-step reaction with 4 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: boron trifluoride diethyl etherate / dichloromethane / 1 h / -78 °C / Inert atmosphere

With oxalyl dichloride; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; cyclohexane; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Mukaiyama reaction;
DOI:10.1021/jo2013884