ethyl (+)-(R)-2-{(2S,3S,6S)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate

Base Information

• Chemical Name: ethyl (+)-(R)-2-{(2S,3S,6S)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate
• CAS No.: 1370254-42-4
• Molecular Formula: C₂₁H₃₂O₄
• Molecular Weight: 348.483

Synonyms:ethyl (+)-(R)-2-{(2S,3S,6S)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate

Chemical Property of ethyl (+)-(R)-2-{(2S,3S,6S)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (+)-(R)-2-{(2S,3S,6S)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate

There total 10 articles about ethyl (+)-(R)-2-{(2S,3S,6S)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate 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: 40.0%

ethyl (+)-(S)-2-{(2S,3S,6S)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}-2-iodopropanoate (1370254-38-8) → ethyl (+)-(R)-2-{(2S,3S,6S)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate (1370254-42-4)

Guidance literature:

ethyl (+)-(S)-2-{(2S,3S,6S)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}-2-iodopropanoate; With magnesium bromide diethyl etherate; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

With triethyl borane; tri-n-butyl-tin hydride; In dichloromethane; at -78 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1055/s-0031-1289661

Reference yield:

methyl (2R)-3-(benzyloxy)-2-methylpropanoate (56850-58-9,59965-24-1,74924-27-9,112068-34-5) → ethyl (+)-(R)-2-{(2S,3S,6S)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate (1370254-42-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: 0.25 h / -78 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

2.2: 18 h / 20 °C / Inert atmosphere

3.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1 h / -40 °C / Inert atmosphere

3.2: -40 °C / Inert atmosphere

4.1: pyridine; palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 0 °C / Inert atmosphere

6.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 °C / Inert atmosphere

7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

8.1: toluene / 18 h / 20 °C / Reflux; Inert atmosphere

9.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 °C / Inert atmosphere

10.1: iodine; silver trifluoromethanesulfonate; sodium hydrogencarbonate / tetrahydrofuran / 20 °C / Inert atmosphere

11.1: magnesium bromide diethyl etherate / dichloromethane / 1 h / 0 °C / Inert atmosphere

11.2: air / -78 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; n-butyllithium; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; iodine; silver trifluoromethanesulfonate; magnesium bromide diethyl etherate; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 2.1: Horner-Wadsworth-Emmons olefination / 2.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1055/s-0031-1289661

Reference yield:

dimethyl (-)-(R)-4-(benzyloxy)-3-methyl-2-oxobutylphosphonate (1370254-18-4) → ethyl (+)-(R)-2-{(2S,3S,6S)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate (1370254-42-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: lithium hydroxide monohydrate / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

1.2: 18 h / 20 °C / Inert atmosphere

2.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1 h / -40 °C / Inert atmosphere

2.2: -40 °C / Inert atmosphere

3.1: pyridine; palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 0 °C / Inert atmosphere

5.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

7.1: toluene / 18 h / 20 °C / Reflux; Inert atmosphere

8.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 °C / Inert atmosphere

9.1: iodine; silver trifluoromethanesulfonate; sodium hydrogencarbonate / tetrahydrofuran / 20 °C / Inert atmosphere

10.1: magnesium bromide diethyl etherate / dichloromethane / 1 h / 0 °C / Inert atmosphere

10.2: air / -78 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; iodine; silver trifluoromethanesulfonate; magnesium bromide diethyl etherate; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1055/s-0031-1289661

upstream raw materials:

(+)-(5S,8S)-5-[(R)-1-(benzyloxy)propan-2-yl]-2,2,3,3,8,11,11,12,12-nonamethyl-4,10-dioxa-3,11-disilatridecane

(-)-(2S,5S,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptan-1-ol

(+)-(2S,5S,6R)-7-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,6-dimethylheptanal

ethyl (+)-(4S,7S,8R,E)-9-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-2,4,8-trimethylnon-2-enoate

Downstream raw materials:

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

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

(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

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 1370254-42-4 ethyl (+)-(R)-2-{(2S,3S,6S)-6-[(R)-1-(benzyloxy)propan-2-yl]-3-methyltetrahydro-2H-pyran-2-yl}propanoate

Send

Send

Metric Ton KG G Pound L ML

Send

Send