2-((2S,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-Methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethanol

Base Information

• Chemical Name: 2-((2S,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-Methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethanol
• CAS No.: 876152-53-3
• Molecular Formula: C₂₀H₃₆O₄
• Molecular Weight: 340.503
• Mol file: 876152-53-3.mol

Synonyms:2-((2S,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-Methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethanol

Chemical Property of 2-((2S,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-Methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2S,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-Methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethanol

There total 1 articles about 2-((2S,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-Methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethanol 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:

5-(1-hydroxyethyl)dihydrofuran-2(3H)-one (27610-27-1,105814-63-9) → 2-((2S,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-Methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethanol (876152-53-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 70 percent / DIAD; PPh₃ / toluene / 16 h / 20 °C

2.1: 94 percent / KOH / ethanol / 2 h / 60 °C

3.1: 77 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

4.1: LDA / tetrahydrofuran / 2 h / -78 °C

4.2: tetrahydrofuran / 2 h / -78 °C

5.1: DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

6.1: BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

7.1: TBAF / tetrahydrofuran / 16 h / 20 °C

8.1: 81 percent / NaH / dimethylformamide / 2 h / 20 °C

9.1: 65 percent / TBAF

With 1H-imidazole; potassium hydroxide; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Mitsunobu reaction;

DOI:10.1055/s-2005-918486

Reference yield:

2-((2S,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-Methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethanol (876152-53-3) → tetronasin sodium salt (149298-89-5)

Guidance literature:

Multi-step reaction with 11 steps

1: DMSO, (COCl)2, Et₃N / CH₂Cl₂

2: NaClO₂

4: 1.) LDA / 1.) THF, -100 deg C, 2.) -95 deg C, 30 min

5: pyridine, DMAP

6: DBU / Ambient temperature

7: 34 percent / acetone / 0 °C / Irradiation

8: (i-Bu)2AlH (DIBALH) / toluene

9: imidazole

10: 80 percent / ZrCl₄ / CH₂Cl₂ / 0.25 h / 0 °C

11: 1.) n-Bu₄NF (TBAF), 2.) HF / 1.) THF, 2.) CH₃CN

With pyridine; 1H-imidazole; dmap; sodium chlorite; oxalyl dichloride; hydrogen fluoride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; zirconium(IV) chloride; In dichloromethane; acetone; toluene;

DOI:10.1016/S0040-4039(00)60377-5

Reference yield:

2-((2S,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-Methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-ethanol (876152-53-3) → C42H72O9Si (149298-91-9)

Guidance literature:

Multi-step reaction with 10 steps

1: DMSO, (COCl)2, Et₃N / CH₂Cl₂

2: NaClO₂

4: 1.) LDA / 1.) THF, -100 deg C, 2.) -95 deg C, 30 min

5: pyridine, DMAP

6: DBU / Ambient temperature

7: 34 percent / acetone / 0 °C / Irradiation

8: (i-Bu)2AlH (DIBALH) / toluene

9: imidazole

10: 80 percent / ZrCl₄ / CH₂Cl₂ / 0.25 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium chlorite; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; zirconium(IV) chloride; In dichloromethane; acetone; toluene;

DOI:10.1016/S0040-4039(00)60377-5

upstream raw materials:

5-(1-hydroxyethyl)dihydrofuran-2(3H)-one

Downstream raw materials:

tetronasin sodium salt

(S)-2-{(1S,2S,6R)-2-[(E)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-propenyl]-6-methyl-cyclohexyl}-propionaldehyde

C₄₂H₇₂O₉Si

(E)-3-[(1S,2S,3R)-2-((S)-Cyano-methyl-methyl)-3-methyl-cyclohexyl]-2-((2R,3R,6S)-6-{(E)-(S)-3-[(2R,3S,5R)-5-((S)-1-methoxy-ethyl)-3-methyl-tetrahydro-furan-2-yl]-but-1-enyl}-3-methyl-tetrahydro-pyran-2-yl)-acrylic acid methyl ester