(Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one

Base Information

• Chemical Name: (Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one
• CAS No.: 76859-49-9
• Molecular Formula: C₂₉H₃₈O₆
• Molecular Weight: 482.617
• Mol file: 76859-49-9.mol

Synonyms:(Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one

Chemical Property of (Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one

There total 11 articles about (Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one 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: 91.0%

3-(triphenylphosphoranylidene)butan-2-one (26487-92-3) + (2S,3R)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde (76859-48-8) → (Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one (76859-49-9)

Guidance literature:

In toluene; at 105 ℃; for 48h;

DOI:10.1016/S0040-4039(00)78621-7

Reference yield:

5-deoxy-3-O-methyl-1,2-O-(methylethylidene)-α-D-xylo-hexo-furanose (62853-46-7) → (Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one (76859-49-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 6N H₂SO₄ / 3 h / 20 °C

2: 75 percent / methyl acetate / 15 h / 50 °C

3: N,N-diisopropylethylamine / CHCl₃ / 72 h / 28 °C

4: TsOH / dimethylformamide / 2 h / 20 °C

5: 79 percent / butyllithium / hexane; tetrahydrofuran / 1.) -78 deg C, 2.5 h, 2.) 0 deg C, 1 h

6: 78 percent / BF₃ / diethyl ether / 15 h / 20 °C

7: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C

8: 72 percent / Amberlyst 15 / 3 h / 20 °C

9: NaH / dimethylformamide / 2 h / 20 °C

10: CdCO₃, HgCl₂ / acetone; H₂O / 2 h / 20 °C

11: 91 percent / toluene / 48 h / 105 °C

With n-butyllithium; Amberlyst 15; cadmium(II) carbonate; sulfuric acid; boron trifluoride; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; mercury dichloride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; chloroform; acetic acid methyl ester; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/S0040-4039(00)78621-7

Reference yield:

(2S,3R,4R,5R)-5-(2-Hydroxy-ethyl)-4-methoxy-tetrahydro-furan-2,3-diol → (Z)-4-[(2S,3S)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-yl]-3-methyl-but-3-en-2-one (76859-49-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 75 percent / methyl acetate / 15 h / 50 °C

2: N,N-diisopropylethylamine / CHCl₃ / 72 h / 28 °C

3: TsOH / dimethylformamide / 2 h / 20 °C

4: 79 percent / butyllithium / hexane; tetrahydrofuran / 1.) -78 deg C, 2.5 h, 2.) 0 deg C, 1 h

5: 78 percent / BF₃ / diethyl ether / 15 h / 20 °C

6: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C

7: 72 percent / Amberlyst 15 / 3 h / 20 °C

8: NaH / dimethylformamide / 2 h / 20 °C

9: CdCO₃, HgCl₂ / acetone; H₂O / 2 h / 20 °C

10: 91 percent / toluene / 48 h / 105 °C

With n-butyllithium; Amberlyst 15; cadmium(II) carbonate; boron trifluoride; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; mercury dichloride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; chloroform; acetic acid methyl ester; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/S0040-4039(00)78621-7

upstream raw materials:

3-(triphenylphosphoranylidene)butan-2-one

(2S,3R)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde

5-deoxy-3-O-methyl-1,2-O-(methylethylidene)-α-D-xylo-hexo-furanose

(3R,4S)-4-[(2S,3R)-3-(Ethylsulfanyl-methylsulfanyl-methyl)-5-methoxy-tetrahydro-furan-2-yl]-4-methoxy-butane-1,3-diol