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

Base Information

• Chemical Name: (2S,3R)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde
• CAS No.: 76859-48-8
• Molecular Formula: C₂₅H₃₂O₆
• Molecular Weight: 428.525
• Mol file: 76859-48-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (2S,3R)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde 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:

(2S,3R)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-3-(ethylsulfanyl-methylsulfanyl-methyl)-5-methoxy-tetrahydro-furan → (2S,3R)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde (76859-48-8)

Guidance literature:

With cadmium(II) carbonate; mercury dichloride; In water; acetone; at 20 ℃; for 2h; Yield given;

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) → (2S,3R)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde (76859-48-8)

Guidance literature:

Multi-step reaction with 10 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

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 → (2S,3R)-2-((1S,2R)-2,4-Bis-benzyloxy-1-methoxy-butyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde (76859-48-8)

Guidance literature:

Multi-step reaction with 9 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

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:

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

(4R,5S)-5-((1S,2R)-2,4-Dihydroxy-1-methoxy-butyl)-4-(ethylsulfanyl-methylsulfanyl-methyl)-dihydro-furan-2-one

(E)-3-[(4S,5S,6R)-5-Methoxy-6-(2-methoxymethoxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acrylic acid methyl ester

Downstream raw materials:

(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