(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-1-ol

Base Information

• Chemical Name: (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-1-ol
• CAS No.: 157220-49-0
• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.391
• Mol file: 157220-49-0.mol

Synonyms:(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-1-ol

Chemical Property of (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-1-ol

There total 17 articles about (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-1-ol 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:

(E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol (179945-16-5) → (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-1-ol (157220-49-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / molecular sieves 4A, titanium tetraisopropoxide, (+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 1.5 h / -23 °C

2: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -23 -> 4 deg C

3: 100 percent / pyridine / 5 h / 0 °C

4: 91 percent / dimethylsulfoxide / 2.5 h / 50 °C

6: 100 percent / sodium, liquid ammonia / tetrahydrofuran / 0.5 h / -78 °C

7: 100 percent / imidazole / dimethylformamide / 1.3 h / 0 °C

8: 1.) NaH, 2.) Bu₄NF / 1.) DMF, mineral oil, 0 -> 23 deg C, 2.) THF, 23 deg C, 13 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; sodium; sodium hydride; (+)-Weinsaeure-diethylester; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo9606113

Reference yield:

(2R,3R,4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hexane-1,3-diol (157220-46-7) → (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-1-ol (157220-49-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / pyridine / 5 h / 0 °C

2: 91 percent / dimethylsulfoxide / 2.5 h / 50 °C

4: 100 percent / sodium, liquid ammonia / tetrahydrofuran / 0.5 h / -78 °C

5: 100 percent / imidazole / dimethylformamide / 1.3 h / 0 °C

6: 1.) NaH, 2.) Bu₄NF / 1.) DMF, mineral oil, 0 -> 23 deg C, 2.) THF, 23 deg C, 13 h

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; ammonia; sodium; sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo9606113

Reference yield:

<2S,3S>-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>-N-methoxy>-N,2-dimethyl-4-phenylmethoxybutanamide (157220-45-6) → (2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-1-ol (157220-49-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 99 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

2: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, -78 -> 0 deg C

3: 97 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

4: 96 percent / molecular sieves 4A, titanium tetraisopropoxide, (+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 1.5 h / -23 °C

5: 1.) copper(I) iodide / 1.) diethyl ether, -23 deg C, 30 min, 2.) diethyl ether, -23 -> 4 deg C

6: 100 percent / pyridine / 5 h / 0 °C

7: 91 percent / dimethylsulfoxide / 2.5 h / 50 °C

9: 100 percent / sodium, liquid ammonia / tetrahydrofuran / 0.5 h / -78 °C

10: 100 percent / imidazole / dimethylformamide / 1.3 h / 0 °C

11: 1.) NaH, 2.) Bu₄NF / 1.) DMF, mineral oil, 0 -> 23 deg C, 2.) THF, 23 deg C, 13 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; sodium; sodium hydride; diisobutylaluminium hydride; (+)-Weinsaeure-diethylester; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo9606113

upstream raw materials:

[(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butoxy]-tert-butyl-diphenyl-silane

benzyl bromide

(2S,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butan-2-ol

(2S,3S)-3-((2R,3R)-5-Methoxy-3-methyl-tetrahydro-furan-2-yl)-butane-1,2-diol

Downstream raw materials:

(2R,3R)-2-[(1S,2R,5S,6S,7R,8S)-10-Benzenesulfonyl-2-(3,4-dimethoxy-benzyloxymethoxy)-1,5,7-trimethyl-6,8-bis-triethylsilanyloxy-decyl]-5-methoxy-3-methyl-tetrahydro-furan

(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde