(2R,3S,4S)-4-Benzyloxy-4-(1H-imidazol-4-yl)-butane-1,2,3-triol

Base Information

• Chemical Name: (2R,3S,4S)-4-Benzyloxy-4-(1H-imidazol-4-yl)-butane-1,2,3-triol
• CAS No.: 237749-86-9
• Molecular Formula: C₁₄H₁₈N₂O₄
• Molecular Weight: 278.308
• Mol file: 237749-86-9.mol

Synonyms:(2R,3S,4S)-4-Benzyloxy-4-(1H-imidazol-4-yl)-butane-1,2,3-triol

Chemical Property of (2R,3S,4S)-4-Benzyloxy-4-(1H-imidazol-4-yl)-butane-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-4-Benzyloxy-4-(1H-imidazol-4-yl)-butane-1,2,3-triol

There total 6 articles about (2R,3S,4S)-4-Benzyloxy-4-(1H-imidazol-4-yl)-butane-1,2,3-triol 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%

formamidine acetic acid (3473-63-0) + (2R,3R,4S,5R)-3-Benzyloxy-2,4,5,6-tetrahydroxy-hexanal (112670-07-2,65926-00-3) → (2R,3S,4S)-4-Benzyloxy-4-(1H-imidazol-4-yl)-butane-1,2,3-triol (237749-86-9)

Guidance literature:

With ammonia; at 80 ℃; for 48h; under 33752.7 Torr;

DOI:10.1016/S0040-4039(99)01003-5

Reference yield: 40.0%

formamidine acetic acid (3473-63-0) + (2R,3R,4R,5S,6R)-4-Benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2,3,5-triol → (2R,3S,4S)-4-Benzyloxy-4-(1H-imidazol-4-yl)-butane-1,2,3-triol (237749-86-9)

Guidance literature:

In ammonia; at 80 ℃; for 48h; under 33753.4 Torr;

DOI:10.1002/1099-0690(200104)2001:7<1335::AID-EJOC1335>3.0.CO;2-Z

Reference yield:

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose (14686-88-5) → (2R,3S,4S)-4-Benzyloxy-4-(1H-imidazol-4-yl)-butane-1,2,3-triol (237749-86-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / H₂ / 5percent Rh/Al₂O₃ / ethyl acetate / 0.75 h / 20 °C / 37503.8 Torr

2: Bu₄NI; NaOMe / tetrahydrofuran / 4.5 h / 0 - 20 °C

3: 5.30 g / 14 h / 50 °C

4: ethanol; H₂O / 4 h / 75 °C

5: 40 percent / liquid ammonia / 48 h / 80 °C / 33753.4 Torr

With hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; 5percent Rh/Al₂O₃; In tetrahydrofuran; ethanol; ammonia; water; ethyl acetate;

DOI:10.1002/1099-0690(200104)2001:7<1335::AID-EJOC1335>3.0.CO;2-Z

upstream raw materials:

formamidine acetic acid

(2R,3R,4S,5R)-3-Benzyloxy-2,4,5,6-tetrahydroxy-hexanal

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose

Downstream raw materials:

(6R,7S,8S)-8-Benzyloxy-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridine-6,7-diol