1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxy-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxy-D-arabino-hex-1-enitol
• CAS No.: 111002-90-5
• Molecular Formula: C₂₀H₂₂O₃
• Molecular Weight: 310.393
• Mol file: 111002-90-5.mol

Synonyms:1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxy-D-arabino-hex-1-enitol

Chemical Property of 1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxy-D-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxy-D-arabino-hex-1-enitol

There total 5 articles about 1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxy-D-arabino-hex-1-enitol 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: 86.5%

benzyl bromide (100-39-0) + (2R,3S,4R)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diol (78086-61-0) → 1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxy-D-arabino-hex-1-enitol (111002-90-5)

Guidance literature:

(2R,3S,4R)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diol; With sodium hydride; In N,N-dimethyl-formamide; for 0.25h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; at 30 ℃; for 4h; Concentration; Temperature; Inert atmosphere;

Reference yield: 83.0%

benzyl bromide (100-39-0) + 3,4-di-O-acetyl-D-rhamnal (76739-66-7) → 1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxy-D-arabino-hex-1-enitol (111002-90-5)

Guidance literature:

3,4-di-O-acetyl-D-rhamnal; With sodium methylate; In methanol; at 0 ℃; for 3h;

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1055/s-0037-1611916

Reference yield:

(2R,3S,4R)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diol (78086-61-0) → 1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxy-D-arabino-hex-1-enitol (111002-90-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / imidazole / dimethylformamide

2: 1.) NaH / 2.) tetrabutylammonium iodide / 1.) DMF, THF, room temperature, 1 h, 2.) 6 h

With 1H-imidazole; sodium hydride; tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(93)84204-J

upstream raw materials:

benzyl bromide

(2R,3S,4R)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diol

1,5-anhydro-3-O-tert-butyldiphenylsilyl-2,6-dideoxy-D-arabino-hex-1-enitol

3,4-di-O-acetyl-D-rhamnal

Downstream raw materials:

(2R,3R,4R,6S)-4-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-3-ol

Benzoic acid (2R,3R,4R,6S)-4-((2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester

Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yl ester