1,6-anhydro-3-O-benzoyl-2,4-dideoxy-β-D-threo-hexopyranoside

Base Information

• Chemical Name: 1,6-anhydro-3-O-benzoyl-2,4-dideoxy-β-D-threo-hexopyranoside
• CAS No.: 146431-48-3
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.252
• Mol file: 146431-48-3.mol

Synonyms:1,6-anhydro-3-O-benzoyl-2,4-dideoxy-β-D-threo-hexopyranoside

Chemical Property of 1,6-anhydro-3-O-benzoyl-2,4-dideoxy-β-D-threo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-3-O-benzoyl-2,4-dideoxy-β-D-threo-hexopyranoside

There total 4 articles about 1,6-anhydro-3-O-benzoyl-2,4-dideoxy-β-D-threo-hexopyranoside 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: 80.0%

(1R,3S,5S)-6,8-dioxabicyclo[3.2.1]octan-3-ol (14241-58-8) + benzoyl chloride (98-88-4) → 1,6-anhydro-3-O-benzoyl-2,4-dideoxy-β-D-threo-hexopyranoside (146431-48-3)

Guidance literature:

With pyridine; dmap; for 12h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80508-1

Reference yield: 70.0%

(1R,3S,5S)-6,8-dioxabicyclo[3.2.1]octan-3-ol (14241-58-8) + benzoic acid (65-85-0,8013-63-6) → 1,6-anhydro-3-O-benzoyl-2,4-dideoxy-β-D-threo-hexopyranoside (146431-48-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/0040-4039(92)88123-M

Reference yield:

1,6-anhydro-2,4-bis-O-phenoxythiocarbonyl-D-glucose (141810-56-2) → 1,6-anhydro-3-O-benzoyl-2,4-dideoxy-β-D-threo-hexopyranoside (146431-48-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / tris(trimethylsilyl)silane, AIBN / toluene / 1.3 h / Heating

2: 70 percent / DEAD, Ph₃P / tetrahydrofuran / 2 h / Ambient temperature

With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene;

DOI:10.1016/0040-4039(92)88123-M

upstream raw materials:

(1R,3S,5S)-6,8-dioxabicyclo[3.2.1]octan-3-ol

benzoyl chloride

benzoic acid

1,6-anhydro-2,4-bis-O-phenoxythiocarbonyl-D-glucose

Downstream raw materials:

Methyl-3-O-benzoyl-2,4-dideoxy-β-D-threo-hexopyranoside

Methyl-3-O-benzoyl-2,4-dideoxy-α-D-threo-hexopyranoside

Benzoic acid (2S,4S,6R)-2-formyl-6-methoxy-tetrahydro-pyran-4-yl ester

Benzoic acid (2S,4S,6S)-2-formyl-6-methoxy-tetrahydro-pyran-4-yl ester