methyl 2,4-anhydro-3-O-benzoyl-5-bromo-5,6-dideoxy-D-gulonate

Base Information

• Chemical Name: methyl 2,4-anhydro-3-O-benzoyl-5-bromo-5,6-dideoxy-D-gulonate
• CAS No.: 807617-76-1
• Molecular Formula: C₁₄H₁₅BrO₅
• Molecular Weight: 343.174
• Mol file: 807617-76-1.mol

Synonyms:methyl 2,4-anhydro-3-O-benzoyl-5-bromo-5,6-dideoxy-D-gulonate

Chemical Property of methyl 2,4-anhydro-3-O-benzoyl-5-bromo-5,6-dideoxy-D-gulonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,4-anhydro-3-O-benzoyl-5-bromo-5,6-dideoxy-D-gulonate

There total 1 articles about methyl 2,4-anhydro-3-O-benzoyl-5-bromo-5,6-dideoxy-D-gulonate 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: 86.0%

methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate (322726-61-4) → methyl 2,4-anhydro-3-O-benzoyl-5-bromo-5,6-dideoxy-D-gulonate (807617-76-1)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; at 60 ℃; for 22h;

DOI:10.1016/j.tetasy.2004.08.023

Reference yield: 61.0%

methyl 2,4-anhydro-3-O-benzoyl-5-bromo-5,6-dideoxy-D-gulonate (807617-76-1) → methyl 2,4-anhydro-5-azido-3-O-benzoyl-5-deoxy-L-rhamnonate (807617-78-3)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 85 ℃; for 17h;

DOI:10.1016/j.tetasy.2004.08.023

Reference yield:

methyl 2,4-anhydro-3-O-benzoyl-5-bromo-5,6-dideoxy-D-gulonate (807617-76-1) → methyl 2,4-anhydro-5-azido-3-O-tert-butyldimethylsilyl-5,6-dideoxy-L-altronate

Guidance literature:

Multi-step reaction with 6 steps

1: 61 percent / sodium azide / dimethylsulfoxide / 17 h / 85 °C

2: sodium hydroxide / tetrahydrofuran; H₂O / 20 °C

3: 1.40 g / hydrochloric acid / tetrahydrofuran; H₂O / 24 h

4: 100 percent / pyridine / CH₂Cl₂ / -78 - 0 °C

5: 99 percent / caesium trifluoroacetate / butan-2-one / 3.5 h / 60 °C

6: 99 percent / pyridine / CH₂Cl₂ / -20 - 0 °C

With pyridine; hydrogenchloride; sodium hydroxide; sodium azide; cesium trifluoroacetate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; butanone;

DOI:10.1016/j.tetasy.2004.08.023

upstream raw materials:

methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate

Downstream raw materials:

methyl 2,4-anhydro-5-azido-3-O-benzoyl-5-deoxy-L-rhamnonate