3,6-anhydro-7-O-(tert-butyldiphenylsilyl)-5-O-cinnamoyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone

Base Information

• Chemical Name: 3,6-anhydro-7-O-(tert-butyldiphenylsilyl)-5-O-cinnamoyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone
• CAS No.: 1233484-19-9
• Molecular Formula: C₃₈H₃₈O₆Si
• Molecular Weight: 618.802
• Mol file: 1233484-19-9.mol

Synonyms:3,6-anhydro-7-O-(tert-butyldiphenylsilyl)-5-O-cinnamoyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone

Chemical Property of 3,6-anhydro-7-O-(tert-butyldiphenylsilyl)-5-O-cinnamoyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,6-anhydro-7-O-(tert-butyldiphenylsilyl)-5-O-cinnamoyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone

There total 1 articles about 3,6-anhydro-7-O-(tert-butyldiphenylsilyl)-5-O-cinnamoyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone 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: 65.0%

cycl-isopropylidene malonate (2033-24-1) + 5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-5-C-phenyl-D-glucofuranose (1233484-18-8) → 3,6-anhydro-7-O-(tert-butyldiphenylsilyl)-5-O-cinnamoyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone (1233484-19-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 47 ℃; for 63h;

DOI:10.1016/j.tetlet.2010.04.114

Reference yield: 56.0%

3,6-anhydro-7-O-(tert-butyldiphenylsilyl)-5-O-cinnamoyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone (1233484-19-9) → (2R,3S,3aS,6aR)-2-((R)-hydroxy(phenyl)methyl)-5-oxo-hexahydrofuro[3,2-b]furan-3-yl cinnamate (918907-24-1)

Guidance literature:

With thionyl chloride; In methanol; at 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2010.04.114

Reference yield: 43.0%

3,6-anhydro-7-O-(tert-butyldiphenylsilyl)-5-O-cinnamoyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone (1233484-19-9) → (R)-((2S,3S,3aR,6aR)-3-hydroxy-5-oxo-hexahydrofuro[3,2-b]furan-2-yl)(phenyl)methyl cinnamate + (2R,3S,3aS,6aR)-2-((R)-hydroxy(phenyl)methyl)-5-oxo-hexahydrofuro[3,2-b]furan-3-yl cinnamate (918907-24-1)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 144h;

DOI:10.1016/j.tetlet.2010.04.114

upstream raw materials:

cycl-isopropylidene malonate

5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-5-C-phenyl-D-glucofuranose

Downstream raw materials:

(2R,3S,3aS,6aR)-2-((R)-hydroxy(phenyl)methyl)-5-oxo-hexahydrofuro[3,2-b]furan-3-yl cinnamate