ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

Base Information

• Chemical Name: ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate
• CAS No.: 108788-48-3
• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.396
• Mol file: 108788-48-3.mol

Synonyms:ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

Chemical Property of ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

There total 4 articles about ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate 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: 90.0%

(3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (34370-89-3) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-lyxo-hept-5-enofuranuronate (108788-48-3,108788-49-4,136838-95-4,136839-11-7,145741-63-5,145741-64-6)

Guidance literature:

In acetonitrile; for 2h; Heating;

DOI:10.1021/jo00024a022

Reference yield: 80.0%

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-48-3)

Guidance literature:

In methanol; for 2h;

DOI:10.1016/0040-4039(91)80139-W

Reference yield: 64.0%

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (Z)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-48-3) + ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-49-4)

Guidance literature:

In acetonitrile; for 2h; Heating;

DOI:10.1039/a905440e

upstream raw materials:

(3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

ethyl (triphenylphosphoranylidene)acetate

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

ethyl bromoacetate

Downstream raw materials:

(3aS,5R,6S,6aR)-6-Benzyloxy-5-dimethoxymethyl-tetrahydro-furo[3,2-b]furan-2-one

(Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-eno-1,4-furanose

ethyl [5-amino-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene]-heptofuranuronate

ethyl [(1R,2R,3S,4R,5RS)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-{N³-(4-chlorophenyl)-1-ureidyl}-1,4-heptofuranos-5-yl]uronoate