(1R,2R,3S,4R)-methyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate

Base Information

• Chemical Name: (1R,2R,3S,4R)-methyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate
• CAS No.: 72277-35-1
• Molecular Formula: C₁₈H₂₂O₆
• Molecular Weight: 334.369
• Mol file: 72277-35-1.mol

Synonyms:(1R,2R,3S,4R)-methyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate

Chemical Property of (1R,2R,3S,4R)-methyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4R)-methyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate

There total 7 articles about (1R,2R,3S,4R)-methyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate 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%

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → (1R,2R,3S,4R)-methyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate (72277-35-1)

Guidance literature:

In benzene; at 20 ℃;

DOI:10.1016/j.carres.2020.108080

Reference yield: 81.0%

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → (1R,2R,3S,4R)-methyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate (72277-35-1)

Guidance literature:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose; With periodic acid; In ethyl acetate; for 3h;

methyl (triphenylphosphoranylidene)acetate; In tetrahydrofuran;

DOI:10.1016/S0040-4039(03)00817-7

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (350255-13-9) → (1R,2R,3S,4R)-methyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]heptfuran-5-enuronate (72277-35-1)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 24 °C

2: acetic acid; water / 3 h / 55 °C

3: sodium periodate / dichloromethane; water / 1.83 h / 30 °C

4: benzene / 20 °C

With sodium periodate; water; sodium hydride; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/j.carres.2020.108080

upstream raw materials:

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

methyl (triphenylphosphoranylidene)acetate

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

3-O-benzyl-5,6-dideoxy-1,2-dideoxy-1,2-O-isopropylidene-α-D-xylohept-5-eno-1,4-furanose