3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose

Base Information

• Chemical Name: 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose
• CAS No.: 20715-20-2
• Molecular Formula: C₂₁H₂₂O₅
• Molecular Weight: 354.403
• Mol file: 20715-20-2.mol

Synonyms:3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose

Chemical Property of 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose

There total 4 articles about 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose 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: 95.0%

3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-L-ido-pentofuranose (18439-42-4,18439-43-5) → 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose (20715-20-2)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 3h; Reflux;

DOI:10.1016/j.bmcl.2013.08.069

Reference yield: 82.0%

((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-phenyl-methanol (18439-42-4,18439-43-5) → 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose (20715-20-2)

Guidance literature:

With dipyridinium dichromate; 4 A molecular sieve; acetic acid; In dichloromethane; for 6h;

DOI:10.1016/j.tet.2006.09.005

Reference yield:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-xylo-pent-5-ulo-furanose (20715-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1: periodic acid / ethyl acetate / 1.5 h / 20 °C

2: periodic acid / toluene; tetrahydrofuran / 4.5 h / 0 °C / Inert atmosphere

3: pyridinium chlorochromate / dichloromethane / 3 h / Reflux

With periodic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;

DOI:10.1016/j.bmcl.2013.08.069

upstream raw materials:

((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-phenyl-methanol

3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-L-ido-pentofuranose

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

3-O-benzyl-1,2-O-isopropylidene-β-L-arabino-pentodialdo-1,4-furanose

Downstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose

3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-L-ido-pentofuranose

5-(1,3-bis(benzyloxy)-2-hydroxy-3-phenylpropyl)-4-hydroxy-dihydro-furan-2-one

(2S,3R,4R)-2,4-bis(benzyloxy)-3-formyloxy-4-phenyl-1-butanal