3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-manno-α-D-gluco-undecofuranose

Base Information

• Chemical Name: 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-manno-α-D-gluco-undecofuranose
• CAS No.: 258280-18-1
• Molecular Formula: C₂₇H₄₀O₁₀
• Molecular Weight: 524.609
• Mol file: 258280-18-1.mol

Synonyms:3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-manno-α-D-gluco-undecofuranose

Chemical Property of 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-manno-α-D-gluco-undecofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-manno-α-D-gluco-undecofuranose

There total 2 articles about 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-manno-α-D-gluco-undecofuranose 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: 59.0%

3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-arabino-α-D-gluco-undecos-7-ulo-1,4-furanose (258343-95-2) → 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-gluco-α-D-gluco-undecofuranose (149774-55-0) + 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-manno-α-D-gluco-undecofuranose (258280-18-1)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 - 20 ℃; for 1.25h;

DOI:10.1016/S0008-6215(99)00168-8

Reference yield:

(5R)-5-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-3-(1,2:3,4-di-O-isopropylidene-L-arabino-tetritol-1-yl)-4,5-dihydroisoxazole (149880-86-4) → 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-manno-α-D-gluco-undecofuranose (258280-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / H₂; boric acid / Raney-nickel / methanol; H₂O / 3 h

2: 32 percent / NaBH₄ / ethanol; H₂O / 20 °C

With sodium tetrahydroborate; hydrogen; boric acid; nickel; In methanol; ethanol; water; 1: Hydrogenolysis / 2: Reduction;

DOI:10.1016/S0008-6215(99)00168-8

Reference yield: 89.0%

2,2-dimethoxy-propane (77-76-9) + 3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-manno-α-D-gluco-undecofuranose (258280-18-1) → 3-O-benzyl-6-deoxy-1,2:5,7:8,9:10,11-tetra-O-isopropylidene-L-manno-α-D-gluco-undecofuranose

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 16h;

DOI:10.1016/S0008-6215(99)00168-8

upstream raw materials:

3-O-benzyl-6-deoxy-1,2:8,9:10,11-tri-O-isopropylidene-L-arabino-α-D-gluco-undecos-7-ulo-1,4-furanose

(5R)-5-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-3-(1,2:3,4-di-O-isopropylidene-L-arabino-tetritol-1-yl)-4,5-dihydroisoxazole