3-O-benzyl-(Z)-5,6-dehydro-5,6,7,8,9,10,11,12,13,14,15,16,17,18-tetradecadeoxy-1,2-O-isopropylidene-α-D-xylo-octadecofuranose

Base Information

• Chemical Name: 3-O-benzyl-(Z)-5,6-dehydro-5,6,7,8,9,10,11,12,13,14,15,16,17,18-tetradecadeoxy-1,2-O-isopropylidene-α-D-xylo-octadecofuranose
• CAS No.: 105265-47-2
• Molecular Formula: C₂₈H₄₄O₄
• Molecular Weight: 444.655
• Mol file: 105265-47-2.mol

Synonyms:3-O-benzyl-(Z)-5,6-dehydro-5,6,7,8,9,10,11,12,13,14,15,16,17,18-tetradecadeoxy-1,2-O-isopropylidene-α-D-xylo-octadecofuranose

Chemical Property of 3-O-benzyl-(Z)-5,6-dehydro-5,6,7,8,9,10,11,12,13,14,15,16,17,18-tetradecadeoxy-1,2-O-isopropylidene-α-D-xylo-octadecofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-(Z)-5,6-dehydro-5,6,7,8,9,10,11,12,13,14,15,16,17,18-tetradecadeoxy-1,2-O-isopropylidene-α-D-xylo-octadecofuranose

There total 5 articles about 3-O-benzyl-(Z)-5,6-dehydro-5,6,7,8,9,10,11,12,13,14,15,16,17,18-tetradecadeoxy-1,2-O-isopropylidene-α-D-xylo-octadecofuranose 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:

n-tridecyltriphenylphosphonium bromide (13266-02-9) + 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → C28H44O4 + 3-O-benzyl-(Z)-5,6-dehydro-5,6,7,8,9,10,11,12,13,14,15,16,17,18-tetradecadeoxy-1,2-O-isopropylidene-α-D-xylo-octadecofuranose (105265-47-2)

Guidance literature:

n-tridecyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.5h;

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose; In tetrahydrofuran; at 0 ℃; for 4h; optical yield given as %de;

DOI:10.1016/j.tetlet.2011.09.045

Reference yield:

benzyl bromide (100-39-0) → C28H44O4 + 3-O-benzyl-(Z)-5,6-dehydro-5,6,7,8,9,10,11,12,13,14,15,16,17,18-tetradecadeoxy-1,2-O-isopropylidene-α-D-xylo-octadecofuranose (105265-47-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride

2.1: periodic acid / ethyl acetate / 2 h

3.1: n-butyllithium / tetrahydrofuran / 0.5 h / 0 °C

3.2: 4 h / 0 °C

With n-butyllithium; sodium hydride; periodic acid; In tetrahydrofuran; ethyl acetate; 3.2: Wittig reaction;

DOI:10.1016/j.tetlet.2011.09.045

Reference yield:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → C28H44O4 + 3-O-benzyl-(Z)-5,6-dehydro-5,6,7,8,9,10,11,12,13,14,15,16,17,18-tetradecadeoxy-1,2-O-isopropylidene-α-D-xylo-octadecofuranose (105265-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: periodic acid / ethyl acetate / 2 h

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / 0 °C

2.2: 4 h / 0 °C

With n-butyllithium; periodic acid; In tetrahydrofuran; ethyl acetate; 2.2: Wittig reaction;

DOI:10.1016/j.tetlet.2011.09.045

upstream raw materials:

n-tridecyltriphenylphosphonium bromide

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

benzyl bromide

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