5-O-benzyl-1,2-O-isopropylidine-3-O-(2-propyn-1-yl)-α-D-xylofuranose

Base Information

• Chemical Name: 5-O-benzyl-1,2-O-isopropylidine-3-O-(2-propyn-1-yl)-α-D-xylofuranose
• CAS No.: 1612222-32-8
• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.37
• Mol file: 1612222-32-8.mol

Synonyms:5-O-benzyl-1,2-O-isopropylidine-3-O-(2-propyn-1-yl)-α-D-xylofuranose

Chemical Property of 5-O-benzyl-1,2-O-isopropylidine-3-O-(2-propyn-1-yl)-α-D-xylofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-benzyl-1,2-O-isopropylidine-3-O-(2-propyn-1-yl)-α-D-xylofuranose

There total 6 articles about 5-O-benzyl-1,2-O-isopropylidine-3-O-(2-propyn-1-yl)-α-D-xylofuranose 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: 83.0%

benzyl bromide (100-39-0) + [(3aR,5R,6S,6aR)-2,2-dimethyl-6-(prop-2-yn-1-yloxy)tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]methanol (308279-03-0) → 5-O-benzyl-1,2-O-isopropylidine-3-O-(2-propyn-1-yl)-α-D-xylofuranose (1612222-32-8)

Guidance literature:

[(3aR,5R,6S,6aR)-2,2-dimethyl-6-(prop-2-yn-1-yloxy)tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]methanol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

DOI:10.1002/jhet.2845

Reference yield:

5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (23202-83-7,2592-42-9) + propargyl bromide (106-96-7) → 5-O-benzyl-1,2-O-isopropylidine-3-O-(2-propyn-1-yl)-α-D-xylofuranose (1612222-32-8)

Guidance literature:

5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.333333h; Inert atmosphere;

propargyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jo500890w

Reference yield:

C12H18O6 → 5-O-benzyl-1,2-O-isopropylidine-3-O-(2-propyn-1-yl)-α-D-xylofuranose (1612222-32-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium periodate / methanol / 4 h / 0 - 20 °C

1.2: 6 h / 0 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C

2.2: 6 h / 20 °C

With sodium periodate; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/jhet.2845

upstream raw materials:

5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

propargyl bromide

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

1,2;5,6-di-O-isopropylidine-3-O-(2-propyn-1-yl)-α-D-glucofuranose

Downstream raw materials:

6-(4-(5-O-benzyl-3-O-methylene-1,2-O-isopropylidene-α-D-xylofuranose)-1H-1,2,3-triazol-1-yl)-6,7-dihydro-4H-[1,2,3]triazolo[5,1-c][1,4]oxazine

3-azido-1-(4-(5-O-benzyl-3-O-methylene-1,2-O-isopropylidene-α-D-xylofuranose)-1H-1,2,3-triazol-1-yl)propan-2-ol