Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester
• CAS No.: 313360-59-7
• Molecular Formula: C₂₁H₂₆O₁₀
• Molecular Weight: 438.431
• Mol file: 313360-59-7.mol

Synonyms:Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester

Chemical Property of Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester

There total 3 articles about Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester 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:

3-O-benzyl-1,2-O-isopropylidene-α-D-galactofuranose (65434-49-3) → Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester (313360-59-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / pyridine; 4-(dimethylamino)pyridine / 1 h

2: CF₃CO₂H / CHCl₃ / 8 h

3: pyridine / 0.33 h

With pyridine; dmap; trifluoroacetic acid; In chloroform;

DOI:10.1021/ja001515t

Reference yield:

5,6-di-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-galactofuranose (313360-58-6) → Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester (313360-59-7)

Guidance literature:

Multi-step reaction with 2 steps

1: CF₃CO₂H / CHCl₃ / 8 h

2: pyridine / 0.33 h

With pyridine; trifluoroacetic acid; In chloroform;

DOI:10.1021/ja001515t

Reference yield:

acetic anhydride (108-24-7) + Acetic acid (R)-2-acetoxy-1-((2S,3R,4R)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-ethyl ester → Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-((R)-1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester (313360-59-7)

Guidance literature:

With pyridine; for 0.333333h;

DOI:10.1021/ja001515t

upstream raw materials:

acetic anhydride

3-O-benzyl-1,2-O-isopropylidene-α-D-galactofuranose

5,6-di-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-galactofuranose

Downstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl-(1->3)-1,2,5,6-tetra-O-acetyl-α,β-D-galactofuranose