allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosiduronic acid

Base Information

• Chemical Name: allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosiduronic acid
• CAS No.: 117780-18-4
• Molecular Formula: C₂₅H₂₇ClO₈
• Molecular Weight: 490.938
• Mol file: 117780-18-4.mol

Synonyms:

Chemical Property of allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosiduronic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosiduronic acid

There total 7 articles about allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosiduronic acid 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: 46.0%

allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranoside (117780-16-2) → Chloro-acetic acid (2R,3S,4S,5R,6R)-6-allyloxy-4,5-bis-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (117780-17-3) + allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosiduronic acid (117780-18-4)

Guidance literature:

With jones reagent; In acetone; for 2h;

DOI:10.1016/S0008-6215(00)90828-0

Reference yield:

benzyl bromide (100-39-0) → allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosiduronic acid (117780-18-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 55.7 percent / 60 percent NaH / dimethylformamide / 1.) 1 h; 2.) 0.5 h, 0 deg C; 3.) 2.5 h, RT

2: 92.1 percent / 80 percent aq. AcOH / 1 h / 60 °C

3: pyridine / 3 h / Ambient temperature

4: pyridine / 3.5 h

5: 2 percent benzenesulfonic acid / CHCl₃; methanol / 0.5 h

6: 46 percent / 8 N Jones reagent / acetone / 2 h

With jones reagent; sodium hydride; acetic acid; benzenesulfonic acid; In pyridine; methanol; chloroform; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0008-6215(00)90828-0

Reference yield:

allyl 2,3-di-Ο-benzyl-β-D-galactopyranoside (97817-99-7) → allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosiduronic acid (117780-18-4)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 3 h / Ambient temperature

2: pyridine / 3.5 h

3: 2 percent benzenesulfonic acid / CHCl₃; methanol / 0.5 h

4: 46 percent / 8 N Jones reagent / acetone / 2 h

With jones reagent; benzenesulfonic acid; In pyridine; methanol; chloroform; acetone;

DOI:10.1016/S0008-6215(00)90828-0

upstream raw materials:

allyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranoside

benzyl bromide

allyl 2,3-di-Ο-benzyl-β-D-galactopyranoside

allyl 4,6-O-isopropylidene-β-D-galactopyranoside

Downstream raw materials:

methyl (2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl fluoride)uronate

methyl (2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosyl fluoride)uronate

methyl 2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranuronate

methyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranuronate