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

Base Information

• Chemical Name: methyl (2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl fluoride)uronate
• CAS No.: 117780-14-0
• Molecular Formula: C₂₃H₂₄ClFO₇
• Molecular Weight: 466.891
• Mol file: 117780-14-0.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about methyl (2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl fluoride)uronate 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:

benzyl bromide (100-39-0) → methyl (2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl fluoride)uronate (117780-14-0)

Guidance literature:

Multi-step reaction with 9 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

7: diethyl ether

8: NaOAc / PdCl₂ / aq. acetic acid / 30 - 35 °C / ultrasonication

9: diethylaminosulfur trifluoride / tetrahydrofuran / 0.5 h / Ambient temperature

With jones reagent; diethylamino-sulfur trifluoride; sodium acetate; sodium hydride; acetic acid; benzenesulfonic acid; palladium dichloride; In tetrahydrofuran; pyridine; methanol; diethyl ether; chloroform; acetic acid; 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) → methyl (2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl fluoride)uronate (117780-14-0)

Guidance literature:

Multi-step reaction with 7 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

5: diethyl ether

6: NaOAc / PdCl₂ / aq. acetic acid / 30 - 35 °C / ultrasonication

7: diethylaminosulfur trifluoride / tetrahydrofuran / 0.5 h / Ambient temperature

With jones reagent; diethylamino-sulfur trifluoride; sodium acetate; benzenesulfonic acid; palladium dichloride; In tetrahydrofuran; pyridine; methanol; diethyl ether; chloroform; acetic acid; acetone;

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

Reference yield:

allyl 2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranoside (117780-15-1) → methyl (2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl fluoride)uronate (117780-14-0)

Guidance literature:

Multi-step reaction with 8 steps

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

2: pyridine / 3 h / Ambient temperature

3: pyridine / 3.5 h

4: 2 percent benzenesulfonic acid / CHCl₃; methanol / 0.5 h

5: 46 percent / 8 N Jones reagent / acetone / 2 h

6: diethyl ether

7: NaOAc / PdCl₂ / aq. acetic acid / 30 - 35 °C / ultrasonication

8: diethylaminosulfur trifluoride / tetrahydrofuran / 0.5 h / Ambient temperature

With jones reagent; diethylamino-sulfur trifluoride; sodium acetate; acetic acid; benzenesulfonic acid; palladium dichloride; In tetrahydrofuran; pyridine; methanol; diethyl ether; chloroform; acetic acid; acetone;

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

upstream raw materials:

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

benzyl bromide

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

allyl 2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranoside